(-)-menthyl butyrate | 6070-14-0

• 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: (-)-menthyl butyrate
• 英文别名: menthyl butanoate；((1R)-menthyl)-butyrate；Buttersaeure-((1R)-menthylester)；(1R)-O-Butyryl-menthol；((1R)-Menthyl)-butyrat；menthyl butyrate；l-Menthyl butyrate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] butanoate
• CAS: 6070-14-0
• 化学式: C₁₄H₂₆O₂
• 分子量: 226.359
• InChiKey: PHCRRQSBYWJFBQ-FRRDWIJNSA-N

物化性质

• LogP：
  5.201 (est)
• 物理描述：
  clear colorless liquid/tropical cool aroma
• 溶解度：
  Practically insoluble to insoluble
• 密度：
  0.912-0.915
• 折光率：
  1.445-1.450

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  N-(3-methylbenzylidene)-1-phenylmethanamine 、 (-)-menthyl butyrate 在 四氯化钛 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.67h， 以71%的产率得到(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R)-2-[(R)-1-benzylamino-1-(3-methylphenyl)methyl]butanoate
  参考文献：
  名称：

  TiCl4 promoted menthyl ester chiral auxiliary mediated synthesis of chiral syn-β-amino esters and applications of a representative syn-β-amino ester

  摘要：

  beta-Amino esters were obtained in up to 78% yield with 72:28-96:4 diastereomeric ratios by the reaction of the chiral titanium enolate of menthyl esters, prepared using the TiCl4/Et3N reagent system with prochiral imines. A representative syn-beta-amino ester derivative has been used for the resolution of racemic mandelic acid to obtain a sample with >99% ee in a single step. A representative syn-beta-amino ester was converted to the corresponding N-deprotected amino ester using the Pd-C/HCOOH reagent system, and then to the corresponding beta-amino acid using the glacial CH3COOH/HCl reagent system, and to the corresponding beta-lactam derivative with partial epimerization by the reaction using C2H5MgBr. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.010
• 作为产物：
  描述：

  L-薄荷醇 、 丁酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到(-)-menthyl butyrate
  参考文献：
  名称：

  TiCl4 promoted menthyl ester chiral auxiliary mediated synthesis of chiral syn-β-amino esters and applications of a representative syn-β-amino ester

  摘要：

  beta-Amino esters were obtained in up to 78% yield with 72:28-96:4 diastereomeric ratios by the reaction of the chiral titanium enolate of menthyl esters, prepared using the TiCl4/Et3N reagent system with prochiral imines. A representative syn-beta-amino ester derivative has been used for the resolution of racemic mandelic acid to obtain a sample with >99% ee in a single step. A representative syn-beta-amino ester was converted to the corresponding N-deprotected amino ester using the Pd-C/HCOOH reagent system, and then to the corresponding beta-amino acid using the glacial CH3COOH/HCl reagent system, and to the corresponding beta-lactam derivative with partial epimerization by the reaction using C2H5MgBr. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.010

文献信息

• AN ENANTIOMER DIFFERENTIATING REACTION OF<i>p</i>-TOLYLSULFINYLCARBANION WITH (−)-MENTHYL CARBOXYLATES
  作者：Norio Kunieda、Hiroaki Motoki、Masayoshi Kinoshita

  DOI：10.1246/cl.1978.713

  日期：1978.7.5

  Treatment of (−)-menthyl carboxylates(2) with 2 equiv of p-tolylsulfinylcarbanion(1) afforded the corresponding optically active β-keto sulfoxides(3) together with optically active methyl p-tolyl sulfoxide. The enantiomeric purity and the predominant configuration of the products were discussed.

  用 2 当量的对甲苯基亚磺酰基碳负离子 (1) 处理 (-)-薄荷基羧酸盐 (2)，得到相应的旋光 β-酮亚砜 (3) 和旋光甲基对甲苯亚砜。讨论了产物的对映体纯度和主要构型。
• Candida rugosa lipase: Enantioselectivity enhancements in organic solvents
  作者：Rose A. Persichetti、Jim J. Lalonde、Chandrika P. Govardhan、Nazer K. Khalaf、Alexey L. Margolin

  DOI：10.1016/0040-4039(96)01430-x

  日期：1996.9

  Chiral resolutions of carboxylic acids (1-3) and alcohol (4) were carried out through esterification or transesterification in organic solvents using cross-linked enzyme crystals (CLEC(R)) of Candida rugosa lipase (CRL). Comparison of these results with those of elude CRL reveal significant differences. As was seen in resolution through hydrolysis,(1) a marked improvement in enantioselectivity is realized with the CLEC. Additionally, the stability afforded the enzyme in CLEC form leads to a higher activity in organic solvent. Copyright (C) 1996 Elsevier Science Ltd
• Facile synthesis of chiral O-alkyl enol ethers
  作者：Florence Charbonnier、Albert Moyano、Andrew E. Greene

  DOI：10.1021/jo00387a038

  日期：1987.5
• Biocatalytic enantiomeric resolution of l-menthol from an eight isomeric menthol mixture through transesterification
  作者：D. Brady、S. Reddy、B. Mboniswa、L.H. Steenkamp、A.L. Rousseau、C.J. Parkinson、J. Chaplin、R.K. Mitra、T. Moutlana、S.F. Marais、N.S. Gardiner

  DOI：10.1016/j.molcatb.2011.10.011

  日期：2012.3

  The four diastereomers of menthol and their enantiomers, namely DL-menthol, DL-neomenthol, DL-neoisomenthol and DL-isomenthol, were synthesised by the hydrogenation of thymol to yield an eight isomer liquid menthol. A suitably selective lipase was sought to preferentially esterify L-menthol in organic solvent, hence simplifying separation from the diasteromeric mix through distillation. From an initial screen a commercial Pseudomonas fluorescens lipase (Amano AK) was selected, and vinyl acetate was chosen as a suitable irreversible acyl donor for transesterification. The reaction reagent ratios were optimised, and an enantiomeric excess (ee) of L-menthol of greater than 95% was reproducibly achievable at a conversion of 30% DL-menthol (0.68 M) at <= 50 degrees C. On the basis of the composition of liquid menthol the reaction had a diastereomeric excess (de) of 82%. The enzyme was recycled 150 times in 5 ml batch reactions using liquid menthol and achieving an overall yield of 184.3 g DL-menthol/g commercial enzyme preparation. The by-product acetic acid, formed by hydrolysis of menthyl acetate, was found to cause a high degree of enzyme inactivation.The resolution reaction was scaled up 400 fold to 2 L and the enzyme recycled 38 times with an average conversion of the available L-menthol of 59% and a volumetric productivity of 1.2 g/L/h. (C) 2011 Elsevier B.V. All rights reserved.
• NAGAO, Y.;HAGIWARA, Y.;TOHJO, T.;HASEGAWA, Y.;OCHIAI, M.;SHIRO, M., J. ORG. CHEM., 53,(1988) N5, C. 5983-5986
  作者：NAGAO, Y.、HAGIWARA, Y.、TOHJO, T.、HASEGAWA, Y.、OCHIAI, M.、SHIRO, M.

  DOI：——

  日期：——

表征谱图