3,3-ethylenedioxy-5-β,10-β-epoxy-17-trimethylsilyloxyestra-9(11),16(17)-diene | 669003-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 3,3-ethylenedioxy-5-β,10-β-epoxy-17-trimethylsilyloxyestra-9(11),16(17)-diene
• 英文别名: trimethyl-[(1'S,5'S,9'S,10'S,13'S)-5'-methylspiro[1,3-dioxolane-2,15'-18-oxapentacyclo[11.4.1.01,13.02,10.05,9]octadeca-2,6-diene]-6'-yl]oxysilane
• CAS: 669003-25-2
• 化学式: C₂₃H₃₄O₄Si
• 分子量: 402.606
• InChiKey: CUZMYAMPVBCPIQ-VNTSLDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3-ethylenedioxy-5-β,10-β-epoxy-17-trimethylsilyloxyestra-9(11),16(17)-diene 在 盐酸 、 copper(l) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 11α-(4-(2-(diethylamino)-ethoxy)phenyl)estra-4,9-diene-3,17-dione
  参考文献：
  名称：

  Recent developments in the synthesis of 11β-aryl-estrone derivatives

  摘要：

  An industrial synthesis of 11beta-aryl-estrone derivatives is described, based on the 1,4-addition of the aryl side-chain, as a cuprate. oil to a mixture of allylic 5(10) alpha and beta epoxides, followed by hydrolysis and subsequent aromatization. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.028
• 作为产物：
  描述：

  三甲基氯硅烷 、 3-(ethylenedioxy)estra-5,10-epoxy-9(11)-ene-17-one 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 1.5h， 生成 3,3-ethylenedioxy-5,10-α-epoxy-17-(trimethylsilyloxy)-estra-9(11),16-diene 、 3,3-ethylenedioxy-5-β,10-β-epoxy-17-trimethylsilyloxyestra-9(11),16(17)-diene
  参考文献：
  名称：

  Industrial Synthesis of 4-Chloro,11β-arylestradiol: How to Circumvent a Poor Diastereoselectivity

  摘要：

  An industrial synthesis of 11beta-arylestrone derivatives is described, based on the conjugate opening of a mixture of allylic 5(10)-alpha and -beta epoxides by an aryl cuprate generated catalytically, followed by hydrolysis and subsequent aromatisation of the isomeric mixture of arylation products. An original method for selective 4-chlorination of estrone derivatives is also described.

  DOI：

  10.1021/op0341622

文献信息

• Novel method and intermediates for preparing 19-norsteroid compounds
  申请人：Aventis Pharma S.A.

  公开号：US20040229853A1

  公开（公告）日：2004-11-18

  The subject of the invention is a method for preparing compounds of general formula (I): 1 in which A, Z, R 3 are as defined in the description, and the intermediate compounds for carrying out this method.

  本发明的主题是一种制备一般式(I)化合物的方法：其中A、Z、R3如描述中所定义，并用于执行该方法的中间化合物。
• Industrial Synthesis of 4-Chloro,11β-arylestradiol: How to Circumvent a Poor Diastereoselectivity
  作者：Denis Prat、Françoise Benedetti、Gilles Franc Girard、Lahlou Nait Bouda、John Larkin、Christian Wehrey、Jacques Lenay

  DOI：10.1021/op0341622

  日期：2004.3.1

  An industrial synthesis of 11beta-arylestrone derivatives is described, based on the conjugate opening of a mixture of allylic 5(10)-alpha and -beta epoxides by an aryl cuprate generated catalytically, followed by hydrolysis and subsequent aromatisation of the isomeric mixture of arylation products. An original method for selective 4-chlorination of estrone derivatives is also described.
• Recent developments in the synthesis of 11β-aryl-estrone derivatives
  作者：Denis Prat、Françoise Benedetti、Lahlou Nait Bouda、Gilles Franc Girard

  DOI：10.1016/j.tetlet.2003.11.028

  日期：2004.1

  An industrial synthesis of 11beta-aryl-estrone derivatives is described, based on the 1,4-addition of the aryl side-chain, as a cuprate. oil to a mixture of allylic 5(10) alpha and beta epoxides, followed by hydrolysis and subsequent aromatization. (C) 2003 Elsevier Ltd. All rights reserved.