Thioacetic acid S-((1R,2S)-1-phenyl-2-piperidin-1-yl-propyl) ester | 166031-44-3

• 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: Thioacetic acid S-((1R,2S)-1-phenyl-2-piperidin-1-yl-propyl) ester
• 英文别名: S-[(1R,2S)-1-phenyl-2-piperidin-1-ylpropyl] ethanethioate
• CAS: 166031-44-3
• 化学式: C₁₆H₂₃NOS
• 分子量: 277.431
• InChiKey: UBXZRJNMGWYLMD-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Thioacetic acid S-((1R,2S)-1-phenyl-2-piperidin-1-yl-propyl) ester 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 以97%的产率得到(1R,2S)-(-)-1-phenyl-2-piperidinopropane-1-thiol
  参考文献：
  名称：

  Enantioselective addition of diethylzinc to α-branched aldehydes

  摘要：

  在催化量的(1R,2S)-(–)-1-苯基-2-哌啶丙烷-1-硫醇1存在下，二乙基锌与α-支链醛的反应几乎以100%的外消旋过剩量提供了相应的二级醇。

  DOI：

  10.1039/c39940002009
• 作为产物：
  描述：

  去甲麻黄碱 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 Thioacetic acid S-((1R,2S)-1-phenyl-2-piperidin-1-yl-propyl) ester
  参考文献：
  名称：

  Enantioselective addition of diethylzinc to α-branched aldehydes

  摘要：

  在催化量的(1R,2S)-(–)-1-苯基-2-哌啶丙烷-1-硫醇1存在下，二乙基锌与α-支链醛的反应几乎以100%的外消旋过剩量提供了相应的二级醇。

  DOI：

  10.1039/c39940002009
• 作为试剂：
  描述：

  邻甲氧基苯甲醛 、 苯硼酸 在 diethylzinc 、 Thioacetic acid S-((1R,2S)-1-phenyl-2-piperidin-1-yl-propyl) ester 作用下， 以 甲苯 为溶剂， 反应 13.33h， 以93%的产率得到(R)-(2-methoxyphenyl)phenylmethanol
  参考文献：
  名称：

  Highly Enantioselective Aryl Transfer to Aldehydes:  A Remarkable Effect of Sulfur Substitution in Amino Thioacetate Ligands

  摘要：

  Chiral amino thioacetate ligands were prepared from the corresponding amino alcohols and used as catalysts for enantioselective aryl transfer reaction. The amino thioacetates were remarkably superior to the corresponding amino alcohols, Low catalyst loadings of only 1-2.5 mol % were sufficient to achieve excellent enantioselectivity as well as high conversion in short reaction time. The results reveal that the thioacetoxy moiety of the amino thioacetates has a surprisingly beneficial effect in enhancing the asymmetric induction.

  DOI：

  10.1021/ol8001249

文献信息

• Enantioselective addition of diethylzinc to α-branched aldehydes
  作者：Jahyo Kang、Jun Won Lee、Joo In Kim

  DOI：10.1039/c39940002009

  日期：——

  Reaction of diethylzinc with α-branched aldehydes in the presence of a catalytic amount of (1R,2S)-(–)-1-phenyl-2-piperidinopropane-1-thiol 1 provided the corresponding secondary alcohols in almost 100% enantiomeric excess.

  在催化量的(1R,2S)-(–)-1-苯基-2-哌啶丙烷-1-硫醇1存在下，二乙基锌与α-支链醛的反应几乎以100%的外消旋过剩量提供了相应的二级醇。
• Highly Enantioselective Aryl Transfer to Aldehydes:  A Remarkable Effect of Sulfur Substitution in Amino Thioacetate Ligands
  作者：Myung-Jong Jin、Shaheen M. Sarkar、Dong-Hwan Lee、Huili Qiu

  DOI：10.1021/ol8001249

  日期：2008.3.1

  Chiral amino thioacetate ligands were prepared from the corresponding amino alcohols and used as catalysts for enantioselective aryl transfer reaction. The amino thioacetates were remarkably superior to the corresponding amino alcohols, Low catalyst loadings of only 1-2.5 mol % were sufficient to achieve excellent enantioselectivity as well as high conversion in short reaction time. The results reveal that the thioacetoxy moiety of the amino thioacetates has a surprisingly beneficial effect in enhancing the asymmetric induction.