(S)-1-p-Tolyl-4,5-dihydro-1H-pyrazole-3,5-dicarboxylic acid 5-((3aS,5R,7R,7aR)-3-methoxycarbonyl-8,8-dimethyl-1-phenyl-1,3a,4,5,6,7-hexahydro-5,7-methano-indazol-7a-ylmethyl) ester 3-methyl ester | 861942-52-1

• 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: (S)-1-p-Tolyl-4,5-dihydro-1H-pyrazole-3,5-dicarboxylic acid 5-((3aS,5R,7R,7aR)-3-methoxycarbonyl-8,8-dimethyl-1-phenyl-1,3a,4,5,6,7-hexahydro-5,7-methano-indazol-7a-ylmethyl) ester 3-methyl ester
• CAS: 861942-52-1
• 化学式: C₃₂H₃₆N₄O₆
• 分子量: 572.661
• InChiKey: JESVVJKGAGEPGI-LBVZOOFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  42.0
• 可旋转键数：
  7.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  110.1
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (S)-1-p-Tolyl-4,5-dihydro-1H-pyrazole-3,5-dicarboxylic acid 5-((3aS,5R,7R,7aR)-3-methoxycarbonyl-8,8-dimethyl-1-phenyl-1,3a,4,5,6,7-hexahydro-5,7-methano-indazol-7a-ylmethyl) ester 3-methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以90%的产率得到(S)-3,5-dicarboxy-4,5-dihydropyrazole
  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：

  (3aS,5R,7R,7aR)-7a-Hydroxymethyl-8,8-dimethyl-1-phenyl-3a,4,5,6,7,7a-hexahydro-1H-5,7-methano-indazole-3-carboxylic acid methyl ester 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 54.0h， 生成 (S)-1-p-Tolyl-4,5-dihydro-1H-pyrazole-3,5-dicarboxylic acid 5-((3aS,5R,7R,7aR)-3-methoxycarbonyl-8,8-dimethyl-1-phenyl-1,3a,4,5,6,7-hexahydro-5,7-methano-indazol-7a-ylmethyl) ester 3-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