(+)-(R,E)-1,3-diphenyl-3-(tert-butylsulfonyl)prop-1-ene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (+)-(R,E)-1,3-diphenyl-3-(tert-butylsulfonyl)prop-1-ene
• 英文别名: [(E,3R)-3-tert-butylsulfonyl-3-phenylprop-1-enyl]benzene
• 化学式: C₁₉H₂₂O₂S
• 分子量: 314.448
• InChiKey: AJFOQUAVOFAHEH-LGHUBQEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl (E)-1,3-diphenyl-2-propen-1-yl carbonate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 Oxone 、 chiral oxazole substituted triphenylphosphine 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.5h， 生成 (+)-(R,E)-1,3-diphenyl-3-(tert-butylsulfonyl)prop-1-ene
  参考文献：
  名称：

  Pd-catalyzed asymmetric synthesis of allylic tert-butyl sulfones and sulfides: Kinetic resolution of the allylic substrate by a chiral Pd-complex

  摘要：

  The acyclic and cyclic allylic tert-butyl sulfones 3, ent-3, 11a, 11b and 15a-c of 89-98% ee were synthesized in 40-92% yield by a Pd-catalyzed reaction of the respective allylic acetates and carbonates rac-1a, rac-1b, rac-10a, rac-10b and rac-14a-c with LiO(2)St-Bu in the presence of the chiral ligands 2a, ent-2b and 12. Formation of the n-butyl sulfones 13a and 13b of 95% ee was observed. Reactions of rac-1a and 1b/ent-1b with LiO(2)St-Bu in the presence of 2a and ent-2b, respectively, in THF under heterogeneous conditions were accompanied by a kinetic resolution of the allylic substrates. The faster reacting allylic substrate and the preferentially formed sulfone had the same absolute configuration. The allylic tert-butyl sulfide 17 of 92% ee was obtained in 63% yield by the Pd-catalyzed reaction of rac-1b with Me(3)SiSt-Bu in the presence of ent-2b. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00601-0

文献信息

• Pd-catalyzed asymmetric synthesis of allylic tert-butyl sulfones and sulfides: Kinetic resolution of the allylic substrate by a chiral Pd-complex
  作者：Hans-Joachim Gais、Holger Eichelmann、Nicole Spalthoff、Frank Gerhards、Michael Frank、Gerhard Raabe

  DOI：10.1016/s0957-4166(97)00601-0

  日期：1998.1

  The acyclic and cyclic allylic tert-butyl sulfones 3, ent-3, 11a, 11b and 15a-c of 89-98% ee were synthesized in 40-92% yield by a Pd-catalyzed reaction of the respective allylic acetates and carbonates rac-1a, rac-1b, rac-10a, rac-10b and rac-14a-c with LiO(2)St-Bu in the presence of the chiral ligands 2a, ent-2b and 12. Formation of the n-butyl sulfones 13a and 13b of 95% ee was observed. Reactions of rac-1a and 1b/ent-1b with LiO(2)St-Bu in the presence of 2a and ent-2b, respectively, in THF under heterogeneous conditions were accompanied by a kinetic resolution of the allylic substrates. The faster reacting allylic substrate and the preferentially formed sulfone had the same absolute configuration. The allylic tert-butyl sulfide 17 of 92% ee was obtained in 63% yield by the Pd-catalyzed reaction of rac-1b with Me(3)SiSt-Bu in the presence of ent-2b. (C) 1998 Elsevier Science Ltd. All rights reserved.