stearic acid-((1R)-menthyl ester) | 93919-01-8

• 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: stearic acid-((1R)-menthyl ester)
• 英文别名: Stearinsaeure-((1R)-menthylester)；(-)-Menthyl Stearate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] octadecanoate
• CAS: 93919-01-8
• 化学式: C₂₈H₅₄O₂
• 分子量: 422.736
• InChiKey: UFFYOHVNDSTCTL-KWXIBIRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  30
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  stearic acid-((1R)-menthyl ester) 生成 (+)-反式-对-薄荷-2-烯 、 (1R)-menth-3-ene
  参考文献：
  名称：

  Wibaut; Beyermann; van Leeuwen, Recueil des Travaux Chimiques des Pays-Bas, 1952, vol. 71, p. 1027,1031, 1032

  摘要：

  DOI：
• 作为产物：
  描述：

  L-薄荷醇 、 硬脂酸 在 cerium(IV) trifluoromethanesulfonate 作用下， 反应 2.0h， 以92%的产率得到stearic acid-((1R)-menthyl ester)
  参考文献：
  名称：

  醇、羧酸的催化酯化和与三氟甲磺酸铈 (IV) 的酯交换反应

  摘要：

  醇与乙酸、氯乙酸、三氟乙酸、丙酸、硬脂酸和苯甲酸的酯化反应用 Ce(OTf)4 在溶剂中或在无溶剂条件下以高产率催化。伯醇和仲醇的甲酰化和乙酰化也很容易在甲酸乙酯和乙酸乙酯中实现。在 (-)-薄荷醇的乙酰化和甲酰化中观察到构型的高保留。

  DOI：

  10.1246/bcsj.72.455

文献信息

• Shekarriz, Marzieh; Taghipoor, Sohrab; Khalili, Ali Asghar, Journal of Chemical Research - Part S, 2003, # 3, p. 172 - 173
  作者：Shekarriz, Marzieh、Taghipoor, Sohrab、Khalili, Ali Asghar、Jamarani, Mohammad Soleymani

  DOI：——

  日期：——
• Enzymatic esterification of (−)-menthol with fatty acids in solvent by a commercial lipase from <i>Candida rugosa</i>
  作者：Banu Babali、H. Ay§e Aksoy、Melek Tüter、Guldem Ustun

  DOI：10.1007/s11746-001-0219-x

  日期：2001.1

  AbstractEsterification of (−)‐menthol with fatty acids in isooctane was successfully catalyzed using a commercial lipase, Lipase AY “Amano” 30 from Candida rugosa in original powder form. The esterification reactions were performed to elucidate the effects of temperature, enzyme load, molar ratio of (−)‐menthol/fatty acid, and fatty acid type, keeping the (−)‐menthol concentration at 200 mM. At the optimal conditions for (−)‐menthol esterification, determined at a (−)‐menthol/lauric acid molar ratio of 1∶1 and 35°C [1.5 g enzyme/g (−)‐menthol, 0.1 g molecular sieves], the molar conversion of (−)‐menthol after 48 h reached 93%. After 24h, the lowest and the highest molar conversions of fatty acids at 2∶1 molar ratio were obtained with myristic acid (71%) and margaric acid (98%), respectively. After 48 h, the molar conversions of lauric acid at molar ratios 2∶1, 1∶1, and 1∶2 were 98, 93, and 49%, respectively.
• Catalytic Esterification of Alcohols, Carboxylic Acids and Transesterification Reactions with Cerium(IV) Triflate
  作者：Nasser Iranpoor、Marzieh Shekarriz

  DOI：10.1246/bcsj.72.455

  日期：1999.3

  reactions of alcohols with acetic, chloroacetic, trifluoroacetic, propionic, stearic, and benzoic acids were catalyzed with Ce(OTf)4 in a solvent or under solvent-free conditions with high yields. The formylation and acetylation of primary and secondary alcohols were also easily achieved in ethyl formate and ethyl acetate. A high retention of the configuration was observed in the acetylation and formylation

  醇与乙酸、氯乙酸、三氟乙酸、丙酸、硬脂酸和苯甲酸的酯化反应用 Ce(OTf)4 在溶剂中或在无溶剂条件下以高产率催化。伯醇和仲醇的甲酰化和乙酰化也很容易在甲酸乙酯和乙酸乙酯中实现。在 (-)-薄荷醇的乙酰化和甲酰化中观察到构型的高保留。
• Wibaut; Beyermann; van Leeuwen, Recueil des Travaux Chimiques des Pays-Bas, 1952, vol. 71, p. 1027,1031, 1032
  作者：Wibaut、Beyermann、van Leeuwen

  DOI：——

  日期：——