(1R,2R)-1-(2-allyloxy-4,5-dimethoxy-3-methylphenyl)-2-(tert-butoxycarbonylamino)propane-1,3-diyl bis(2,2,2-trichloroacetimidate) | 925703-64-6

• 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-4,5-dimethoxy-3-methylphenyl)-2-(tert-butoxycarbonylamino)propane-1,3-diyl bis(2,2,2-trichloroacetimidate)
• 英文别名: [(2R,3R)-3-(4,5-dimethoxy-3-methyl-2-prop-2-enoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(2,2,2-trichloroethanimidoyl)oxypropyl] 2,2,2-trichloroethanimidate
• CAS: 925703-64-6
• 化学式: C₂₄H₃₁Cl₆N₃O₇
• 分子量: 686.244
• InChiKey: AKZSXVKFVMTMFD-RDTXWAMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-(2-allyloxy-4,5-dimethoxy-3-methylphenyl)-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71%的产率得到tert-butyl (4S,5S)-4-(2-allyloxy-4,5-dimethoxy-3-methylphenyl)-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-4,5-dimethoxy-3-methylphenyl)-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

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.