2-(3'-carboxypropyl)estrone lactone | 474459-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(3'-carboxypropyl)estrone lactone
• 英文别名: (2S,5S,9S,10R)-5-methyl-16-oxapentacyclo[11.9.0.02,10.05,9.015,21]docosa-1(13),14,21-triene-6,17-dione
• CAS: 474459-36-4
• 化学式: C₂₂H₂₆O₃
• 分子量: 338.447
• InChiKey: MFMGBPPNPOBZBY-UTAOTPEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3'-carboxypropyl)estrone lactone 、 2-(1-chloroethyl)-4,4-dimethyl-2-oxazoline 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以60%的产率得到(2S,3'R,5S,6S,9S,10R)-3'-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-3',5-dimethylspiro[16-oxapentacyclo[11.9.0.02,10.05,9.015,21]docosa-1(13),14,21-triene-6,2'-oxirane]-17-one
  参考文献：
  名称：

  Chemoselective construction of novel steroid derivatives

  摘要：

  alpha-Halo-alpha-heteroarylalkyllithiums, generated by deprotonation of the corresponding halides, when added promptly to steroids with C=O or C=NR groups, lead to epoxides and aziridines. The reactions are regio- and stereoselective; in fact, in the presence of more than one C=O group, the oxido or aziridino functions are formed uniquely at the C=O of C-17 (or C-20 depending on its position in the starting molecule), and the C-20(R) stereoisomer is often the only product isolated. Protection of the hydroxyl group present on several considered steroids was required, and it was accomplished through derivatization in acetyl, ether, or lactone. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00032-6
• 作为产物：
  描述：

  雌酚酮 在 sodium hydroxide 、 N,N-二乙基苯胺 作用下， 以 丙酮 为溶剂， 60.0~220.0 ℃ 、4.14 MPa 条件下， 反应 27.0h， 生成 2-(3'-carboxypropyl)estrone lactone
  参考文献：
  名称：

  Chemoselective construction of novel steroid derivatives

  摘要：

  alpha-Halo-alpha-heteroarylalkyllithiums, generated by deprotonation of the corresponding halides, when added promptly to steroids with C=O or C=NR groups, lead to epoxides and aziridines. The reactions are regio- and stereoselective; in fact, in the presence of more than one C=O group, the oxido or aziridino functions are formed uniquely at the C=O of C-17 (or C-20 depending on its position in the starting molecule), and the C-20(R) stereoisomer is often the only product isolated. Protection of the hydroxyl group present on several considered steroids was required, and it was accomplished through derivatization in acetyl, ether, or lactone. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00032-6