(1S,2S,3R,4R)-2-Benzoylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester | 178232-08-1

• 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: (1S,2S,3R,4R)-2-Benzoylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester
• CAS: 178232-08-1
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: FQZXLCJSBASYMQ-SZDLEDHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4R)-2-Benzoylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 28.0h， 生成 methyl (1R,2S,3R,4S)-2-benzamido-3-(1,2-dihydroxyethyl)bicyclo[2.2.1]heptane-2-carboxylate
  参考文献：
  名称：

  Diastereoselective synthesis of (1S,2S,3R,4R) and (1R,2S,3R,4S)-bicyclo[2.2.1]hept-2-amino-2,3-dicarboxylic acids: New conformationally-constrained (S)-aspartic acid analogues

  摘要：

  The title compounds were prepared from key intermediates readily obtained by the stereoselective Diels-Alder reaction of (Z)-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylene]-5(4H)-oxazolone, a chiral az-lactone derived from (R)-glyceraldehyde and cyclopentadiene. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00172-3
• 作为产物：
  描述：

  甲醇 、 (1S,2S,3R,4R)-3-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-bicyclo<2.2.1>-hept-5-en-2-spiro<4'<2'-phenyl-5'(4'H)-oxazolone>> 在 sodium methylate 作用下， 反应 0.5h， 以100%的产率得到(1S,2S,3R,4R)-2-Benzoylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Diastereoselective synthesis of (1S,2S,3R,4R) and (1R,2S,3R,4S)-bicyclo[2.2.1]hept-2-amino-2,3-dicarboxylic acids: New conformationally-constrained (S)-aspartic acid analogues

  摘要：

  The title compounds were prepared from key intermediates readily obtained by the stereoselective Diels-Alder reaction of (Z)-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylene]-5(4H)-oxazolone, a chiral az-lactone derived from (R)-glyceraldehyde and cyclopentadiene. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00172-3