6β-Hydroxy-3α.5α-cyclo-androstan-17-on | 663-39-8

• 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-Hydroxy-3α.5α-cyclo-androstan-17-on
• 英文别名: 6β-Hydroxy-3α,5-cyclo-5α-androstan-17-on；6beta-Hydroxy-3alpha,5alpha-cycloandrostan-17-one；(1S,2R,5R,7R,8R,10R,11S,15S)-8-hydroxy-2,15-dimethylpentacyclo[8.7.0.02,7.05,7.011,15]heptadecan-14-one
• CAS: 663-39-8
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: NIDVKCKYZAQGOI-BTAVXEMNSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6β-Hydroxy-3α.5α-cyclo-androstan-17-on 在 sterile acidic medium 作用下， 反应 192.0h， 生成 去氢表雄酮
  参考文献：
  名称：

  Cephalosporium aphidicola对3α,5-环雄甾烷的微生物羟基化作用

  摘要：

  真菌 Cephalosporium aphidicola 对某些 3α,5-环雄甾烷的微生物羟基化作用已显示在 C-2α 和 C-14α 处发生，并且 6β-醇被氧化为 6-酮。

  DOI：

  10.1016/s0031-9422(99)00415-x
• 作为产物：
  描述：

  去氢表雄酮 在 甲基磺酰氯 、 水 、 sodium acetate 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 44.0h， 以65%的产率得到6β-Hydroxy-3α.5α-cyclo-androstan-17-on
  参考文献：
  名称：

  摘要：

  Convenient methods for preparing several 3 alpha ,5-cycloandrostanes have been developed in order to synthesize the phytoecdysteroid rubrosterone. Certain of their chemical transformations were studied.

  DOI：

  10.1023/a:1017698325815

文献信息

• Steroid Series. XVI. The Preparation of 3α, 5α-Cyclo-6β, 19-oxidosteroids and its Conversion to 19-Oxygenated Steroid Derivatives
  作者：Katsumi Tanabe、Rinji Takasaki、Kiyoshi Sakai、Ryozo Hayashi、Yasuhiro Morisawa、Teruo Hashimoto

  DOI：10.1248/cpb.15.15

  日期：——

  3α, 5α-Cyclo-6β, 19-oxidosteroid (II) was synthesized by the lead tetraacetate oxidation of 3α, 5α-cyclo-6β-hydroxysteroid (I) in benzene. The acid-catalysed solvolysis of the oxide (II) afforded 3α, 5α-cyclo-19-hydroxy-6β-substituted steroid (XVI) and/or Δ5-19-hydroxy-3β-substituted steroid (XVII), depending upon the reaction conditions employed. Oxidation of the oxide (II) with Jones reagent gave 3α, 5α-cyclo-6β, 19-dioxosteroid (XIX) with two equivalent molar oxidant, and 3α, 5α-cyclo-6-oxosteroid-19-oic acid (XX) with the excess reagent.

  3α, 5α-环-6β, 19-氧化类固醇(II)是通过四乙酸铅在苯中氧化3α, 5α-环-6β-羟基类固醇(I)合成的。氧化物(II)的酸催化溶剂解提供3α，5α-环-19-羟基-6β-取代的类固醇(XVI)和/或Δ5-19-羟基-3β-取代的类固醇(XVII)，取决于反应采用的条件。用琼斯试剂氧化氧化物(II)，得到3α，5α-环-6β，19-二氧类固醇(XIX)和两个当量摩尔氧化剂，以及3α，5α-环-6-氧类固醇-19-油酸(XX)多余的试剂。
• Analytical Chemical Studies on Steroids. VII. The Zimmermann Complexes Derived from i-Androstanolone and Its Related 17-Oxosteroids
  作者：Toshio Nambara、Motohiko Kato

  DOI：10.1248/cpb.13.1435

  日期：——

  The structure of Zimmermann complexes produced from i-androstanolone (6β-hydroxy-3α, 5α-cycloandrostan-17-one) was investigated. By means of preparative thinlayer chromatography two complexes were successfully isolated and were elucidated as 6β-hydroxy-16ξ-(2, 4-dinitrophenyl)-3α, 5α-cycloandrostan-17-one, m.p. 113∼116°, and 3β-chloro-16ξ-(2, 4-dinitrophenyl)androst-5-en-17-one, m.p. 192∼194°, respectively. These results revealed that the former complex would be transformed into the latter one by contact with hydrochloric acid. On the other hand dehydroisoandrosterone gave Zimmermann complex, 3β-hydroxy-16ξ-(2, 4-dinitrophenyl)androst-5-en-17-one, m.p. 186∼188°, as a single product.

  研究了由i-雄甾烷酮（6β-羟基-3α，5α-环雄甾-17-酮）生成的齐默尔曼复合物的结构。通过制备薄层色谱法，成功分离出两种复合物，并分别阐明其为 6β-hydroxy-16ξ-(2, 4-dinitrophenyl)-3α, 5α-cycloandrostan-17-one, m.p. 113∼116° 和 3β-chloro-16ξ-(2, 4-dinitrophenyl)androst-5-en-17-one, m.p. 192∼194°。这些结果表明，前一种复合物与盐酸接触后会转化为后一种复合物。另一方面，脱氢异雄酮生成的齐默尔曼复合物为 3β-羟基-16ξ-（2，4-二硝基苯基）雄-5-烯-17-酮，熔点为 186∼188°。
• 291. A modified procedure for the preparation of 3,5-cyclosteroids
  作者：M. S. Patel、W. J. Peal

  DOI：10.1039/jr9630001544

  日期：——
• Microbial oxygenation of 6β-hydroxy-3α,5-cyclo-5α-androstan-17-one with Rhizopus nigricans
  作者：Ž. Procházka、M. Buděšínský、P. Prekajski

  DOI：10.1135/cccc19740982

  日期：——
• Modified steroid hormones—XLIX
  作者：D. Burn、F.K. Butcher、A. Cole、R.A. Coombs、M.T. Davies、M.J. Green、V. Petrow

  DOI：10.1016/s0040-4020(01)92611-0

  日期：1968.1