phenyl N-benzyl-N-(oxiran-2-ylmethyl)carbamate | 474670-40-1

• 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: phenyl N-benzyl-N-(oxiran-2-ylmethyl)carbamate
• CAS: 474670-40-1
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: AIBHHYBLERDRFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  42.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenyl N-benzyl-N-(oxiran-2-ylmethyl)carbamate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.25h， 生成 3-Benzyl-5-(3-trimethylsilylprop-2-ynyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Alkynyliodonium Salts in Organic Synthesis. Development of a Unified Strategy for the Syntheses of (−)-Agelastatin A and (−)-Agelastatin B

  摘要：

  The total syntheses of natural agelastatin A and agelastatin B were accomplished via a strategy that utilized an alkynyliodonium. salt --> alkylidenecarbene --> cyclopentene transformation to convert a relatively simple amino alcohol derivative to the functionalized core of the agelastatin system. Subsequent manipulations delivered debromoagelastatin, which served as a precursor to both agelastatin A and agelastatin B. Alkylidenecarbene insertion chemoselectivity issues were explored en route to the final targets.

  DOI：

  10.1021/jo026287v
• 作为产物：
  描述：

  N-烯丙基苄胺 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 phenyl N-benzyl-N-(oxiran-2-ylmethyl)carbamate
  参考文献：
  名称：

  Alkynyliodonium Salts in Organic Synthesis. Development of a Unified Strategy for the Syntheses of (−)-Agelastatin A and (−)-Agelastatin B

  摘要：

  The total syntheses of natural agelastatin A and agelastatin B were accomplished via a strategy that utilized an alkynyliodonium. salt --> alkylidenecarbene --> cyclopentene transformation to convert a relatively simple amino alcohol derivative to the functionalized core of the agelastatin system. Subsequent manipulations delivered debromoagelastatin, which served as a precursor to both agelastatin A and agelastatin B. Alkylidenecarbene insertion chemoselectivity issues were explored en route to the final targets.

  DOI：

  10.1021/jo026287v

文献信息

• Alkynyliodonium Salts in Organic Synthesis. Development of a Unified Strategy for the Syntheses of (−)-Agelastatin A and (−)-Agelastatin B
  作者：Ken S. Feldman、Joe C. Saunders、Michelle Laci Wrobleski

  DOI：10.1021/jo026287v

  日期：2002.10.1

  The total syntheses of natural agelastatin A and agelastatin B were accomplished via a strategy that utilized an alkynyliodonium. salt --> alkylidenecarbene --> cyclopentene transformation to convert a relatively simple amino alcohol derivative to the functionalized core of the agelastatin system. Subsequent manipulations delivered debromoagelastatin, which served as a precursor to both agelastatin A and agelastatin B. Alkylidenecarbene insertion chemoselectivity issues were explored en route to the final targets.