hexanoic acid (1R,2S,5R)-menthyl ester | 6070-16-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: hexanoic acid (1R,2S,5R)-menthyl ester
• 英文别名: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl hexanoate；menthyl hexanoate；hexanoic acid-((1R)-menthyl ester)；Hexansaeure-((1R)-menthylester)；(1beta,2alpha,4alpha)-p-Menth-2-yl hexanoate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] hexanoate
• CAS: 6070-16-2
• 化学式: C₁₆H₃₀O₂
• 分子量: 254.413
• InChiKey: VDXDHXCHHMIDPX-QLFBSQMISA-N

物化性质

• LogP：
  6.220 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  hexanoic acid (1R,2S,5R)-menthyl ester 在 水 作用下， 以 异辛烷 为溶剂， 生成 L-薄荷醇 、 己酸
  参考文献：
  名称：

  Quantitative analyses of biochemical kinetic resolution of enantiomers. 2. Enzyme-catalyzed esterifications in water-organic solvent biphasic systems

  摘要：

  DOI：

  10.1021/ja00243a040
• 作为产物：
  描述：

  己酰胺 、 L-薄荷醇 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 正辛烷 为溶剂， 反应 24.0h， 以72%的产率得到hexanoic acid (1R,2S,5R)-menthyl ester
  参考文献：
  名称：

  Scandium triflate catalyzed ester synthesis using primary amides

  摘要：

  A scandium triflate (ScOTf)(3) catalyzed methodology has been developed to synthesize esters from primary amides. Various primary and secondary aliphatic alcohols have been shown to react in n-heptane with a range of primary amides for 24 h. (C) 2014 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2014.10.124

文献信息

• Recyclable Hypervalent Iodine(III) Reagent Iodosodilactone as an Efficient Coupling Reagent for Direct Esterification, Amidation, and Peptide Coupling
  作者：Jun Tian、Wen-Chao Gao、Dong-Mei Zhou、Chi Zhang

  DOI：10.1021/ol301085v

  日期：2012.6.15

  hypervalent iodine(III) reagent plays a novel role as an efficient coupling reagent to promote the direct condensation between carboxylic acids and alcohols or amines to provide esters, macrocyclic lactones, amides, as well as peptides without racemization. The regeneration of iodosodilactone (1) can also be readily achieved. The intermediate acyloxyphosphonium ion C from the activation of a carboxylic acid

  高价碘（III）试剂在促进羧酸与醇或胺之间的直接缩合以提供酯，大环内酯，酰胺以及未经消旋化作用的肽方面起着新颖的作用，可促进羧酸与醇或胺之间的直接缩合。碘代二内酯（1）的再生也可以容易地实现。据认为，来自羧酸活化的中间体酰氧基phosph离子C参与了本酯化反应。
• Stereochemical enzymatic synthesis of menthyl esters
  作者：N. R. Zemlyanskaya、A. A. Abdukarimova、Z. A. Adilova、Kh. M. Makhkamov

  DOI：10.1007/bf00629851

  日期：——
• Scandium triflate catalyzed ester synthesis using primary amides
  作者：Benjamin N. Atkinson、Jonathan M.J. Williams

  DOI：10.1016/j.tetlet.2014.10.124

  日期：2014.12

  A scandium triflate (ScOTf)(3) catalyzed methodology has been developed to synthesize esters from primary amides. Various primary and secondary aliphatic alcohols have been shown to react in n-heptane with a range of primary amides for 24 h. (C) 2014 The Authors. Published by Elsevier Ltd.
• Quantitative analyses of biochemical kinetic resolution of enantiomers. 2. Enzyme-catalyzed esterifications in water-organic solvent biphasic systems
  作者：Ching Shih Chen、Shih Hsiung Wu、Gary Girdaukas、Charles J. Sih

  DOI：10.1021/ja00243a040

  日期：1987.4