tert-butyl (1R,2R)-1-(5-(allyloxy)benzo[d][1,3]dioxol-6-yl)-1,3-dihydroxypropan-2-ylcarbamate | 925703-99-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: tert-butyl (1R,2R)-1-(5-(allyloxy)benzo[d][1,3]dioxol-6-yl)-1,3-dihydroxypropan-2-ylcarbamate
• CAS: 925703-99-7
• 化学式: C₁₈H₂₅NO₇
• 分子量: 367.399
• InChiKey: HAPUPKCWNBKWGJ-MLGOLLRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106.48
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,2R)-1-(5-(allyloxy)benzo[d][1,3]dioxol-6-yl)-1,3-dihydroxypropan-2-ylcarbamate 、 三氯乙腈 在 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 1.0h， 以78%的产率得到tert-butyl (4S,5S)-4-(5-(allyloxy)benzo[d][1,3]dioxol-6-yl)-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：

  tert-butyl (R)-4-((R)-hydroxy(6-hydroxybenzo[d][1,3]dioxol-5-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate 在 potassium carbonate 、 对甲苯磺酸 、 sodium iodide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 18.0h， 生成 tert-butyl (1R,2R)-1-(5-(allyloxy)benzo[d][1,3]dioxol-6-yl)-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