(R)-methyl 1-hydroxymethyl-3,3-dimethyl-2-methylenecyclohexanecarboxylate | 1610839-61-6

• 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: (R)-methyl 1-hydroxymethyl-3,3-dimethyl-2-methylenecyclohexanecarboxylate
• 英文别名: methyl (1R)-1-(hydroxymethyl)-3,3-dimethyl-2-methylidenecyclohexane-1-carboxylate
• CAS: 1610839-61-6
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: AHJJBQGYUUVNJH-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methyl 1-hydroxymethyl-3,3-dimethyl-2-methylenecyclohexanecarboxylate 在 dimethyl sulfide borane 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以73%的产率得到(3aS,7aR)-7a-hydroxymethyl-4,4-dimethyl-hexahydroisobenzofuran-1(3H)-one
  参考文献：
  名称：

  Preparation of chiral building blocks for the enantioselective total synthesis of ent-kauranoids by the pig liver esterase-catalyzed asymmetric hydrolysis of a dialkyl malonate-type prochiral diester

  摘要：

  The preparation of chiral building blocks, suitable for use in the enantioselective total synthesis of kauranoids and ent-kauranoids, is reported herein. The pig liver esterase-catalyzed asymmetric hydrolysis of dimethyl 3,3-dimethyl-2-methylenecyclohexane-1,2-dicarboxylate, a malonate-type prochiral diester, afforded the corresponding half-ester in 96% yield and with 99% enantiomeric excess. The absolute configuration of the half-ester was determined by X-ray crystallographic analysis of its derivative and its enantiodivergent transformations are also described herein. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.01.019
• 作为产物：
  描述：

  2,2-dimethyl-4-pentenal ethylene acetal 在 咪唑 、 sodium tetrahydroborate 、 pig liver esterase 、 草酰氯 、 18-冠醚-6 、 水 、 碘 、 四氯化锡 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 N,N-二甲基甲酰胺 、 三苯基膦 、 diborane(6) 作用下， 以 四氢呋喃 、 甲醇 、 aq. phosphate buffer 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 58.08h， 生成 (R)-methyl 1-hydroxymethyl-3,3-dimethyl-2-methylenecyclohexanecarboxylate
  参考文献：
  名称：

  Preparation of chiral building blocks for the enantioselective total synthesis of ent-kauranoids by the pig liver esterase-catalyzed asymmetric hydrolysis of a dialkyl malonate-type prochiral diester

  摘要：

  The preparation of chiral building blocks, suitable for use in the enantioselective total synthesis of kauranoids and ent-kauranoids, is reported herein. The pig liver esterase-catalyzed asymmetric hydrolysis of dimethyl 3,3-dimethyl-2-methylenecyclohexane-1,2-dicarboxylate, a malonate-type prochiral diester, afforded the corresponding half-ester in 96% yield and with 99% enantiomeric excess. The absolute configuration of the half-ester was determined by X-ray crystallographic analysis of its derivative and its enantiodivergent transformations are also described herein. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.01.019