2,2'-[2-(4-vinylphenyl)-1-(4-vinylbenzyl)ethylidene]bis[(4S)-4-phenyl-4,5-dihydro-2-oxazole] | 319489-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2'-[2-(4-vinylphenyl)-1-(4-vinylbenzyl)ethylidene]bis[(4S)-4-phenyl-4,5-dihydro-2-oxazole]
• 英文别名: 2,2'-(1,3-di(p-vinylphenyl)isopropylidene)bis[(4S)-4-phenyl-2-oxazoline]；(4S)-2-[1,3-bis(4-ethenylphenyl)-2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propan-2-yl]-4-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 319489-93-5
• 化学式: C₃₇H₃₄N₂O₂
• 分子量: 538.689
• InChiKey: GYNQLDNQTKKXBY-KKLWWLSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  L-苯甘氨酸 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 145.0h， 生成 2,2'-[2-(4-vinylphenyl)-1-(4-vinylbenzyl)ethylidene]bis[(4S)-4-phenyl-4,5-dihydro-2-oxazole]
  参考文献：
  名称：

  连续流动法处理铜介导的α-重氮酮异质对映选择性布氏反应

  摘要：

  α-重氮酮的对映选择性分子内布氏反应可以分批使用多相铜-双（恶唑啉）催化剂，也可以使用连续流工艺以高达83％ee的方式进行。催化剂可以重复使用多达7次，而不会失去活性。对于α-重氮酮3和4，固定化催化剂在流动中获得的对映异构体可与标准均相催化过程相媲美。

  DOI：

  10.1021/acs.joc.8b00147

文献信息

• Polymer-Supported Bis(oxazoline)−Copper Complexes as Catalysts in Cyclopropanation Reactions
  作者：M. Isabel Burguete、José M. Fraile、José I. García、Eduardo García-Verdugo、Santiago V. Luis、José A. Mayoral

  DOI：10.1021/ol0066633

  日期：2000.11.1

  Bis(oxazolines) are easily immobilized by functionalization of the central methylene bridge with polymerizable groups and subsequent polymerization. Polymers are transformed into copper catalysts active in the cyclopropanation of styrene with ethyl diazoacetate. The results are similar or even better than those obtained with the similar homogeneous systems, and the catalysts can be easily recovered

  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。
• 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.
• Improvement of ligand economy controlled by polymer morphology: The case of polymer-Supported bis(oxazoline) catalysts
  作者：M.I. Burguete、E. Dı́ez-Barra、J.M. Fraile、J.I. Garcı́a、E. Garcı́a-Verdugo、R. González、C.I. Herrerı́as、S.V. Luis、J.A. Mayoral

  DOI：10.1016/s0960-894x(02)00259-7

  日期：2002.7

  A functionalized chiral bis(oxazoline) is used as a chiral monomer in polymerization reactions leading to homo- and copolymers of different morphology. Polymers with a high content of chiral monomer lead to enantioselectivities that are higher than those obtained with the soluble ligand, but the chiral ligand is not used in an optimal way. A hyperbranched polymer, obtained by using a hexavinyldendrimer as the cross-linker, leads to the same enantioselectivities with a more efficient use of the chiral ligand. (C) 2002 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.