2,2'-[2-(4-vinylphenyl)-1-(4-vinylbenzyl)ethylidene]bis[(4S)-4-tert-butyl-4,5-dihydro-2-oxazole] | 319489-95-7

• 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: 2,2'-[2-(4-vinylphenyl)-1-(4-vinylbenzyl)ethylidene]bis[(4S)-4-tert-butyl-4,5-dihydro-2-oxazole]
• 英文别名: 2,2'-(1,3-di(p-vinylphenyl)isopropylidene)bis[(4S)-4-tert-butyl-2-oxazoline]；(4S)-4-tert-butyl-2-[2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]-1,3-bis(4-ethenylphenyl)propan-2-yl]-4,5-dihydro-1,3-oxazole
• CAS: 319489-95-7
• 化学式: C₃₃H₄₂N₂O₂
• 分子量: 498.709
• InChiKey: VGUGBXBLAQCUKH-VSGBNLITSA-N

物化性质

• 沸点：
  606.4±55.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯甲基苯乙烯 、 2,2′-亚甲基双[(4,s)-4-叔丁基-2-噁唑啉] 在 甲基锂 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 2,2'-[2-(4-vinylphenyl)-1-(4-vinylbenzyl)ethylidene]bis[(4S)-4-tert-butyl-4,5-dihydro-2-oxazole]
  参考文献：
  名称：

  聚合物负载的双（恶唑啉）-铜配合物在环丙烷化反应中的催化剂

  摘要：

  通过用可聚合基团对中心亚甲基桥进行官能化以及随后的聚合，可以轻松地固定双（恶唑啉）。聚合物被转化为铜催化剂，该催化剂对苯乙烯与重氮乙酸乙酯的环丙烷化反应具有活性。结果与使用相似的均相系统获得的结果相似甚至更好，并且催化剂可以轻松回收和再利用。在亚甲基桥中的取代导致对映选择性的轻微降低和意外的顺式偏好。

  DOI：

  10.1021/ol0066633

文献信息

• Polymer immobilization of bis(oxazoline) ligands using dendrimers as cross-linkers
  作者：Enrique Dı́ez-Barra、José M Fraile、José I Garcı́a、Eduardo Garcı́a-Verdugo、Clara I Herrerı́as、Santiago V Luis、José A Mayoral、Prado Sánchez-Verdú、Juan Tolosa

  DOI：10.1016/s0957-4166(03)00074-0

  日期：2003.4

  Homopolymers of bis(oxazoline) ligands can be used to prepare efficient catalysts for cyclopropanation reactions. However, the low accessibility to most bis(oxazoline) moieties leads to a low copper loading. As a consequence, the transmission of chiral information from the complexed polymer is not very efficient and only a few chiral cyclopropane molecules are obtained from each molecule of chiral ligand. The use of suitable dendrimers as cross-linkers in the polymerization process allows better copper functionalization. As a consequence the productivity of chiral cyclopropanes per molecule of chiral ligand greatly increases, which improves the ligand economy and the chirality transfer. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Bis(oxazoline)copper Complexes Covalently Bonded to Insoluble Support as Catalysts in Cyclopropanation Reactions
  作者：M. Isabel Burguete、José M. Fraile、José I. García、Eduardo García-Verdugo、Clara I. Herrerías、Santiago V. Luis、José A. Mayoral

  DOI：10.1021/jo0159338

  日期：2001.12.1

  Chiral bis(oxazolines) are readily dialkylated in the methylene bridge, opening the way to immobilization at that position, keeping the C-2 symmetry of the chiral ligand. Bis(oxazolines) functionalized with two allyl or vinylbenzyl groups are easily grafted onto mercaptopropylsilica. Another approach to immobilization is the polymerization of the ligands bearing vinylbenzyl groups to yield insoluble polymers. The Cu(OTf)(2) complexes of the immobilized ligands promote the enantioselective cyclopropanation reaction between styrene and ethyl diazoacetate. The results depend on the nature of the support and the method of immobilization. With regard to the type of solid, the best results, which are similar to or even better than those obtained with the corresponding dibenzylated homogeneous catalysts, are obtained with homopolymers. With regard to the bis(oxazoline), that bearing indan groups leads to good results both onto silica and polymers, whereas with the ligand bearing tert-butyl groups good enantioselectivities are only obtained with homopolymeric catalysts. Some of the heterogeneous catalysts can be easily recovered and reused, as much as five times, with the same yield and stereoselectivities.