3β-cyanoandrost-3-one-17β-ol | 17521-61-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β-cyanoandrost-3-one-17β-ol
• 英文别名: 17β-Hydroxy-3-oxo-5β-androstan-5-carbonitril；5β-Cyan-17β-hydroxy-androstanon-(3)
• CAS: 17521-61-8
• 化学式: C₂₀H₂₉NO₂
• 分子量: 315.456
• InChiKey: FYXFHBLBSLNOGN-ZYRLFZHTSA-N

物化性质

• 沸点：
  475.3±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  61.09
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5β-cyano-3-O-(α-D-glucopyranosyl)androst-4-ene-17β-ol 在 硫酸 作用下， 反应 18.0h， 以60.5%的产率得到3β-cyanoandrost-3-one-17β-ol
  参考文献：
  名称：

  Cyanoglycosylation products of 17-O-acetyl-testosterone

  摘要：

  17-O-Acetyl testosterone, which has no susceptible hydroxyl or carboxyl group for glycosylation, was glycosylated with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide in the presence of a mixed catalyst, Hg(CN)(2) and HgBr2, in benzene-nitromethane. Reaction occurred on the alpha, beta-unsaturated ketone on the six-membered A-ring to give six 3-O-glycosides, each bearing a cyano group at the 3- or 5-position of the aglycon, and a 3-O-glycoside bearing a CONH2 group at the 3-position. Structural analyses of these products were carried out by various NMR (H-1, C-13 NMR,H-1-H-1 and H-1-C-13 COSY, HMBC; and DEFT), FARMS and X-ray analyses. The mechanisms of the formations of the products are discussed. It was determined that mercuric cyanide was essential as a catalyst for the progress of the cyanoglycosylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00192-x

文献信息

• Hydrocyanation. VI. Application of the new hydrocyanation methods to conjugate hydrocyanation of .alpha.,.beta.-unsaturated ketones, conjugated dienones, and conjugated enamines and to preparation of .alpha.-cyanohydrins
  作者：W. Nagata、M. Yoshioka、M. Murakami

  DOI：10.1021/ja00768a039

  日期：1972.6
• Stereochimie-LV
  作者：C. Agami、M. Fadlallah、J. Levisalles、P. Cayzergues

  DOI：10.1016/s0040-4020(01)98904-5

  日期：1981.1