5β,17α-Dimethyl-estran-3β,17-diol | 56006-67-8

• 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: 5β,17α-Dimethyl-estran-3β,17-diol
• CAS: 56006-67-8
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: IZVBGNMSSDDJER-HESXETMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5β,17α-Dimethyl-estran-3β,17-diol 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以81%的产率得到17β-hydroxy-5,17-dimethyl-19-nor-5β,9α,10β-androstan-3-one
  参考文献：
  名称：

  Analogues of androgen hormones with inverted configuration at carbons 5, 9, and 10

  摘要：

  On catalytic hydrogenation of Delta (9)-steroids (e.g. 3 beta -hydroxy-5-methyl-19-nor-5 beta -androst-9-en-17-one), four isomers were formed: 9 alpha ,10 alpha-, 9 alpha ,10 beta-, 9 beta ,10 alpha- and 9 beta ,10 beta -adducts. The product distribution was affected by the nature of the C-3 substituent. A chair conformation of A, B, and C rings was found in all of the products with the exception of the 9 alpha ,10 alpha -adduct whose B ring adopts a twist boat conformation. The products were utilized for the synthesis of dihydrotestosterone analogues. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00135-0
• 作为产物：
  描述：

  5-methyl-17-oxo-19-nor-5β-androst-9-en-3β-yl acetate 在 platinum(IV) oxide jones reagent 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 乙醇 、 溶剂黄146 、 丙酮 、 苯 为溶剂， 反应 23.67h， 生成 5β,17α-Dimethyl-estran-3β,17-diol
  参考文献：
  名称：

  Analogues of androgen hormones with inverted configuration at carbons 5, 9, and 10

  摘要：

  On catalytic hydrogenation of Delta (9)-steroids (e.g. 3 beta -hydroxy-5-methyl-19-nor-5 beta -androst-9-en-17-one), four isomers were formed: 9 alpha ,10 alpha-, 9 alpha ,10 beta-, 9 beta ,10 alpha- and 9 beta ,10 beta -adducts. The product distribution was affected by the nature of the C-3 substituent. A chair conformation of A, B, and C rings was found in all of the products with the exception of the 9 alpha ,10 alpha -adduct whose B ring adopts a twist boat conformation. The products were utilized for the synthesis of dihydrotestosterone analogues. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00135-0

文献信息

• 1,4-Addition of vinylmagnesium bromide to .ALPHA.,.BETA.-unsaturated steroidal ketones. I. Reaction of 16-en-20-oxo and 19-nor-4-en-3-oxo steroids.
  作者：HIROMU MORI、RIKIO OHUCHI

  DOI：10.1248/cpb.23.559

  日期：——

  The reaction of 16-en-20-oxo and 19-nor-4-en-3-oxo steroids with vinylmagnesium bromide in the presence of cupric acetate afforded 16α-vinyl-20-oxo and 19-nor-5β-vinyl-3-oxo steroids. In order to establish the configuration of vinyl group introduced by the reaction and to study the streochemical relationship between the reaction with vinylmagnesium bromide and that with a saturated Grignard reagent, some transformations of vinyl compounds derived by the reaction were undertaken. The stereochemical course of reactions was found to be identical with that of a saturated Grignard reagent.

  在铜醋酸盐存在下，16-烯-20-氧代和19-诺尔-4-烯-3-氧代甾体与乙烯镁溴反应，生成了16α-乙烯基-20-氧代和19-诺尔-5β-乙烯基-3-氧代甾体。为了确定反应引入的乙烯基的构型，并研究乙烯镁溴反应与饱和Grignard试剂反应之间的立体化学关系，进行了一些由反应衍生的乙烯基化合物的转化。发现反应的立体化学过程与饱和Grignard试剂的反应过程相同。
• 1,4-Addition of vinylmagnesium bromide to .ALPHA.,.BETA.-unsaturated steroidal ketones. II. Reaction of 1-En-3-oxo steroids.
  作者：HIROMU MORI、RIKIO OHUCHI

  DOI：10.1248/cpb.23.980

  日期：——

  The reaction of 1-en-3-oxo A/B trans steroid with vinylmagnesium bromide in the presence of cupric acetate afforded 1α-vinyl-3-oxo steroid. The configuration of the vinyl group introduced by the reaction was found to be α-oriented by the transformation of II into the lactone (VIII). The stereochemistry of the reduction of 1α-alkyl-3-oxo steroids and 5β-alkyl-3-oxo steroids with complex metal hydride was also studied.

  1-en-3-oxo A/B 反式类固醇与乙烯基溴化镁在乙酸铜存在下反应，生成 1α-vinyl-3-oxo 类固醇。通过将 II 转化为内酯 (VIII)，发现反应中引入的乙烯基的构型为 α 向。此外，还研究了用复合金属氢化物还原 1α- 烷基-3-氧代甾族化合物和 5β- 烷基-3-氧代甾族化合物的立体化学过程。