benzyl N-[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyhex-5-en-2-yl]-N-[phenylmethoxycarbonyl(prop-2-enyl)amino]carbamate | 1050654-54-0

• 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: benzyl N-[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyhex-5-en-2-yl]-N-[phenylmethoxycarbonyl(prop-2-enyl)amino]carbamate
• CAS: 1050654-54-0
• 化学式: C₃₁H₄₄N₂O₅Si
• 分子量: 552.786
• InChiKey: GVIPMTHRVFSILX-NAKRPHOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.72
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyhex-5-en-2-yl]-N-[phenylmethoxycarbonyl(prop-2-enyl)amino]carbamate 在 Cl₂-Ru(PCy₃)2=CHPh 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以92%的产率得到dibenzyl (3R,4S,6Z)-4-[tert-butyl(dimethyl)silyl]oxy-3-methyl-3,4,5,8-tetrahydrodiazocine-1,2-dicarboxylate
  参考文献：
  名称：

  Organocatalytic α-amination–allylation-RCM strategy: enantioselective synthesis of cyclic hydrazines

  摘要：

  A highly enantioselective method for the synthesis of cyclic hydrazines by using organocatalytic alpha-amination-allylation-RCM strategy is described. Proline-catalyzed alpha-amination of aldehydes followed by indium-mediated one-pot allylation of the crude alpha-hydrazino aldehydes produces 1,2-aminoalcohols in high enantio- and diastereoselectivities. The 1,2-aminoalcohols are further converted into cyclic hydrazines by using ring-closing metathesis (RCM) reaction. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.004
• 作为产物：
  描述：

  dibenzyl 1-((2R,3S)-3-hydroxyhex-5-en-2-yl)hydrazine-1,2-dicarboxylate 、 叔丁基二甲硅基三氟甲磺酸酯 、 3-溴丙烯 在 2,6-二甲基吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以76%的产率得到benzyl N-[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyhex-5-en-2-yl]-N-[phenylmethoxycarbonyl(prop-2-enyl)amino]carbamate
  参考文献：
  名称：

  Organocatalytic α-amination–allylation-RCM strategy: enantioselective synthesis of cyclic hydrazines

  摘要：

  A highly enantioselective method for the synthesis of cyclic hydrazines by using organocatalytic alpha-amination-allylation-RCM strategy is described. Proline-catalyzed alpha-amination of aldehydes followed by indium-mediated one-pot allylation of the crude alpha-hydrazino aldehydes produces 1,2-aminoalcohols in high enantio- and diastereoselectivities. The 1,2-aminoalcohols are further converted into cyclic hydrazines by using ring-closing metathesis (RCM) reaction. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.004

文献信息

• Organocatalytic α-amination–allylation-RCM strategy: enantioselective synthesis of cyclic hydrazines
  作者：Aram Lim、Jung Hoon Choi、Jinsung Tae

  DOI：10.1016/j.tetlet.2008.06.004

  日期：2008.8

  A highly enantioselective method for the synthesis of cyclic hydrazines by using organocatalytic alpha-amination-allylation-RCM strategy is described. Proline-catalyzed alpha-amination of aldehydes followed by indium-mediated one-pot allylation of the crude alpha-hydrazino aldehydes produces 1,2-aminoalcohols in high enantio- and diastereoselectivities. The 1,2-aminoalcohols are further converted into cyclic hydrazines by using ring-closing metathesis (RCM) reaction. (C) 2008 Elsevier Ltd. All rights reserved.