tert-butyl (4S,5S)-4-(2-allyloxy-4-methoxyphenyl)-2-trichloromethyl-5,6-dihydro-4H-1,3-oxazin-5-ylcarbamate | 925703-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl (4S,5S)-4-(2-allyloxy-4-methoxyphenyl)-2-trichloromethyl-5,6-dihydro-4H-1,3-oxazin-5-ylcarbamate
• 英文别名: tert-butyl N-[(4S,5S)-4-(4-methoxy-2-prop-2-enoxyphenyl)-2-(trichloromethyl)-5,6-dihydro-4H-1,3-oxazin-5-yl]carbamate
• CAS: 925703-62-4
• 化学式: C₂₀H₂₅Cl₃N₂O₅
• 分子量: 479.788
• InChiKey: ARUPRFONHRHFDZ-ZBFHGGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S,5S)-4-(2-allyloxy-4-methoxyphenyl)-2-trichloromethyl-5,6-dihydro-4H-1,3-oxazin-5-ylcarbamate 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以100%的产率得到N-((S)-(2-allyloxy-4-methoxyphenyl)((S)-2-oxooxazolidin-4-yl)methyl)-2,2,2-trichloroacetamide
  参考文献：
  名称：

  Synthesis of Protected Chiral Vicinal Diaminoalcohols by Diastereoselective Intramolecular Benzylic Substitution from Bistrichloroacetimidates

  摘要：

  An efficient synthesis of chiral dihydrooxazines (2) from 1-aryl-2-amino-propane-1,3-diols (1) via the corresponding bistrichloroacetimidate intermediates has been developed. In this transformation, one trichloroacetimidate acts as a leaving group and the other acts as a nucleophile. The cyclization proceeds through an S(N)1 mechanism to provide trans-dihydrooxazines with complete diastereoselectivity irrespective of the absolute configuration of the benzylic alcohol. The transformation of 2 into other selectively protected aminodiols is also documented.

  DOI：

  10.1021/ol0627202
• 作为产物：
  描述：

  (R)-(+)-3-Boc-2,2-二甲基恶唑啉-4-甲醛 在 titanium(IV) isopropylate 、 potassium carbonate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 39.0h， 生成 tert-butyl (4S,5S)-4-(2-allyloxy-4-methoxyphenyl)-2-trichloromethyl-5,6-dihydro-4H-1,3-oxazin-5-ylcarbamate
  参考文献：
  名称：

  Synthesis of Protected Chiral Vicinal Diaminoalcohols by Diastereoselective Intramolecular Benzylic Substitution from Bistrichloroacetimidates

  摘要：

  An efficient synthesis of chiral dihydrooxazines (2) from 1-aryl-2-amino-propane-1,3-diols (1) via the corresponding bistrichloroacetimidate intermediates has been developed. In this transformation, one trichloroacetimidate acts as a leaving group and the other acts as a nucleophile. The cyclization proceeds through an S(N)1 mechanism to provide trans-dihydrooxazines with complete diastereoselectivity irrespective of the absolute configuration of the benzylic alcohol. The transformation of 2 into other selectively protected aminodiols is also documented.

  DOI：

  10.1021/ol0627202

文献信息

• Synthesis of Protected Chiral Vicinal Diaminoalcohols by Diastereoselective Intramolecular Benzylic Substitution from Bistrichloroacetimidates
  作者：Christophe Rondot、Pascal Retailleau、Jieping Zhu

  DOI：10.1021/ol0627202

  日期：2007.1.1

  An efficient synthesis of chiral dihydrooxazines (2) from 1-aryl-2-amino-propane-1,3-diols (1) via the corresponding bistrichloroacetimidate intermediates has been developed. In this transformation, one trichloroacetimidate acts as a leaving group and the other acts as a nucleophile. The cyclization proceeds through an S(N)1 mechanism to provide trans-dihydrooxazines with complete diastereoselectivity irrespective of the absolute configuration of the benzylic alcohol. The transformation of 2 into other selectively protected aminodiols is also documented.