16.16α-Dimethyl-androsten-(5)-ol-(3β)-on-(17)-methylether | 55837-03-1

• 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: 16.16α-Dimethyl-androsten-(5)-ol-(3β)-on-(17)-methylether
• 英文别名: Androst-5-en-17-one, 3-methoxy-16,16-dimethyl-, (3beta)-；(3S,8R,9S,10R,13S,14S)-3-methoxy-10,13,16,16-tetramethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 55837-03-1
• 化学式: C₂₂H₃₄O₂
• 分子量: 330.511
• InChiKey: SXAQFQOOEQYFBW-ASOAYHERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  16.16α-Dimethyl-androsten-(5)-ol-(3β)-on-(17)-methylether 在 1,1,3,5-tetramethyl-4-oxo-2,6-diphenylpiperidinium (-)OTf Oxone 、 edetate disodium 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成 5β,6β-epoxy-16,16-dimethyl-3β-methoxyandrostan-17-one 、
  参考文献：
  名称：

  Highly β‐Selective Epoxidation of Δ ⁵ ‐Unsaturated Steroids Catalyzed by Ketones

  摘要：

  A general catalytic and environmentally friendly method for beta-epoxidation of Delta(5)-unsaturated steroids has been developed, which uses ketones as the catalysts and Oxone as the terminal oxidant. A whole range of Delta(5)-unsaturated steroids, which bear different functional groups such as hydroxyl, carbonyl, acetyl, or ketal, as well as different side chains, were conveniently converted to the corresponding synthetically and biologically interesting 5 beta,5 beta-epoxides with excellent beta-selectivities and high yields.

  DOI：

  10.1002/1521-3765(20001002)6:19<3517::aid-chem3517>3.0.co;2-#
• 作为产物：
  描述：

  去氢表雄酮 、 碘甲烷 生成 16.16α-Dimethyl-androsten-(5)-ol-(3β)-on-(17)-methylether
  参考文献：
  名称：

  WOLFLING, JANOS;SCHNEIDER, GYULA;DOMBI, GYORGY, STEROIDS, 51,(1988) N-4, C. 329-335

  摘要：

  DOI：

文献信息

• Method for synthesizing 5beta, 6beta-epoxides of steroids by a highly beta-selective epoxidation of delta5-unsaturated steroids catalyzed by ketones
  申请人：——

  公开号：US20030018188A1

  公开（公告）日：2003-01-23

  A general, efficient, and environmentally friendly method is provided for producing mostly &bgr;-epoxides of &Dgr; 5 -unsaturated steroids using certain ketones as the catalyst along with an oxidizing agent, or by using certain dioxiranes. In another aspect of the invention, a method is provided for producing mostly 5&bgr;,6&bgr;-epoxides of steroids from &Dgr; 5 -unsaturated steroids having a substituent at the 3&agr;-position by an epoxidation reaction using a ketone along with an oxidizing agent under conditions effective to generate epoxides, or using a dioxirane under conditions effective to generate epoxides. A whole range of &Dgr; 5 -unsaturated steroids, bearing different functional groups such as hydroxy, carbonyl, acetyl or ketal group as well as different side chains, were conveniently converted to the corresponding synthetically and biologically interesting 5&bgr;,6&bgr;-epoxides with excellent &bgr;-selectivities and high yields.

  提供了一种通用、高效且环保的方法，用于利用某些酮作为催化剂以及氧化剂，或者使用某些二氧杂环丙烷，生产大部分为&Dgr; 5 -不饱和类固醇的&bgr;-环氧化物。在发明的另一个方面，提供了一种方法，通过使用酮以及氧化剂进行环氧化反应，或者在有效条件下使用二氧杂环丙烷，从3&agr;-位有取代基的&Dgr; 5 -不饱和类固醇中生产大部分为5&bgr;,6&bgr;-环氧化物。一整套带有不同官能团（如羟基、酮基、乙酰基或缩醛基）以及不同侧链的&Dgr; 5 -不饱和类固醇，方便地转化为相应的合成和生物学上有趣的5&bgr;,6&bgr;-环氧化物，具有优异的&bgr;-选择性和高产率。
• Steroids 36: Synthesis of 16,16-dimethyl-17-ketosteroids and 16,16-dimethyl-17β-hydroxysteroids
  作者：Janos Wolfling、Gyula Schneider、Gyorgy Dombi

  DOI：10.1016/0039-128x(88)90022-0

  日期：1988.3

  Direct conversion of 17-ketosteroids (Ia-f) into 16,16-dimethyl-17 beta-hydroxysteroids (IIa-f) and 16,16-dimethyl-17-ketosteroids (IIIa-f) was achieved with methyl iodide in the presence of NaH.
• US6841665B2
  申请人：——

  公开号：US6841665B2

  公开（公告）日：2005-01-11
• [EN] METHOD FOR SYNTHESIZING 5ß, 6ß-EPOXIDES OF STEROIDS BY A HIGHLY ß-SELECTIVE EPOXIDATION OF DELTA5-UNSATURATED STEROIDS CATALYZED BY KETONES<br/>[FR] PROCEDE DE SYNTHESE DE 5 DOLLAR G(B),6 DOLLAR G(B)-EPOXYDES DE STEROIDES PAR EPOXYDATION HAUTEMENT DOLLAR G(B)-SELECTIVE DE STEROIDES DOLLAR G(D)5-INSATURES CATALYSES PAR DES CETONES
  申请人：UNIV HONG KONG

  公开号：WO2003074545A1

  公开（公告）日：2003-09-12

  A general, efficient, and environmentally friendly method is provided for producing mostly ß-epoxides of Δ5-unsaturated steroids using certain ketones as the catalyst along with an oxidizing agent, or by using certain dioxiranes. In another aspect of the invention, a method is provided for producing mostly 5ß, 6ß-epoxides of steroids from Δ5-unsaturated steroids having a substituent at the 3α-position by an epoxidation reaction using a ketone along with an oxidizing agent under conditions effective to generate epoxides, or using a dioxirane under conditions effective to generate epoxides. A whole range of Δ5-unsaturated steroids, bearing different functional groups such as hydroxy, carbonyl, acetyl of ketal group as well as different side chains, were conveniently converted to the corresponding synthetically and biologically interesting 5ß, 6ß-epoxides with excellent ß-selectivities and high yields.
• Highly β‐Selective Epoxidation of Δ ⁵ ‐Unsaturated Steroids Catalyzed by Ketones
  作者：Dan Yang、Guan‐Sheng Jiao

  DOI：10.1002/1521-3765(20001002)6:19<3517::aid-chem3517>3.0.co;2-#

  日期：2000.10.2

  A general catalytic and environmentally friendly method for beta-epoxidation of Delta(5)-unsaturated steroids has been developed, which uses ketones as the catalysts and Oxone as the terminal oxidant. A whole range of Delta(5)-unsaturated steroids, which bear different functional groups such as hydroxyl, carbonyl, acetyl, or ketal, as well as different side chains, were conveniently converted to the corresponding synthetically and biologically interesting 5 beta,5 beta-epoxides with excellent beta-selectivities and high yields.