(+)-menthyl butyrate | 115114-96-0

• 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: (+)-menthyl butyrate
• 英文别名: [(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl] butanoate
• CAS: 115114-96-0
• 化学式: C₁₄H₂₆O₂
• 分子量: 226.359
• InChiKey: PHCRRQSBYWJFBQ-XQQFMLRXSA-N

物化性质

• 沸点：
  262.7±8.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

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：

  (+)-menthyl butyrate 、 tert-butyl N-[3-[tert-butyl(diphenyl)silyl]oxy-1-methoxypropyl]carbamate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  在将α-甲氧基氨基甲酸酯原位生成的N-甲氧基羰基亚胺中加入烯酸酯阴离子的非对映选择性

  摘要：

  研究了向α-甲氧基氨基甲酸酯原位生成的N-甲氧基羰基亚胺中添加酮或酯的烯醇酸根阴离子的非对映选择性。

  DOI：

  10.1016/s0040-4039(00)72728-6
• 作为产物：
  描述：

  D-薄荷醇 、 丁酰氯 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以20.91 g的产率得到(+)-menthyl butyrate
  参考文献：
  名称：

  d-薄荷醇脂肪酸酯衍生物及其应用和制备方法

  摘要：

  本发明属于医药技术领域，涉及一种d‑薄荷醇脂肪酸酯衍生物及其应用和制备方法。所述的d‑萜品醇脂肪酸酯是由d‑薄荷醇与直链脂肪酸经酯化反应而得到的。方法是首先脂肪酸与氯化亚砜反应制备酰氯，然后酰氯与d‑薄荷醇反应制备成酯而得到的。d‑薄荷醇酯作为促透剂应用于贴剂、巴布剂、软膏剂、凝胶剂、喷雾剂、搽剂外用制剂，从而提高药物特别是手性药物对映体的经皮吸收量，是一种很好的经皮吸收促透剂，具有广阔的应用前景。

  公开号：

  CN106631789A

文献信息

• 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
• TiCl4 promoted menthyl ester chiral auxiliary mediated synthesis of chiral syn-β-amino esters and applications of a representative syn-β-amino ester
  作者：Mariappan Periasamy、Subramaniapillai Selva Ganesan、Surisetti Suresh

  DOI：10.1016/j.tetasy.2010.02.010

  日期：2010.3

  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.
• Enzymatic Production of l-Menthol by a High Substrate Concentration Tolerable Esterase from Newly Isolated Bacillus subtilis ECU0554
  作者：Gao-Wei Zheng、Hui-Lei Yu、Jian-Dong Zhang、Jian-He Xu

  DOI：10.1002/adsc.200800412

  日期：2009.2

  Abstractmagnified imageEnzymatic preparation of l‐menthol has been attracting much attention in the flavor and fragrance industry. A new ideal strain, Bacillus subtilis ECU0554, which exhibited high hydrolytic activity and excellent enantioselectivity towards l‐menthyl ester, has been successfully isolated from soil samples through enrichment culture and identified as Bacillus subtilis by 16S rDNA gene sequencing. The esterase extracted from B. subtilis ECU0554 (BSE) showed the best catalytic properties (E>200) for dl‐menthyl acetate among the five menthyl esters examined. Enantioselective hydrolysis of 100 mM dl‐menthyl acetate at 30°C and pH 7.0, using crude BSE as biocatalyst and 10% ethanol (v/v) as cosolvent, resulted in 49.0% conversion (3 h) and 98.0% ee for the l‐menthol produced, which were much better than those using commercial enzymes tested. Moreover, BSE exhibited strong tolerance against high substrate concentration (up to 500 mM), and the concentration of l‐menthol produced could reach as high as 182 mM, and more importantly, the optical purity of l‐menthol produced was kept above 97% ee, which were not found in previous reports. These results imply that BSE is a potentially promising biocatalyst for the large‐scale enzymatic preparation of l‐menthol. Using this excellent biocatalyst, the enzymatic production of l‐menthol will become a mild, efficient, inexpensive and easy‐to‐use “green chemistry” methodology.
• SHONO, TATSUYA;KISE, NAOKI;SANDA, FUMIO;OHI, SATORI;YOSHIOKA, KEN, TETRAHEDRON LETT., 30,(1989) N0, C. 1253-1256
  作者：SHONO, TATSUYA、KISE, NAOKI、SANDA, FUMIO、OHI, SATORI、YOSHIOKA, KEN

  DOI：——

  日期：——