benzyl N-[(2S,3S,4S)-1-cyano-3,4-bis(methoxymethoxy)hex-5-en-2-yl]-N-prop-2-enylcarbamate | 1393535-59-5

• 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: benzyl N-[(2S,3S,4S)-1-cyano-3,4-bis(methoxymethoxy)hex-5-en-2-yl]-N-prop-2-enylcarbamate
• CAS: 1393535-59-5
• 化学式: C₂₂H₃₀N₂O₆
• 分子量: 418.49
• InChiKey: UHGKPWMNMDHDFI-ACRUOGEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  90.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2S,3S,4S)-1-cyano-3,4-bis(methoxymethoxy)hex-5-en-2-yl]-N-prop-2-enylcarbamate 在 Grubbs catalyst first generation 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以80%的产率得到benzyl (2S,3S,4S)-2-(cyanomethyl)-3,4-bis(methoxymethoxy)-2,3,4,7-tetrahydroazepine-1-carboxylate
  参考文献：
  名称：

  Convenient strategy for the synthesis of highly functionalizable hydroxylated unsaturated azepanes

  摘要：

  A convenient approach to the construction of dihydroxylated unsaturated azepanes featuring a functional group (ethoxycarbonyl)methyl or (cyano)methyl at C-2 was achieved from a pent-4-enal synthon obtained in four steps from D-xylose. The key step of the sequence relied on the conjugate addition of allylamine to alpha,beta-unsaturated ester or nitrile, prepared by Wadsworth-Emmons olefination. Subsequent RCM afforded the target unsaturated azepanes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.053
• 作为产物：
  描述：

  、 氯甲酸苄酯 在 碳酸氢钠 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 13.0h， 生成 benzyl N-[(2S,3S,4S)-1-cyano-3,4-bis(methoxymethoxy)hex-5-en-2-yl]-N-prop-2-enylcarbamate 、 benzyl N-[(2R,3S,4S)-1-cyano-3,4-bis(methoxymethoxy)hex-5-en-2-yl]-N-prop-2-enylcarbamate
  参考文献：
  名称：

  Convenient strategy for the synthesis of highly functionalizable hydroxylated unsaturated azepanes

  摘要：

  A convenient approach to the construction of dihydroxylated unsaturated azepanes featuring a functional group (ethoxycarbonyl)methyl or (cyano)methyl at C-2 was achieved from a pent-4-enal synthon obtained in four steps from D-xylose. The key step of the sequence relied on the conjugate addition of allylamine to alpha,beta-unsaturated ester or nitrile, prepared by Wadsworth-Emmons olefination. Subsequent RCM afforded the target unsaturated azepanes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.053