3-苄氧基-4-羟基-17,17-亚乙二氧基-1,3,5(10)-雌三烯-6-酮 | 360771-93-3

• 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
• 英文名称: 3-benzyloxy-4-hydroxy-17,17-ethylenedioxy-1,3,5(10)-estratrien-6-one
• 英文别名: (8'R,9'S,13'S,14'S)-4'-hydroxy-13'-methyl-3'-phenylmethoxyspiro[1,3-dioxolane-2,17'-7,8,9,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene]-6'-one
• CAS: 360771-93-3
• 化学式: C₂₇H₃₀O₅
• 分子量: 434.532
• InChiKey: NMWOMPZZNCLIBW-KKSJDHSTSA-N

物化性质

• 沸点：
  602.0±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

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 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 18.5h， 生成 4-甲氧基雌酚酮
  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 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
  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

文献信息

• Selective synthesis of 4-methoxyestrogen from 4-hydroxyestrogen
  作者：Masanori Teranishi、Mayumi Kashihara、Youichi Fujii

  DOI：10.1016/s0039-128x(00)00236-1

  日期：2001.8

  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.