(1R,2R)-1-(2-allyloxy-5-tert-butylphenyl)-2-(tert-butoxycarbonylamino)propane-1,3-diyl bis(2,2,2-trichloroacetimidate) | 925704-34-3

• 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: (1R,2R)-1-(2-allyloxy-5-tert-butylphenyl)-2-(tert-butoxycarbonylamino)propane-1,3-diyl bis(2,2,2-trichloroacetimidate)
• CAS: 925704-34-3
• 化学式: C₂₅H₃₃Cl₆N₃O₅
• 分子量: 668.272
• InChiKey: AMQDKXWHCZOKEA-SJLPKXTDSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  113.72
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-(2-allyloxy-5-tert-butylphenyl)-2-(tert-butoxycarbonylamino)propane-1,3-diyl bis(2,2,2-trichloroacetimidate) 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以43%的产率得到tert-butyl (4S,5S)-4-(5-tert-butyl-2-(allyloxy)phenyl)-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
• 作为产物：
  描述：

  (R)-(+)-3-Boc-2,2-二甲基恶唑啉-4-甲醛 在 甲基氯化镁 、 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 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 34.17h， 生成 (1R,2R)-1-(2-allyloxy-5-tert-butylphenyl)-2-(tert-butoxycarbonylamino)propane-1,3-diyl bis(2,2,2-trichloroacetimidate)
  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