dimethyl 2-(4,4-dimethylhex-5-ynyl)malonate | 1610839-59-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl 2-(4,4-dimethylhex-5-ynyl)malonate
• 英文别名: Dimethyl 2-(4,4-dimethylhex-5-ynyl)propanedioate
• CAS: 1610839-59-2
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: HMUXHUALHOJNLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(4,4-dimethylhex-5-ynyl)malonate 在 pig liver esterase 、 potassium tert-butylate 、 水 、 四氯化锡 、 三乙胺 作用下， 以 aq. phosphate buffer 、 乙醚 、 二氯甲烷 为溶剂， 反应 87.0h， 生成 (S)-1-tert-butoxycarbonyl-3,3-dimethyl-2-methylenecyclohexane-1-carboxylic acid
  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 、 碘 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 、 三苯基膦 、 diborane(6) 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 28.08h， 生成 dimethyl 2-(4,4-dimethylhex-5-ynyl)malonate
  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