(+)-7α-(5-bromopentyl)-17-hydroxy-3-oxo-17α-pregn-4-ene-21-carboxylic acid γ-lactone | 1430413-05-0

• 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: (+)-7α-(5-bromopentyl)-17-hydroxy-3-oxo-17α-pregn-4-ene-21-carboxylic acid γ-lactone
• 英文别名: (+)-7α-(5-bromopentyl)-17α-hydroxy-3-oxo-pregn-4-ene-21-carboxylic acid γ-lactone；(+)-α-(5-bromopentyl)-17α-hydroxy-3-oxo-pregn-4-ene-21-carboxylic acid γ-lactone；(7R,8R,9S,10R,13S,14S,17R)-7-(5-bromopentyl)-10,13-dimethylspiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione
• CAS: 1430413-05-0
• 化学式: C₂₇H₃₉BrO₃
• 分子量: 491.509
• InChiKey: FZPANCCUKYJZOD-GBACRHRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  坎利酮 、 5-溴-1-戊烯 在 Schwartz's reagent 、 (S)-1,1'-Binaphthyl-2,2'-diyl bis((1S)-1-phenylethyl)phosphoramidite copper(I) triflate 、 三甲基氯硅烷 作用下， 以 二氯甲烷 、 乙醚 为溶剂， 反应 15.42h， 以33%的产率得到(+)-7α-(5-bromopentyl)-17-hydroxy-3-oxo-17α-pregn-4-ene-21-carboxylic acid γ-lactone
  参考文献：
  名称：

  Hydrometallation-asymmetric conjugate addition: application to complex molecule synthesis

  摘要：

  铜催化允许在烯烃中原位生成的烷基锆物种进行共轭加成反应。采用氢金属化-催化不对称1,4-加成，从商业可得的材料中一步合成天然产物的任一对映体。应用于含有交叉共轭二烯酮或1,6-受体的类固醇的氢金属化-加成序列能够得到高功能化的产物。

  DOI：

  10.1039/c2cc37155c

文献信息

• ASYMMETRIC SYNTHESIS OF ORGANIC COMPOUNDS
  申请人：Isis Innovation Limited

  公开号：US20140303385A1

  公开（公告）日：2014-10-09

  The present invention provides processes for the production of chiral compounds in a stereoisomeric excess. The present processes involve reacting a hydrometallated alkene compound with a compound comprising a conjugated-bond system under conditions such that the compounds undergo an asymmetric 1,4- or 1,6-conjugate addition reaction, generating a chiral compound in a stereoisomeric excess. The reaction is performed in the presence of a metal catalyst, which catalyst preferably comprises a non-racemic chiral ligand.

  本发明提供了用于在立体异构体过量中生产手性化合物的工艺。目前的工艺涉及将氢金属化的烯烃化合物与包含共轭键系统的化合物在条件下反应，使得这些化合物经历不对称的1,4-或1,6-共轭加成反应，生成手性化合物的立体异构体过量。反应在金属催化剂存在下进行，该催化剂最好包括非外消旋手性配体。
• [EN] ASYMMETRIC SYNTHESIS OF ORGANIC COMPOUNDS<br/>[FR] SYNTHÈSE ASYMÉTRIQUE DE COMPOSÉS ORGANIQUES
  申请人：ISIS INNOVATION

  公开号：WO2013054131A1

  公开（公告）日：2013-04-18

  The present invention provides processes for the production of chiral compounds in a stereoisomeric excess. The present processes involve reacting a hydrometallated alkene compound with a compound comprising a conjugated -bond system under conditions such that the compounds undergo an asymmetric 1,4- or 1,6-conjugate addition reaction, generating a chiral compound in a stereoisomeric excess. The reaction is performed in the presence of a metal catalyst, which catalyst preferably comprises a non-racemic chiral ligand.

  本发明提供了用于在立体异构物过量中生产手性化合物的过程。目前的过程涉及将一个氢金属化的烯烃化合物与包含一个共轭-键系统的化合物在条件下反应，使得这些化合物经历不对称的1,4-或1,6-共轭加成反应，生成手性化合物的立体异构物过量。反应在金属催化剂存在下进行，该催化剂最好包括一个非外消旋手性配体。
• US9090545B2
  申请人：——

  公开号：US9090545B2

  公开（公告）日：2015-07-28
• Hydrometallation-asymmetric conjugate addition: application to complex molecule synthesis
  作者：Rebecca M. Maksymowicz、Philippe M. C. Roth、Amber L. Thompson、Stephen P. Fletcher

  DOI：10.1039/c2cc37155c

  日期：——

  Copper catalysis allows alkyl zirconium species, generated in situ from alkenes, to undergo conjugate addition reactions. A hydrometallation-catalytic asymmetric 1,4-addition was used to synthesize either enantiomer of a natural product in one step from commercially available materials. Hydrometallation-addition sequences applied to steroids containing a cross-conjugated dienone or 1,6-acceptor give highly functionalized products.

  铜催化允许在烯烃中原位生成的烷基锆物种进行共轭加成反应。采用氢金属化-催化不对称1,4-加成，从商业可得的材料中一步合成天然产物的任一对映体。应用于含有交叉共轭二烯酮或1,6-受体的类固醇的氢金属化-加成序列能够得到高功能化的产物。