(1S,1'RS,3aS,4RS,7aS)-1-tert-Butoxy-4-(1'-phenylthioethyl)-7a-methyl-3a,4,7,7a-tetrahydro-5(6)-indan-5-one | 138225-49-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1S,1'RS,3aS,4RS,7aS)-1-tert-Butoxy-4-(1'-phenylthioethyl)-7a-methyl-3a,4,7,7a-tetrahydro-5(6)-indan-5-one
• 英文别名: (1S,3aS,7aS)-7a-methyl-1-[(2-methylpropan-2-yl)oxy]-4-(1-phenylsulfanylethyl)-2,3,3a,4,6,7-hexahydro-1H-inden-5-one
• CAS: 138225-49-7；138225-50-0；138225-51-1；138225-52-2
• 化学式: C₂₂H₃₂O₂S
• 分子量: 360.561
• InChiKey: XHSGTWKPRAQPKW-UIJDMCKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,1'RS,3aS,4RS,7aS)-1-tert-Butoxy-4-(1'-phenylthioethyl)-7a-methyl-3a,4,7,7a-tetrahydro-5(6)-indan-5-one 在 镍 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以93%的产率得到(1S,3aS,4S,7aS)-(+)-1-tert-Butoxy-4-ethyl-7a-methyl-3a,4,7,7a-tetrahydro-5⁽⁶⁾-indan-5-one
  参考文献：
  名称：

  Zinc(II)-chloride induced thioalkylation of aluminium enolates; Enantioselective synthesis of estradiol-3-methyl-17-tert-butyl diether

  摘要：

  Zinc(II)-chloride induced thioalkylation of the aluminium enolate 6 generated by conjugate reduction of the enone 5 leads - directly or via its trimethylsilylenol ether 6 - to alkylated hydrindanones 10 which are important intermediates in the synthesis of 19-norsteroids such as the title compound estradiol-3-methyl-17-tert-butyl diether 12.

  DOI：

  10.1016/s0040-4020(01)88282-x
• 作为产物：
  描述：

  苯乙硫醚 在 zinc(II) chloride N-氯代丁二酰亚胺 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 (1S,1'RS,3aS,4RS,7aS)-1-tert-Butoxy-4-(1'-phenylthioethyl)-7a-methyl-3a,4,7,7a-tetrahydro-5(6)-indan-5-one
  参考文献：
  名称：

  Zinc(II)-chloride induced thioalkylation of aluminium enolates; Enantioselective synthesis of estradiol-3-methyl-17-tert-butyl diether

  摘要：

  Zinc(II)-chloride induced thioalkylation of the aluminium enolate 6 generated by conjugate reduction of the enone 5 leads - directly or via its trimethylsilylenol ether 6 - to alkylated hydrindanones 10 which are important intermediates in the synthesis of 19-norsteroids such as the title compound estradiol-3-methyl-17-tert-butyl diether 12.

  DOI：

  10.1016/s0040-4020(01)88282-x

文献信息

• Zinc(II)-chloride induced thioalkylation of aluminium enolates; Enantioselective synthesis of estradiol-3-methyl-17-tert-butyl diether
  作者：Ulrich Groth、Thomas Köhler、Thomas Taapken

  DOI：10.1016/s0040-4020(01)88282-x

  日期：1991.9

  Zinc(II)-chloride induced thioalkylation of the aluminium enolate 6 generated by conjugate reduction of the enone 5 leads - directly or via its trimethylsilylenol ether 6 - to alkylated hydrindanones 10 which are important intermediates in the synthesis of 19-norsteroids such as the title compound estradiol-3-methyl-17-tert-butyl diether 12.