3-苄氧基-4-羟基-17,17-亚乙二氧基-1,3,5(10)-雌三烯-6-酮乙酸酯 | 360771-94-4

• 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
• 中文名称: 3-苄氧基-4-羟基-17,17-亚乙二氧基-1,3,5(10)-雌三烯-6-酮乙酸酯
• 英文名称: 3-benzyloxy-4-hydroxy-17,17-ethylenedioxy-1,3,5(10)-estratrien-6-one acetate
• CAS: 360771-94-4
• 化学式: C₂₉H₃₂O₆
• 分子量: 476.569
• InChiKey: GTDVFNXGGMWSLM-WUDFOMDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-苄氧基-4-羟基-17,17-亚乙二氧基-1,3,5(10)-雌三烯-6-酮乙酸酯 在 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 11.5h， 生成 3-苄氧基-4-甲氧基-1,3,5(10)-雌三烯-17-酮
  参考文献：
  名称：

  Selective synthesis of 4-methoxyestrogen from 4-hydroxyestrogen

  摘要：

  The introduction of an oxygen atom into the C-6 position of 4-hydroxyestrogen allowed for the selective methylation of the two phenolic hydroxyl groups. When the B-oxo derivative of 4-hydroxyestrone was benzylated in ethanol, only the 3-monobenzyl ether was obtained without formation of the 4-monobenzyl ether. Moreover, the 6-carbonyl group was further reduced to methylene almost quantitatively in the reaction of 4-acetoxy-6-oxoestrone 3-benzyl ether derivative with sodium borohydride. Therefore, 4-methoxyestrogen was synthesized by essentially combining these two reactions. (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00236-1
• 作为产物：
  描述：

  3,4-dihydroxy-17,17-ethylenedioxy-1,3,5(10)-estratrien-6-one diacetate 在 吡啶 、 碳酸氢钠 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 13.0h， 生成 3-苄氧基-4-羟基-17,17-亚乙二氧基-1,3,5(10)-雌三烯-6-酮乙酸酯
  参考文献：
  名称：

  Selective synthesis of 4-methoxyestrogen from 4-hydroxyestrogen

  摘要：

  The introduction of an oxygen atom into the C-6 position of 4-hydroxyestrogen allowed for the selective methylation of the two phenolic hydroxyl groups. When the B-oxo derivative of 4-hydroxyestrone was benzylated in ethanol, only the 3-monobenzyl ether was obtained without formation of the 4-monobenzyl ether. Moreover, the 6-carbonyl group was further reduced to methylene almost quantitatively in the reaction of 4-acetoxy-6-oxoestrone 3-benzyl ether derivative with sodium borohydride. Therefore, 4-methoxyestrogen was synthesized by essentially combining these two reactions. (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00236-1