diethyl 2-(2-(p-tolyl)propyl)malonate | 1413723-28-0

• 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: diethyl 2-(2-(p-tolyl)propyl)malonate
• 英文别名: Diethyl (S)-2-(2-(p-Tolyl)propyl)malonate；diethyl 2-[(2S)-2-(4-methylphenyl)propyl]propanedioate
• CAS: 1413723-28-0
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: TXJBXKONOCWPEM-ZDUSSCGKSA-N

物化性质

• 沸点：
  379.1±37.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  diethyl 2-(2-(p-tolyl)propyl)malonate 在 水 、 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以78%的产率得到(4S)-(4-methylphenyl)pentanoic acid
  参考文献：
  名称：

  Enantioselective synthesis of the essential oil and pheromonal component ar-himachalene by a chiral pool and chirality induction approach

  摘要：

  The enantioselective synthesis of both isomers of ar-himachalene has been achieved starting from enantiomerically pure citronellal and p-methyl alpha-methyl styrene as an application of a chiral pool and chirality induction approach, respectively. The key reactions involved in the synthesis include the Sharpless asymmetric dihydroxylation for the induction of chirality at benzylic carbon bearing the methyl group and the use of a hypervalent iodine reagent or trimethylsilyldiazomethane (TMSCHN2) for the six to seven membered ring expansion. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.09.008
• 作为产物：
  描述：

  (R)-2-p-tolylpropan-1-ol 在 咪唑 、 碘 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 10.0h， 生成 diethyl 2-(2-(p-tolyl)propyl)malonate
  参考文献：
  名称：

  Enantioselective synthesis of the essential oil and pheromonal component ar-himachalene by a chiral pool and chirality induction approach

  摘要：

  The enantioselective synthesis of both isomers of ar-himachalene has been achieved starting from enantiomerically pure citronellal and p-methyl alpha-methyl styrene as an application of a chiral pool and chirality induction approach, respectively. The key reactions involved in the synthesis include the Sharpless asymmetric dihydroxylation for the induction of chirality at benzylic carbon bearing the methyl group and the use of a hypervalent iodine reagent or trimethylsilyldiazomethane (TMSCHN2) for the six to seven membered ring expansion. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.09.008

文献信息

• Enantioselective synthesis of the essential oil and pheromonal component ar-himachalene by a chiral pool and chirality induction approach
  作者：Subhash P. Chavan、Harshali S. Khatod

  DOI：10.1016/j.tetasy.2012.09.008

  日期：2012.10

  The enantioselective synthesis of both isomers of ar-himachalene has been achieved starting from enantiomerically pure citronellal and p-methyl alpha-methyl styrene as an application of a chiral pool and chirality induction approach, respectively. The key reactions involved in the synthesis include the Sharpless asymmetric dihydroxylation for the induction of chirality at benzylic carbon bearing the methyl group and the use of a hypervalent iodine reagent or trimethylsilyldiazomethane (TMSCHN2) for the six to seven membered ring expansion. (C) 2012 Elsevier Ltd. All rights reserved.