13β-ethyl-11α-hydroxygon-5-ene-3,17-dione-3,17-diethylene ketal | 184778-59-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 13β-ethyl-11α-hydroxygon-5-ene-3,17-dione-3,17-diethylene ketal
• CAS: 184778-59-4
• 化学式: C₂₃H₃₄O₅
• 分子量: 390.52
• InChiKey: TYGRQMSAIWOGDB-XAYQJVIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  13β-ethyl-11α-hydroxygon-5-ene-3,17-dione-3,17-diethylene ketal 在 盐酸 、 sodium acetate 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 20.5h， 生成 13β-ethyl-11-methylenegon-4-en-3,17-dione
  参考文献：
  名称：

  An Improved Synthesis of 13β-Ethyl-11-methylenegon-4-en-3,17-dione

  摘要：

  An improved synthesis of 13 beta-ethyl-11-methylenegon-4-en-3,17-dione with the total yield of 57% starting from 13 beta-ethyl-11 alpha-hydroxy-gon-4-ene-3,17-dione is described.

  DOI：

  10.1080/00397919708006801
• 作为产物：
  描述：

  乙二醇 、 11a-羟基-18-甲基雌甾-4-烯-3,17-二酮 在 4-甲基苯磺酸吡啶 、 原甲酸三乙酯 作用下， 以 苯 为溶剂， 反应 6.0h， 以86%的产率得到13β-ethyl-11α-hydroxygon-5-ene-3,17-dione-3,17-diethylene ketal
  参考文献：
  名称：

  An Improved Synthesis of 13β-Ethyl-11-methylenegon-4-en-3,17-dione

  摘要：

  An improved synthesis of 13 beta-ethyl-11-methylenegon-4-en-3,17-dione with the total yield of 57% starting from 13 beta-ethyl-11 alpha-hydroxy-gon-4-ene-3,17-dione is described.

  DOI：

  10.1080/00397919708006801

文献信息

• Crystal structures of 10α-gon-5-enes from the synthetic pathway to desogestrel
  作者：E MODICA、D COLOMBO、F RONCHETTI、A SCALA、G BOMBIERI、N MARCHINI、L TOMA

  DOI：10.1016/j.steroids.2005.03.006

  日期：2005.8

  X-ray crystallographic studies performed on the product of the ketalization reaction of 13 beta-ethyl-11 alpha-hydroxy-gon-5-ene-3,17-dione have lead to the unequivocal assignment of the 10 alpha stereochemistry to C10, showing that an inversion of configuration occurred during formation of the 3,17-diketal. From the Swern oxidation of this compound, 11 alpha-(methylthio)methoxy-10 alpha-gonene was obtained as the major product instead of the desired 11-ketone. Modeling studies showed that the configurational instability at C 10 is determined by the presence of the 11 alpha-hydroxyl group. (c) 2005 Elsevier Inc. All rights reserved.