(S)-2-(Benzhydrylidene-amino)-5-trimethylsilanyl-pent-4-ynoic acid tert-butyl ester

• 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: (S)-2-(Benzhydrylidene-amino)-5-trimethylsilanyl-pent-4-ynoic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-(benzhydrylideneamino)-5-trimethylsilylpent-4-ynoate
• 化学式: C₂₅H₃₁NO₂Si
• 分子量: 405.612
• InChiKey: AVZLLOSZDAEFAZ-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴-1-三甲基硅基-1-丙炔 、 N-二苯亚甲基-甘氨酸叔丁酯 在 氢氧化钾 、 O-All-N-(1',8'-di-F-anthracenylmethyl)hydrocinchonidinium Br 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 11.0h， 以92%的产率得到(S)-2-(Benzhydrylidene-amino)-5-trimethylsilanyl-pent-4-ynoic acid tert-butyl ester
  参考文献：
  名称：

  Highly selective glycine phase-transfer catalysis using fluoroanthracenylmethyl cinchonidine catalysts

  摘要：

  Fluoroanthracenylmethyl cinchonidine phase-transfer catalysts have been produced and explored for asymmetric glycine alkylation. The fluoroanthracenylmethyl precursors were made from aryloxazolidinones and aldehydes using an efficient electrophilic substitution with phosphorous pentoxide. The cinchonidine catalysts promote highly selective glycine alkylation under mild conditions. The 1,8-difluoroanthracenyl-10-methyl catalyst 6 (10 mol %) in toluene/THF with 50% aqueous KOH (-20 ° C) promoted benzylation of glycine 1 to give 2 in 86% yield, 98% ee. Other electrophiles also gave excellent selectivity and reactivity. © 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.185

文献信息

• Highly selective glycine phase-transfer catalysis using fluoroanthracenylmethyl cinchonidine catalysts
  作者：Merritt B. Andrus、Zhifeng Ye、Jiuqing Zhang

  DOI：10.1016/j.tetlet.2005.03.185

  日期：2005.5

  Fluoroanthracenylmethyl cinchonidine phase-transfer catalysts have been produced and explored for asymmetric glycine alkylation. The fluoroanthracenylmethyl precursors were made from aryloxazolidinones and aldehydes using an efficient electrophilic substitution with phosphorous pentoxide. The cinchonidine catalysts promote highly selective glycine alkylation under mild conditions. The 1,8-difluoroanthracenyl-10-methyl catalyst 6 (10 mol %) in toluene/THF with 50% aqueous KOH (-20 ° C) promoted benzylation of glycine 1 to give 2 in 86% yield, 98% ee. Other electrophiles also gave excellent selectivity and reactivity. © 2005 Elsevier Ltd. All rights reserved.