The Reaction of 8-Amino-p-menthene Derivatives with Electrophiles

2004 ◽  
Vol 57 (6) ◽  
pp. 583
Author(s):  
Paul V. Bernhardt ◽  
Raymond M. Carman ◽  
Roger P. C. Derbyshire
Keyword(s):  
Double Bond ◽  
Nitrogen Atom ◽  
The Novel

Attempts to ring-close the nitrogen atom of 8-amino-p-menth-1-ene and of N-substituted 8-amino-p-menth-1-enes onto the C1–C2 double-bond carbons has led to a range of bicyclo[2.2.2] and bicyclo[3.2.1] products, together with the novel bicyclo[4.3.1]-1,3-oxazepine 9.

Configuration on the C=N double bond of monosubstituted amidines and amidoximes

1989 ◽  
Vol 54 (12) ◽  
pp. 3245-3252 ◽  
Author(s):  
Bernard Tinant ◽  
Janine Dupont-Fenfau ◽  
Jean-Paul Declercq ◽  
Jaroslav Podlaha ◽  
Otto Exner
Keyword(s):  
Double Bond ◽  
Nitrogen Atom ◽  
Steric Effects ◽  
Model Compounds ◽  
X Ray ◽  
Analogous Model

Configuration on the C=N double bond of amidines and amidoximes is controlled by steric effects on the second nitrogen atom but there is a difference in the case of N’-monosubstituted derivatives: amidines prefer E configuration (conformation around the C-N bond sp) and amidoximes Z configuration (conformation ap). This was confirmed by the X-ray structures of two analogous model compounds N,N’-dimethyl-4-nitrobenzamidine (monoclinic, P21c, a = 10.855(3), b = 11.043(3), c = 8.593(3) Å, β = 105.69(2)°, V = 991.8(5) Å3, Z = 4, Dx = 1.29 g cm-3, CuKα, λ = 1.5418 Å, μ = 7.91 cm-1, F(000) = 408, T = 291 K, R = 0.065 for 1 265 observed reflections) and N’-methyl-4-nitrobenzamidoxime (monoclinic, P21/a, a = 6.699(2), b = 24.178(9), c = 6.075(2) Å, β = 106.20(3)°, V = 944.9(6) Å3, Z = 4, Dx = 1.37 g cm-3, CuKα, λ = 1.5418 Å, μ =9.22 cm-1, F(000) = 408, T = 291 K, R = 0.079 for 1 278 observed reflections).

Porcine glutathione transferase Alpha 2-2 is a human GST A3-3 analogue that catalyses steroid double-bond isomerization

2010 ◽  
Vol 431 (1) ◽  
pp. 159-167 ◽  
Author(s):  
Natalia Fedulova ◽  
Françoise Raffalli-Mathieu ◽  
Bengt Mannervik
Keyword(s):  
Double Bond ◽  
Glutathione Transferase ◽  
Biological Species ◽  
Glutathione Transferases ◽  
Special Role ◽  
Primary Role ◽  
The Novel ◽  
Protective Function ◽  
Isomerase Activity

A primary role of GSTs (glutathione transferases) is detoxication of electrophilic compounds. In addition to this protective function, hGST (human GST) A3-3, a member of the Alpha class of soluble GSTs, has prominent steroid double-bond isomerase activity. The isomerase reaction is an obligatory step in the biosynthesis of steroid hormones, indicating a special role of hGST A3-3 in steroidogenic tissues. An analogous GST with high steroid isomerase activity has so far not been found in any other biological species. In the present study, we characterized a Sus scrofa (pig) enzyme, pGST A2-2, displaying high steroid isomerase activity. High levels of pGST A2-2 expression were found in ovary, testis and liver. In its functional properties, other than steroid isomerization, pGST A2-2 was most similar to hGST A3-3. The properties of the novel porcine enzyme lend support to the notion that particular GSTs play an important role in steroidogenesis.

THE REACTION OF ACTIVE NITROGEN WITH PROPYLENE

1952 ◽  
Vol 30 (12) ◽  
pp. 915-921 ◽  
Author(s):  
G. S. Trick ◽  
C. A. Winkler
Keyword(s):  
Double Bond ◽  
Nitrogen Atom ◽  
Hydrogen Cyanide ◽  
Atomic Hydrogen ◽  
Atomic Nitrogen ◽  
Active Nitrogen

The reaction of nitrogen atoms with propylene has been found to produce hydrogen cyanide and ethylene as the main products, together with smaller amounts of ethane and propane and traces of acetylene and of a C4 fraction. With excess propylene, the nitrogen atoms were completely consumed and for the reaction at 242 °C., 0.77 mole of ethylene was produced for each mole of excess propylene added. For reactions at lower temperatures, less ethylene was produced. The proposed mechanism involves formation of a complex between the nitrogen atom and the double bond of propylene, followed by decomposition to ethylene, hydrogen cyanide, and atomic hydrogen. The ethylene would then react with atomic nitrogen in a similar manner.

The effect of nitrogen atom on double bond pyramidalization

2004 ◽  
Vol 34 (7) ◽  
pp. 477-481 ◽  
Author(s):  
Recep Özen ◽  
Kutalmis Guven ◽  
Hatice Can ◽  
Metin Balci
Keyword(s):  
Double Bond ◽  
Nitrogen Atom

scholarly journals Die Kristallstruktur von PPh3Me[NbOCl4(CH3CN)] / The Crystal Structure of PPh3Me[NbOCl4(CH3CN)]

1984 ◽  
Vol 39 (1) ◽  
pp. 107-110 ◽  
Author(s):  
W. Hiller ◽  
J. Strähle ◽  
H. Prinz ◽  
K. Dehnicke
Keyword(s):  
Crystal Structure ◽  
Double Bond ◽  
Nitrogen Atom ◽  
Bond Length ◽  
Unit Cell ◽  
Trans Position ◽  
Space Group ◽  
X Ray ◽  
Oxo Ligand ◽  
Solvate Molecule

The X-ray structure of PPh3Me[NbOCl4(CH3CN)] at 210 K was solved (space group P1̄, two formula units per unit cell, a = 1173.5(5), b = 1130.1(4), c = 946.8(3) pm, α = 97.70(4), β = 93.57(3), γ = 78.62(3)°, 3688 inde­pendent reflexions, R = 0.025). The material consists of cations [P(C6H5)3CH3]⊕ and anions [NbOCl4(CH3CN)]⊖. The nitrogen atom of the acetonitrile solvate molecule is coordinated to the niobium centre in the trans-position to the oxo ligand; the NbO bond length of 169 pm corresponds to a double bond.

scholarly journals Further Studies on Structure-Cardiac Activity Relationships of Diterpenoid Alkaloids

2015 ◽  
Vol 10 (12) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Zhong-Tang Zhang ◽  
Xi-Xian Jian ◽  
Jia-Yu Ding ◽  
Hong-Ying Deng ◽  
Ruo-Bing Chao ◽  
...  
Keyword(s):  
Double Bond ◽  
Nitrogen Atom ◽  
Cardiac Activity ◽  
Structural Features ◽  
Cardiac Effect ◽  
Diterpenoid Alkaloids ◽  
Heart Model ◽  
Reference Drug ◽  
Cardiac Action ◽  
Type C

The cardiac effect of thirty-eight diterpenoid alkaloids was evaluated on the isolated bullfrog heart model. Among them, twelve compounds exhibited appreciable cardiac activity, with compounds 3 and 35 being more active than the reference drug lanatoside. The structure-cardiac activity relationships of the diterpenoid alkaloids were summarized based on our present and previous studies [2]: i) 1α-OMe or 1α-OH, 8-OH, 14-OH, and NH (or NMe) are key structural features important for the cardiac effect of the aconitine-type C19-diterpenoid alkaloids without any esters. C18-diterpenoid alkaloids, lycoctonine-type C19-diterpenoid alkaloids, and the veatchine- and denudatine-type C20-diterpenoid alkaloids did not show any cardiac activity; ii) the presence of 3α-OH is beneficial to the cardiac activity; iii) the effect on the cardiac action of 6α-OMe, 13-OH, 15α-OH, and 16-demethoxy or a double bond between C-15 and C-16 depends on the substituent pattern on the nitrogen atom.

Silver(I)-Catalyzed Deprenylation of Allylsulfonamide Derivatives

Synlett ◽  
2017 ◽  
Vol 28 (16) ◽  
pp. 2143-2146 ◽  
Author(s):  
Fuyuhiko Inagaki ◽  
Shisen Hira ◽  
Chisato Mukai
Keyword(s):  
Double Bond ◽  
Nitrogen Atom ◽  
Functional Groups ◽  
Silver Cation ◽  
Elimination Reaction

The silver(I)-catalyzed deprenylation of sulfonamide bearing prenyl functional groups on the nitrogen atom has been developed. In this reaction, the prenyl moiety was selectively eliminated without allyl or benzyl cleavage on the nitrogen atom. In addition, geranyl was also applicable for this elimination reaction. Furthermore, sulfonamide possessing two prenyl groups underwent a double deprenylation to form the corresponding deprenylated sulfonamide. Thus, a novel reactivity between the silver cation and double bond was observed.

LYCOPODIUM ALKALOIDS: XVI. ANNOTINE

1964 ◽  
Vol 42 (11) ◽  
pp. 2584-2594 ◽  
Author(s):  
W. A. Szarek ◽  
K. A. H. Adams ◽  
M. Curcumelli-Rodostamo ◽  
D. B. MacLean
Keyword(s):  
Double Bond ◽  
Nitrogen Atom ◽  
Hydroxyl Group ◽  
Tertiary Nitrogen Atom ◽  
Chemical Studies ◽  
Group A ◽  
Instrumental Methods ◽  
Tertiary Hydroxyl ◽  
Plausible Structure ◽  
Tertiary Nitrogen

Annotine, C16H21O3N, is shown to be pentacyclic and to contain a tertiary hydroxyl group, a lactone function, a tertiary nitrogen atom, and a dialkylated double bond. The position of the double bond and the tertiary hydroxyl group relative to the nitrogen atom has been established by Emde degradation of annotine methiodide. The presence of a lactone function is inferred from the reduction of annotine to dihydroannotinol, a hemiacetal, which reacts with 1 mole of ethyl mercaptan. The reduction of the lactone to a diol in an annotine derivative has been carried out. The chemical studies and the examination of annotine and its derivatives by modern instrumental methods allow the assignment of a plausible structure to the alkaloid.

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