tert-butyl (1R,2R)-1-(2-allyloxy-4,5-dimethoxy-3-methylphenyl)-1,3-dihydroxypropan-2-ylcarbamate | 925704-02-5

• 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: tert-butyl (1R,2R)-1-(2-allyloxy-4,5-dimethoxy-3-methylphenyl)-1,3-dihydroxypropan-2-ylcarbamate
• 英文别名: tert-butyl N-[(1R,2R)-1-(4,5-dimethoxy-3-methyl-2-prop-2-enoxyphenyl)-1,3-dihydroxypropan-2-yl]carbamate
• CAS: 925704-02-5
• 化学式: C₂₀H₃₁NO₇
• 分子量: 397.469
• InChiKey: IBWWJGJQKIXGRT-GDBMZVCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,2R)-1-(2-allyloxy-4,5-dimethoxy-3-methylphenyl)-1,3-dihydroxypropan-2-ylcarbamate 在 三氟甲磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 21.5h， 生成 (1R,2R)-1-(2-allyloxy-4,5-dimethoxy-3-methylphenyl)-2-(benzyloxycarbonylamino)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
• 作为产物：
  描述：

  2-methyl-3,4-dimethoxyphenol 在 甲基氯化镁 、 potassium carbonate 、 对甲苯磺酸 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 33.17h， 生成 tert-butyl (1R,2R)-1-(2-allyloxy-4,5-dimethoxy-3-methylphenyl)-1,3-dihydroxypropan-2-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.