(3aS,4R,5S,7R,7aR)-7a,8,8-Trimethyl-1-phenyl-4-((S)-3-phenyl-4,5-dihydro-isoxazole-5-carbonyloxy)-3a,4,5,6,7,7a-hexahydro-1H-5,7-methano-indazole-3-carboxylic acid methyl ester | 861942-54-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3aS,4R,5S,7R,7aR)-7a,8,8-Trimethyl-1-phenyl-4-((S)-3-phenyl-4,5-dihydro-isoxazole-5-carbonyloxy)-3a,4,5,6,7,7a-hexahydro-1H-5,7-methano-indazole-3-carboxylic acid methyl ester
• 英文别名: [(1R,2R,6S,7R,8S)-5-methoxycarbonyl-2,9,9-trimethyl-3-phenyl-3,4-diazatricyclo[6.1.1.02,6]dec-4-en-7-yl] (5S)-3-phenyl-4,5-dihydro-1,2-oxazole-5-carboxylate
• CAS: 861942-54-3
• 化学式: C₂₉H₃₁N₃O₅
• 分子量: 501.582
• InChiKey: IHVMKAXOOWSZFZ-XNNFTDICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  89.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3aS,4R,5S,7R,7aR)-7a,8,8-Trimethyl-1-phenyl-4-((S)-3-phenyl-4,5-dihydro-isoxazole-5-carbonyloxy)-3a,4,5,6,7,7a-hexahydro-1H-5,7-methano-indazole-3-carboxylic acid methyl ester 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 34.0h， 生成 methyl (1R,2R,6S,7R,8S)-2,9,9-trimethyl-3-phenyl-7-prop-2-enoyloxy-3,4-diazatricyclo[6.1.1.02,6]dec-4-ene-5-carboxylate
  参考文献：
  名称：

  A bicyclo[3.1.1]heptano[4,3-c]pyrazole derived chiral auxiliary for dipolar cycloadditions

  摘要：

  Starting form naturally occurring (S)-cis-verbenol 1 and (1R)-(-)-myrtenol 2, we synthesised enantiopure bicyclo[3.1.1]heptano[4.3-c]pyrazole derivatives 7 and 8 via a stereoselective nitrilimine cycloaddition as the key step. The effectiveness of the above skeleton as a new chiral auxiliary was evaluated towards the 1,3-dipolar cycloadditions of nitrile oxides and nitrilimines. Basic hydrolysis of the major cycloadducts gave enantiopure 5-carboxy-4,5-dihydroisoxazole (S)-(+)-19 and 5-carboxy-4,5-dihydropyrazole (S)-(+)-20, respectively, which Lire of potential interest as chiral building blocks. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.014
• 作为产物：
  描述：

  methyl 2-chloro-2-(2-phenylhydrazono)acetate 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 114.0h， 生成 (3aS,4R,5S,7R,7aR)-7a,8,8-Trimethyl-1-phenyl-4-((S)-3-phenyl-4,5-dihydro-isoxazole-5-carbonyloxy)-3a,4,5,6,7,7a-hexahydro-1H-5,7-methano-indazole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  A bicyclo[3.1.1]heptano[4,3-c]pyrazole derived chiral auxiliary for dipolar cycloadditions

  摘要：

  Starting form naturally occurring (S)-cis-verbenol 1 and (1R)-(-)-myrtenol 2, we synthesised enantiopure bicyclo[3.1.1]heptano[4.3-c]pyrazole derivatives 7 and 8 via a stereoselective nitrilimine cycloaddition as the key step. The effectiveness of the above skeleton as a new chiral auxiliary was evaluated towards the 1,3-dipolar cycloadditions of nitrile oxides and nitrilimines. Basic hydrolysis of the major cycloadducts gave enantiopure 5-carboxy-4,5-dihydroisoxazole (S)-(+)-19 and 5-carboxy-4,5-dihydropyrazole (S)-(+)-20, respectively, which Lire of potential interest as chiral building blocks. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.014

文献信息

• A bicyclo[3.1.1]heptano[4,3-c]pyrazole derived chiral auxiliary for dipolar cycloadditions
  作者：Giorgio Molteni、Paola Del Buttero

  DOI：10.1016/j.tetasy.2005.04.014

  日期：2005.6

  Starting form naturally occurring (S)-cis-verbenol 1 and (1R)-(-)-myrtenol 2, we synthesised enantiopure bicyclo[3.1.1]heptano[4.3-c]pyrazole derivatives 7 and 8 via a stereoselective nitrilimine cycloaddition as the key step. The effectiveness of the above skeleton as a new chiral auxiliary was evaluated towards the 1,3-dipolar cycloadditions of nitrile oxides and nitrilimines. Basic hydrolysis of the major cycloadducts gave enantiopure 5-carboxy-4,5-dihydroisoxazole (S)-(+)-19 and 5-carboxy-4,5-dihydropyrazole (S)-(+)-20, respectively, which Lire of potential interest as chiral building blocks. (c) 2005 Elsevier Ltd. All rights reserved.