2,2'-bis[(S)-4-isopropyloxazolin-2-yl]diphenylsulfide | 464181-03-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,2'-bis[(S)-4-isopropyloxazolin-2-yl]diphenylsulfide
• 英文别名: (4S)-4-propan-2-yl-2-[2-[2-[(4S)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]sulfanylphenyl]-4,5-dihydro-1,3-oxazole
• CAS: 464181-03-1
• 化学式: C₂₄H₂₈N₂O₂S
• 分子量: 408.565
• InChiKey: CFQZOZRLKCTXOB-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  68.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-缬氨醇 在 甲基磺酰氯 、 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 甲醇 、 水 为溶剂， 反应 4.0h， 以73%的产率得到2,2'-bis[(S)-4-isopropyloxazolin-2-yl]diphenylsulfide
  参考文献：
  名称：

  Rational tuning of the rigidity of a ligand scaffold: synthesis of diphenylsulfide-linked bis(oxazoline) ligands and their application in asymmetric allylic alkylation

  摘要：

  The scaffold rigidity of bis(oxazoline) ligands was rationally tuned on the basis of literature information. Diphenylsulfide-linked bis(oxazoline) ligands with a flexible scaffold were efficiently synthesized to test our hypothesis. The improved enantioselectivity in palladium-catalyzed asymmetric allylic alkylation reaction was achieved as we expected. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.015
• 作为试剂：
  描述：

  (±)-反式-1,3-二苯基烯丙基乙酸酯 、 丙二酸二乙酯 在 bis(η3-allyl-μ-chloropalladium(II)) 、 2,2'-bis[(S)-4-isopropyloxazolin-2-yl]diphenylsulfide 、 potassium acetate 作用下， 以 甲苯 为溶剂， 反应 24.67h， 生成 diethyl 2-[(1S,2E)-1,3-diphenyl-2-propenyl]malonate 、 2-[(1R,2E)-1,3-二苯基-2-丙烯-1-基]丙二酸二乙酯
  参考文献：
  名称：

  Rational tuning of the rigidity of a ligand scaffold: synthesis of diphenylsulfide-linked bis(oxazoline) ligands and their application in asymmetric allylic alkylation

  摘要：

  The scaffold rigidity of bis(oxazoline) ligands was rationally tuned on the basis of literature information. Diphenylsulfide-linked bis(oxazoline) ligands with a flexible scaffold were efficiently synthesized to test our hypothesis. The improved enantioselectivity in palladium-catalyzed asymmetric allylic alkylation reaction was achieved as we expected. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.015

文献信息

• Rational tuning of the rigidity of a ligand scaffold: synthesis of diphenylsulfide-linked bis(oxazoline) ligands and their application in asymmetric allylic alkylation
  作者：Xian Du、Han Liu、Da-Ming Du

  DOI：10.1016/j.tetasy.2010.01.015

  日期：2010.2

  The scaffold rigidity of bis(oxazoline) ligands was rationally tuned on the basis of literature information. Diphenylsulfide-linked bis(oxazoline) ligands with a flexible scaffold were efficiently synthesized to test our hypothesis. The improved enantioselectivity in palladium-catalyzed asymmetric allylic alkylation reaction was achieved as we expected. (C) 2010 Elsevier Ltd. All rights reserved.