tris(2,6-diphenylbenzyl)silyl bromide | 308336-00-7

• 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: tris(2,6-diphenylbenzyl)silyl bromide
• 英文别名: Bromo-tris[(2,6-diphenylphenyl)methyl]silane
• CAS: 308336-00-7
• 化学式: C₅₇H₄₅BrSi
• 分子量: 837.974
• InChiKey: ZMPFLBMPLMOCTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.67
• 重原子数：
  59
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  tris(2,6-diphenylbenzyl)silyl bromide 在 silver trifluoromethanesulfonate 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 tris(2,6-diphenylbenzyl)silyl glyoxylate
  参考文献：
  名称：

  Synthetic utility of bowl-shaped tris(2,6-diphenyl-benzyl)silyl glyoxylate as a stable glyoxylate: application to highly diastereoselective aldol reactions

  摘要：

  A stable glyoxylate can be successfully applied to both syn- and anti-selective aldol reactions by using two different kinds of ordinary Lewis acids. Thus, treatment of bowl-shaped tris(2,6-diphenylbenzyl)silyl glyoxylate 1 with enol silyl ether under the influence of BF3.OEt2 gave syn-aldol product, while the use of TiCl4 afforded anti-aldol product with >97% selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02557-1
• 作为产物：
  描述：

  tris(2,6-diphenylbenzyl)silane 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以79%的产率得到tris(2,6-diphenylbenzyl)silyl bromide
  参考文献：
  名称：

  三（2,6-二苯基苄基）甲硅烷基作为羧酸的新型高效保护剂：此类羧酸酯对常见亲核试剂和碱基的异常行为

  摘要：

  DOI：

  10.1021/ja001940m

文献信息

• Synthetic utility of bowl-shaped tris(2,6-diphenyl-benzyl)silyl glyoxylate as a stable glyoxylate: application to highly diastereoselective aldol reactions
  作者：Seiji Shirakawa、Keiji Maruoka

  DOI：10.1016/s0040-4039(02)02557-1

  日期：2003.1

  A stable glyoxylate can be successfully applied to both syn- and anti-selective aldol reactions by using two different kinds of ordinary Lewis acids. Thus, treatment of bowl-shaped tris(2,6-diphenylbenzyl)silyl glyoxylate 1 with enol silyl ether under the influence of BF3.OEt2 gave syn-aldol product, while the use of TiCl4 afforded anti-aldol product with >97% selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Tris(2,6-diphenylbenzyl)silyl Group as a New and Highly Effective Protector for Carboxylic Acids:  Unusual Behavior of Such Carboxylic Esters toward Common Nucleophiles and Bases
  作者：Atsuko Iwasaki、Yuichiro Kondo、Keiji Maruoka

  DOI：10.1021/ja001940m

  日期：2000.10.1