(S)-(1R,2S)-1,2-diphenyl-2-(piperidin-1-yl)ethyl ethanethioate | 160011-79-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (S)-(1R,2S)-1,2-diphenyl-2-(piperidin-1-yl)ethyl ethanethioate
• 英文别名: S-[(1R,2S)-1,2-diphenyl-2-piperidin-1-ylethyl] ethanethioate
• CAS: 160011-79-0
• 化学式: C₂₁H₂₅NOS
• 分子量: 339.502
• InChiKey: VISFTSZWCRQUGC-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (S)-(1R,2S)-1,2-diphenyl-2-(piperidin-1-yl)ethyl ethanethioate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (1R,2S)-1,2-diphenyl-2-(piperidin-1-yl)ethanethiol
  参考文献：
  名称：

  New β-amino thiols as efficient catalysts for highly enantioselective alkenylzinc addition to aldehydes

  摘要：

  A series of new optically active beta-amino thiols and thiolacetates prepared from the simple natural amino acid, (S)-(-)-valine, were found to be effective catalysts for the enantioselective addition of alkenylzinc to alclehydes and thereby providing an efficient route for chiral (E)-allylic alcohols with ees of up to >99% in the presence of 7a (1 mol %). (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.11.093
• 作为产物：
  描述：

  (1R,2S)-2-氨基-1,2-二苯基乙醇 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 27.0h， 生成 (S)-(1R,2S)-1,2-diphenyl-2-(piperidin-1-yl)ethyl ethanethioate
  参考文献：
  名称：

  New β-amino thiols as efficient catalysts for highly enantioselective alkenylzinc addition to aldehydes

  摘要：

  A series of new optically active beta-amino thiols and thiolacetates prepared from the simple natural amino acid, (S)-(-)-valine, were found to be effective catalysts for the enantioselective addition of alkenylzinc to alclehydes and thereby providing an efficient route for chiral (E)-allylic alcohols with ees of up to >99% in the presence of 7a (1 mol %). (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.11.093
• 作为试剂：
  描述：

  4-甲苯硼酸 、 苯甲醛 在 diethylzinc 、 (S)-(1R,2S)-1,2-diphenyl-2-(piperidin-1-yl)ethyl ethanethioate 作用下， 以 甲苯 为溶剂， 反应 13.33h， 以90%的产率得到(R)-苯基(4-甲苯基)甲醇
  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

• US7335781B2
  申请人：——

  公开号：US7335781B2

  公开（公告）日：2008-02-26