2-(hydroxy[4-vinylphenyl][4-{1-methylethyl}phenyl]methyl)pyrrolidine-1-carboxylic acid tert-butyl ester | 481076-54-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(hydroxy[4-vinylphenyl][4-{1-methylethyl}phenyl]methyl)pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-[(4-ethenylphenyl)-hydroxy-(4-propan-2-ylphenyl)methyl]pyrrolidine-1-carboxylate
• CAS: 481076-54-4
• 化学式: C₂₇H₃₅NO₃
• 分子量: 421.58
• InChiKey: CJMSQJOPZMWBEP-BXXZMZEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  magnesium,propan-2-ylbenzene,bromide 生成 2-(hydroxy[4-vinylphenyl][4-{1-methylethyl}phenyl]methyl)pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Comparison of enantioselective reductions using bead and monolith ‘disk’ polymer formulations of CBS catalysts

  摘要：

  Two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst were prepared and examined. Polymeric beads, with the auxiliary bound in pendant and crosslinked fashion, were prepared utilizing an improved procedure based upon earlier work. Optimization of a procedure for ketone reduction gives results that match those in solution. Attempted reuse gave mixed results. For comparison purposes, CBS functionalized monoliths were formed and tested but performed poorly. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.048

文献信息

• Oxazaborolidines as Functional Monomers:  Ketone Reduction Using Polymer-Supported Corey, Bakshi, and Shibata Catalysts
  作者：Michael D. Price、Jennifer K. Sui、Mark J. Kurth、Neil E. Schore

  DOI：10.1021/jo026132n

  日期：2002.11.1

  The first two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst have been prepared. Functional monomers based structurally upon the original B-methylated catalyst have been used to prepare catalytic polymers containing the CBS moiety bound both in a pendant fashion and in the form of a cross-link. Enantioselective reductions of two prochiral ketones have been carried out using the original catalyst in the solution phase as well as the two solid-state systems. While the pendant-bound system shows reduced stereoselectivity, the cross-linked version affords enantioselectivities almost identical to those of the solution-phase model.