3-O-[(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] 5-O-methyl (3S)-2-(4-methylphenyl)-3,4-dihydropyrazole-3,5-dicarboxylate | 861942-50-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-O-[(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] 5-O-methyl (3S)-2-(4-methylphenyl)-3,4-dihydropyrazole-3,5-dicarboxylate
• CAS: 861942-50-9
• 化学式: C₃₂H₃₆N₄O₆
• 分子量: 572.661
• InChiKey: JMOHTUNIYQEDOB-PSQGQZDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-[(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] 5-O-methyl (3S)-2-(4-methylphenyl)-3,4-dihydropyrazole-3,5-dicarboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以86%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：

  methyl 2-chloro-2-(2-phenylhydrazono)acetate 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 102.0h， 生成 3-O-[(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] 5-O-methyl (3S)-2-(4-methylphenyl)-3,4-dihydropyrazole-3,5-dicarboxylate
  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