Toluene-4-sulfonic acid 4-(4-vinyl-benzyloxy)-butyl ester | 364356-60-5

• 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: Toluene-4-sulfonic acid 4-(4-vinyl-benzyloxy)-butyl ester
• 英文别名: 4-[(4-Ethenylphenyl)methoxy]butyl 4-methylbenzenesulfonate；4-[(4-ethenylphenyl)methoxy]butyl 4-methylbenzenesulfonate
• CAS: 364356-60-5
• 化学式: C₂₀H₂₄O₄S
• 分子量: 360.474
• InChiKey: KYRQRZBRHRHOIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid 4-(4-vinyl-benzyloxy)-butyl ester 在 4-二甲氨基吡啶 氢氧化钾 、 草酰氯 、 sodium hydride 、 三乙胺 、 对苯二酚 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 81.0h， 生成 (4S)-2-[6-[(4-ethenylphenyl)methoxy]-2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]hexan-2-yl]-4-phenyl-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Insoluble polystyrene-bound bis(oxazoline): batch and continuous-flow heterogeneous enantioselective glyoxylate–ene reaction

  摘要：

  The use of a new, insoluble polymer-bound bis(oxazoline) ligand (IPB-box) for the copper-catalyzed heterogeneous enantioselective glyoxylate-ene reaction is described. Good activity and ee values in the range 85-95% have been obtained during five to seven recycles, either in batch mode or under flow conditions, demonstrating also the recovery and reuse of the whole catalytically active copper complex. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.08.015
• 作为产物：
  描述：

  4-氯甲基苯乙烯 在 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 Toluene-4-sulfonic acid 4-(4-vinyl-benzyloxy)-butyl ester
  参考文献：
  名称：

  Insoluble polystyrene-bound bis(oxazoline): batch and continuous-flow heterogeneous enantioselective glyoxylate–ene reaction

  摘要：

  The use of a new, insoluble polymer-bound bis(oxazoline) ligand (IPB-box) for the copper-catalyzed heterogeneous enantioselective glyoxylate-ene reaction is described. Good activity and ee values in the range 85-95% have been obtained during five to seven recycles, either in batch mode or under flow conditions, demonstrating also the recovery and reuse of the whole catalytically active copper complex. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.08.015

文献信息

• An Insoluble Polymer-Bound Bis-Oxazoline Copper(II) Complex: A Highly Efficient Heterogeneous Catalyst for the Enantioselective Mukaiyama Aldol Reaction
  作者：Simonetta Orlandi、Alessandro Mandoli、Dario Pini、Piero Salvadori

  DOI：10.1002/1521-3773(20010702)40:13<2519::aid-anie2519>3.0.co;2-d

  日期：2001.7.2

  polystyrene-supported bis-oxazoline 1 forms a complex with copper(II)triflate that is a highly effective catalyst for the heterogeneously catalyzed enantioselective Mukaiyama aldol reaction of silylthioketene acetals with methyl pyruvate (ca. 90 % yield, ca. 90 % ee). The catalyst can be recovered by simple filtration and reused several times without a decline in enantioselectivity.

  聚苯乙烯负载的双恶唑啉1与三氟甲磺酸铜（II）形成络合物，是一种高效的催化剂，用于甲硫基乙烯酮缩醛与丙酮酸甲酯的异质催化对映选择性Mukaiyama醛醇缩合反应（产率约90％，ee约90％） 。可以通过简单的过滤来回收催化剂，并且可以重复使用几次而不会降低对映选择性。
• Insoluble polystyrene-bound bis(oxazoline): batch and continuous-flow heterogeneous enantioselective glyoxylate–ene reaction
  作者：Alessandro Mandoli、Simonetta Orlandi、Dario Pini、Piero Salvadori

  DOI：10.1016/j.tetasy.2004.08.015

  日期：2004.10

  The use of a new, insoluble polymer-bound bis(oxazoline) ligand (IPB-box) for the copper-catalyzed heterogeneous enantioselective glyoxylate-ene reaction is described. Good activity and ee values in the range 85-95% have been obtained during five to seven recycles, either in batch mode or under flow conditions, demonstrating also the recovery and reuse of the whole catalytically active copper complex. (C) 2004 Elsevier Ltd. All rights reserved.