dimethyl 2-[(1R,5R)-5-hydroxy-4-methylcyclohex-3-enyl]malonate | 1256634-28-2

• 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: dimethyl 2-[(1R,5R)-5-hydroxy-4-methylcyclohex-3-enyl]malonate
• CAS: 1256634-28-2
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: VXICGGUZJWHADC-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2-[(1R,5R)-5-hydroxy-4-methylcyclohex-3-enyl]malonate 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以86%的产率得到dimethyl (+/-)-2-[(1R,5S)-5-iodo-4-methylcyclohex-3-enyl]malonate
  参考文献：
  名称：

  Synthesis of diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6-dicarboxylate by Pd-catalyzed intramolecular allylic alkylation. Stereoselective preparation of its optically homogeneous form from R-(−)-carvone

  摘要：

  A new route to racemic diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6-dicarboxylate (+/-)-1a by means of a palladium-catalyzed intramolecular allylic alkylation exercised on malonate-ester derivatives has been developed from R-(-)-carvone. The stereocontrolled synthesis of the enantiomerically pure (-)-1b by application of a six-step reactions sequence with a 28% overall yield from acetal 8, has been accomplished. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.051
• 作为产物：
  描述：

  dimethyl 2-[(R)-4-methyl-5-oxocyclohex-3-enyl]-malonate 在 sodium tetrahydroborate 、 cerium(III) chloride 、 水 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 0.25h， 以100%的产率得到dimethyl 2-[(1R,5R)-5-hydroxy-4-methylcyclohex-3-enyl]malonate
  参考文献：
  名称：

  Synthesis of diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6-dicarboxylate by Pd-catalyzed intramolecular allylic alkylation. Stereoselective preparation of its optically homogeneous form from R-(−)-carvone

  摘要：

  A new route to racemic diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6-dicarboxylate (+/-)-1a by means of a palladium-catalyzed intramolecular allylic alkylation exercised on malonate-ester derivatives has been developed from R-(-)-carvone. The stereocontrolled synthesis of the enantiomerically pure (-)-1b by application of a six-step reactions sequence with a 28% overall yield from acetal 8, has been accomplished. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.051