stigmast-4,22-dien-3β,6β-diol | 167958-89-6

• 物质功能分类: 天然产物 - 甾体化合物
• 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: stigmast-4,22-dien-3β,6β-diol
• 英文别名: stigmasta-4,22-diene-3β,6β-diol；stigmastadiene-(4,22t)-diol-(3β,6β)；24α_F-Aethyl-cholestadien-(4,22t)-diol-(3β,6β)；3β,6β-Dihydroxy-10,13-dimethyl-17β-((1R:4S)-1,5-dimethyl-4-aethyl-hexen-(2t)-yl)-gonen-(4)；(10R)-3c.6c-Dihydroxy-10r,13c-dimethyl-17c-((1R:4S)-1,5-dimethyl-4-aethyl-hexen-(2t)-yl)-(8cH,9tH,14tH)-Δ⁴-tetradecahydro-1H-cyclopenta[a]phenanthren；(24S)-24-Aethyl-cholestadien-(4,22t)-diol-(3β,6β)；Stigmastadien-(4,22t)-diol-(3β,6β)；(3S,6R,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol
• CAS: 167958-89-6
• 化学式: C₂₉H₄₈O₂
• 分子量: 428.699
• InChiKey: YLQCVNVIULEHRQ-YIWILWCSSA-N

物化性质

• 沸点：
  535.7±38.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙醚 、 stigmast-4,22-dien-3β,6β-diol 、 溶剂黄146 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (5alpha)-豆甾烷
  参考文献：
  名称：

  Mitsui, Nippon Nogeikagaku Kaishi, 1939, vol. 15, p. 795,798, 801

  摘要：

  DOI：
• 作为产物：
  描述：

  豆甾醇 在 sodium tetrahydroborate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 stigmast-4,22-dien-3β,6β-diol
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (III): synthesis and structural elucidation of 24-methylenecholest-4-en-3β,6α-diol

  摘要：

  Using stigmasterol as the starting material, 24-methylenecholest-4-en-3beta,6alpha-diol (2) was synthesized in eight steps in 13% overall yield. The introduction of the sterol side-chain was carried out using (3-methyl-2-oxobutyl)-triphenylarsonium bromide (11) and K2CO3 in a solid-liquid phase-transfer Wittig reaction. Construction of the steroidal nucleus was finished by oxidation of 24-methylenecholest-5-en-3beta-ol (9) with pyridinium chlorochromate (PCC) in dichloromethane at ambient temperature and by reduction of 24-methylenecholest-4-en-3,6-dione (10) with NaBH4 in the presence of CeCl3.7H(2)O. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00059-4

文献信息

• Sterol compound and method of obtaining same
  申请人：PARKE DAVIS & CO

  公开号：US02227839A1

  公开（公告）日：1941-01-07
• Sterols. XXXII. Oxidation of Stigmasterol by Selenium Oxide
  作者：Russell E. Marker、Ewald Rohrmann

  DOI：10.1021/ja01272a025

  日期：1938.5
• Centurion, Osvaldo M. Teme; Galagovsky, Lydia R.; Gros, Eduardo G., Steroids, 1995, vol. 60, # 7, p. 504 - 508
  作者：Centurion, Osvaldo M. Teme、Galagovsky, Lydia R.、Gros, Eduardo G.

  DOI：——

  日期：——
• Mitsui, Nippon Nogeikagaku Kaishi, 1939, vol. 15, p. 795,798, 801
  作者：Mitsui

  DOI：——

  日期：——
• Synthesis of polyhydroxysterols (III): synthesis and structural elucidation of 24-methylenecholest-4-en-3β,6α-diol
  作者：Jian Guo Cui、Cui Wu Lin、Long Mei Zeng、Jing Yu Su

  DOI：10.1016/s0039-128x(02)00059-4

  日期：2002.12

  Using stigmasterol as the starting material, 24-methylenecholest-4-en-3beta,6alpha-diol (2) was synthesized in eight steps in 13% overall yield. The introduction of the sterol side-chain was carried out using (3-methyl-2-oxobutyl)-triphenylarsonium bromide (11) and K2CO3 in a solid-liquid phase-transfer Wittig reaction. Construction of the steroidal nucleus was finished by oxidation of 24-methylenecholest-5-en-3beta-ol (9) with pyridinium chlorochromate (PCC) in dichloromethane at ambient temperature and by reduction of 24-methylenecholest-4-en-3,6-dione (10) with NaBH4 in the presence of CeCl3.7H(2)O. (C) 2002 Elsevier Science Inc. All rights reserved.