(1S,2S,3S)-3-chloro-1-(3'-hydroxy-4'-phenoxyphenyl)-3-phenylpropane-1,2-diol | 600173-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S,3S)-3-chloro-1-(3'-hydroxy-4'-phenoxyphenyl)-3-phenylpropane-1,2-diol
• CAS: 600173-46-4
• 化学式: C₂₁H₁₉ClO₄
• 分子量: 370.832
• InChiKey: OJTJNGLMOMYSSE-PCCBWWKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  69.92
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S)-3-chloro-1-(3'-hydroxy-4'-phenoxyphenyl)-3-phenylpropane-1,2-diol 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以97%的产率得到5-[(1'S)-1'-hydroxy-1'-((2S,3R)-3-phenyloxiran-2-yl)methyl]-2-phenoxyphenol
  参考文献：
  名称：

  A route to the structure proposed for puetuberosanol and approaches to the natural products marshrin and phebalosin

  摘要：

  Synthesis of the structure claimed for puetuberosanol 1 (using the Julia-Colonna oxidation in a key step) showed that the natural product was a different material. The isomeric epoxy alcohols 16-18 can be discounted from the alternatives. An analogue 19 of marshrin 2 was prepared but the synthesis of the natural product was thwarted by failure of a Julia-Colonna oxidation in the key step. The epoxy ketone 29 was prepared by Darzens condensation and was converted into (+/-)-phebalosin 3. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00624-0
• 作为产物：
  描述：

  (2E)-1-(3'-hydroxy-4'-phenoxyphenyl)-3-phenylprop-2-en-1-one 在 盐酸 、 zinc(II) tetrahydroborate 、 immobilized poly-L-leucine 、 双氧水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 尿素 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 (1S,2S,3S)-3-chloro-1-(3'-hydroxy-4'-phenoxyphenyl)-3-phenylpropane-1,2-diol
  参考文献：
  名称：

  A route to the structure proposed for puetuberosanol and approaches to the natural products marshrin and phebalosin

  摘要：

  Synthesis of the structure claimed for puetuberosanol 1 (using the Julia-Colonna oxidation in a key step) showed that the natural product was a different material. The isomeric epoxy alcohols 16-18 can be discounted from the alternatives. An analogue 19 of marshrin 2 was prepared but the synthesis of the natural product was thwarted by failure of a Julia-Colonna oxidation in the key step. The epoxy ketone 29 was prepared by Darzens condensation and was converted into (+/-)-phebalosin 3. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00624-0