6β-chloro-5α-cholestanediol-(3β.5) | 3751-10-8

• 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: 6β-chloro-5α-cholestanediol-(3β.5)
• 英文别名: (10R)-6c-Chlor-3c.5t-dihydroxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；6β-Chlor-3β.5-dihydroxy-10.13-dimethyl-17β-((R)-1.5-dimethyl-hexyl)-5α-gonan；6β-Chlor-5α-cholestandiol-(3β.5)；6β-chlorocholestane-3β,-5α-diol；6beta-Chlorocholestan-3beta,5alpha-diol；(3S,5R,6R,8S,9S,10R,13R,14S,17R)-6-chloro-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,5-diol
• CAS: 3751-10-8
• 化学式: C₂₇H₄₇ClO₂
• 分子量: 439.122
• InChiKey: QWNZCMIFFKSIGR-RUXQDQFYSA-N

物化性质

• 熔点：
  173-174 °C(Solv: ethyl acetate (141-78-6); methanol (67-56-1))
• 沸点：
  529.5±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  6β-chloro-5α-cholestanediol-(3β.5) 在 chromium(VI) oxide 、 盐酸 、 magnesium sulfate 作用下， 以 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 反应 2.5h， 生成 3-oxocholest-4-en-6β-yl chloride
  参考文献：
  名称：

  Synthesis of some analogues of blattellastanoside A, the steroidal aggregation pheromone of the German cockroach

  摘要：

  Blattellastanoside A, the aggregation pheromone of the German cockroach, is a chlorinated steroid glucoside with the 5 beta-stigmastane skeleton. Its analogues were synthesized in order to clarify the structure-activity relationship. They are 1a with the 5 beta-cholestane skeleton, 1b with the 5 beta-androstane skeleton, Ic with a fluorine substituent instead of the chlorine and Id with a beta-D-galactopyranose instead of the beta-D-glucopyranose of the original pheromone. Their bioassay shows that la and Ic are active, while Ib and Id are totally devoid of pheromone activity. The aglycone of blattellastanosides A and B were active. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00018-1
• 作为产物：
  描述：

  5,6-epoxycholesterol 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 6β-chloro-5α-cholestanediol-(3β.5)
  参考文献：
  名称：

  Synthesis of some analogues of blattellastanoside A, the steroidal aggregation pheromone of the German cockroach

  摘要：

  Blattellastanoside A, the aggregation pheromone of the German cockroach, is a chlorinated steroid glucoside with the 5 beta-stigmastane skeleton. Its analogues were synthesized in order to clarify the structure-activity relationship. They are 1a with the 5 beta-cholestane skeleton, 1b with the 5 beta-androstane skeleton, Ic with a fluorine substituent instead of the chlorine and Id with a beta-D-galactopyranose instead of the beta-D-glucopyranose of the original pheromone. Their bioassay shows that la and Ic are active, while Ib and Id are totally devoid of pheromone activity. The aglycone of blattellastanosides A and B were active. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00018-1

文献信息

• Trans 1,2-functionalization of cycloalkenes using selenium intermediates
  作者：P. Ceccherelli、M. Curini、M.C. Marcotullio、O. Rosati

  DOI：10.1016/s0040-4039(00)99194-9

  日期：——

  The reaction of excess phenylselenenyl halides with trisubstituted cyclic olefins in aqueous acetonitrile is regio- and stereospecific and affords halohydrins in excellent yields. The reaction proceeds through the formation of a β-hydroxyalkyl phenyl selenide which evolves to halohydrin presumably an epoxy-intermediate.

  过量的苯基硒烯基卤化物与三取代的环烯烃在乙腈水溶液中的反应具有区域和立体特异性，并以优异的产率提供卤代醇。反应通过形成β-羟烷基苯基硒化物而进行，该β-羟烷基苯基硒化物发展为卤代醇，大概是环氧中间体。
• Meiosis regulating compounds
  申请人：——

  公开号：US20010005757A1

  公开（公告）日：2001-06-28

  Certain compounds, structurally related to natural compounds which can be extracted i.a. from bull testes and from human follicular fluid, can be used for regulating the meiosis in oocytes and in male germ cells. Some of these compounds are useful in the treatment of infertility, whereas other compounds are useful as contraceptives. These compounds have the structural formula 1 wherein the substituents are as defined in the specification.

  某些化合物在结构上与可以从公牛睾丸和人类卵泡液中提取的天然化合物相关，可用于调节卵母细胞和男性生殖细胞中的减数分裂。其中一些化合物对治疗不孕症有用，而其他化合物则可用作避孕药。这些化合物具有结构式，其中取代基如规范中定义。
• Hattori, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1940, vol. 60, p. 334,338; engl. Ref. S. 125
  作者：Hattori

  DOI：——

  日期：——
• Kocovsky,P.; Cerny,V., Collection of Czechoslovak Chemical Communications, 1977, vol. 42, p. 155 - 162
  作者：Kocovsky,P.、Cerny,V.

  DOI：——

  日期：——
• Stereochemistry of the Cholesterol Dichlorides¹
  作者：D. H. R. Barton、E. Miller

  DOI：10.1021/ja01157a100

  日期：1950.1