(1R^*,2S^*,3S^*)-3-(Dibenzylamino)-1,4-diphenyl-1-(phenylthio)-2-butanol | 145127-98-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (1R^*,2S^*,3S^*)-3-(Dibenzylamino)-1,4-diphenyl-1-(phenylthio)-2-butanol
• 英文别名: (1R,2S,3S)-3-(dibenzylamino)-1,4-diphenyl-1-phenylsulfanylbutan-2-ol
• CAS: 145127-98-6；145167-85-7；145167-96-0；145167-97-1
• 化学式: C₃₆H₃₅NOS
• 分子量: 529.746
• InChiKey: UNIMNBZFPDSYJE-QGBCWPEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  48.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (rac)-2-(dibenzylamino)-3-phenylpropionaldehyde 、 phenyl α-tributylstannylbenzyl sulfide 在 正丁基锂 、 四甲基乙二胺 作用下， 以 正己烷 为溶剂， 反应 1.17h， 生成 (1S,2S,3S)-3-(Dibenzylamino)-1,4-diphenyl-1-(phenylthio)-2-butanol 、 (1R^*,2S^*,3S^*)-3-(Dibenzylamino)-1,4-diphenyl-1-(phenylthio)-2-butanol
  参考文献：
  名称：

  Enantioselective Reactions of Configurationally Unstableα-Thiobenzyllithium Compounds

  摘要：

  Too unstable for asymmetric deprotonation, alpha-sulfenyl carbanions can undergo asymmetric substitution reactions with high stereoselectivity [Eq. (1)]. The key to the asymmetric induction is the dynamic kinetic resolution of the complex formed between the organolithium compound and a chiral ligand, the most effective of which were bisoxazoline derivatives.

  DOI：

  10.1002/(sici)1521-3773(20000117)39:2<353::aid-anie353>3.0.co;2-1

文献信息

• Hoffmann, Reinhard W.; Ruehl, Thomas; Harbach, Juergen, Liebigs Annalen der Chemie, 1992, # 7, p. 725 - 730
  作者：Hoffmann, Reinhard W.、Ruehl, Thomas、Harbach, Juergen

  DOI：——

  日期：——
• Enantioselective Reactions of Configurationally Unstableα-Thiobenzyllithium Compounds
  作者：Shuichi Nakamura、Ryo Nakagawa、Yoshihiko Watanabe、Takeshi Toru

  DOI：10.1002/(sici)1521-3773(20000117)39:2<353::aid-anie353>3.0.co;2-1

  日期：2000.1.17

  Too unstable for asymmetric deprotonation, alpha-sulfenyl carbanions can undergo asymmetric substitution reactions with high stereoselectivity [Eq. (1)]. The key to the asymmetric induction is the dynamic kinetic resolution of the complex formed between the organolithium compound and a chiral ligand, the most effective of which were bisoxazoline derivatives.