tert-butyl (1R,2R)-1-(1-allyloxy-4-methoxynaphthalen-2-yl)-1,3-dihydroxypropan-2-ylcarbamate | 925704-08-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl (1R,2R)-1-(1-allyloxy-4-methoxynaphthalen-2-yl)-1,3-dihydroxypropan-2-ylcarbamate
• CAS: 925704-08-1
• 化学式: C₂₂H₂₉NO₆
• 分子量: 403.475
• InChiKey: SRUMNMXGJSNQEB-IEBWSBKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  97.25
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,2R)-1-(1-allyloxy-4-methoxynaphthalen-2-yl)-1,3-dihydroxypropan-2-ylcarbamate 在 甲烷磺酸 、 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 17.0h， 生成 tert-butyl (4S,5S)-4-(1-allyloxy-4-methoxynaphthalen-2-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：

  在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 tert-butyl (1R,2R)-1-(1-allyloxy-4-methoxynaphthalen-2-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