4-(3'-carboxypropyl)estrone lactone | 222834-74-4

• 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
• 英文名称: 4-(3'-carboxypropyl)estrone lactone
• 英文别名: (2S,5S,9S,10R)-5-methyl-19-oxapentacyclo[11.9.0.02,10.05,9.014,20]docosa-1(13),14(20),21-triene-6,18-dione
• CAS: 222834-74-4
• 化学式: C₂₂H₂₆O₃
• 分子量: 338.447
• InChiKey: PGBIOJIYXGLUJS-LVOOAJGHSA-N

物化性质

• 沸点：
  507.483±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.184±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

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-(1-chloroethyl)-4,4-dimethyl-2-oxazoline 、 4-(3'-carboxypropyl)estrone lactone 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68%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[19-oxapentacyclo[11.9.0.02,10.05,9.014,20]docosa-1(13),14(20),21-triene-6,2'-oxirane]-18-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：

  3-allyloxy estrone 在 palladium diacetate 、 氢气 、 1,4-双(二苯基膦)丁烷 、 N,N-二乙基苯胺 作用下， 以 甲苯 为溶剂， 110.0~120.0 ℃ 、4.14 MPa 条件下， 反应 48.0h， 生成 4-(3'-carboxypropyl)estrone lactone
  参考文献：
  名称：

  钯（II）催化类固醇的区域选择性内酯化。新型雌酮衍生物的化学选择性构建

  摘要：

  乙酸钯和1,4-双（二苯基膦基）丁烷（dppb）催化4-烯丙基类固醇的区域选择性环羰基化，形成仅7元环内酯，产率极高（96–98％）。通过将甾族化合物的环戊酮环上的羰基与2-苯并噻唑基氯甲基锂1或4，4-二甲基-2-恶唑啉基氯代烷基22和3偶联，可以在甾族化合物的侧链上立体选择性地加成环氧化物。

  DOI：

  10.1016/s0040-4039(99)00094-5

文献信息

• Chemoselective construction of novel steroid derivatives
  作者：Luigino Troisi、Saverio Florio、Catia Granito

  DOI：10.1016/s0039-128x(02)00032-6

  日期：2002.7

  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.
• Palladium (II) catalyzed regioselective lactonization of steroids. Chemoselective construction of novel estrone derivatives
  作者：L. Troisi、G. Vasapollo、B. El Ali、G. Mele、S. Florio、V. Capriati

  DOI：10.1016/s0040-4039(99)00094-5

  日期：1999.2

  Palladium acetate and 1,4-bis(diphenylphosphino)butane (dppb) catalyze regioselective cyclocarbonylation of 4-allylsteroids forming exclusively 7-membered ring lactones with excellent yields (96–98 %). The stereoselective addition of an epoxide ring on the side-chain of steroids is realized by coupling the carbonyl group of the cyclopentanone ring of the steroid with 2-benzothiazolylchloromethyllithium

  乙酸钯和1,4-双（二苯基膦基）丁烷（dppb）催化4-烯丙基类固醇的区域选择性环羰基化，形成仅7元环内酯，产率极高（96–98％）。通过将甾族化合物的环戊酮环上的羰基与2-苯并噻唑基氯甲基锂1或4，4-二甲基-2-恶唑啉基氯代烷基22和3偶联，可以在甾族化合物的侧链上立体选择性地加成环氧化物。