diethyl 2-[(1S,2E)-1,3-bis(naphth-1-yl)prop-2-en-1-yl]malonate | 1224301-60-3

• 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: diethyl 2-[(1S,2E)-1,3-bis(naphth-1-yl)prop-2-en-1-yl]malonate
• 英文别名: (S)-diethyl 2-[(E)-1,3-bis(1-naphthyl)prop-2-en-1-yl]malonate
• CAS: 1224301-60-3
• 化学式: C₃₀H₂₈O₄
• 分子量: 452.55
• InChiKey: REBZPSUYDGLONF-CTNGAPNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.53
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  丙二酸二乙酯 、 (E)-1,3-di(naphthalen-1-yl)allyl acetate 在 bis(η3-allyl-μ-chloropalladium(II)) 、 2,2'-bis[(S)-4-tert-butyloxazolin-2-yl]diphenylsulfide 、 potassium acetate 作用下， 以 甲苯 为溶剂， 反应 36.67h， 以98%的产率得到diethyl 2-[(1S,2E)-1,3-bis(naphth-1-yl)prop-2-en-1-yl]malonate
  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

• Synthesis and Application of Diphenyl Sulfide Linked Bis(imidazoline) Ligands: Dramatic Electronic Effect of Ligands on Catalytic Behavior
  作者：Xian Du、Han Liu、Da-Ming Du

  DOI：10.1002/ejoc.201001347

  日期：2011.2

  Diphenyl sulfide linked bis(imidazoline) ligands with electron-withdrawing N-Ts substitution and electron-donating N-alkyl or N-H substitutions were synthesized through different routes. The electronic effects of the ligands were tuned rationally, and dramatic variation in their catalytic behavior was observed. N-Alkyl and N-H ligands demonstrated much higher catalytic activity and improved enantioselectivity

  通过不同的途径合成了具有吸电子N-Ts取代和供电子N-烷基或NH取代的二苯硫醚连接的双(咪唑啉)配体。配体的电子效应被合理调整，并观察到其催化行为的显着变化。N-烷基和NH配体在Pd催化的不对称烯丙基烷基化反应中表现出比N-Ts配体更高的催化活性和更高的对映选择性。