menthyl pentanoate | 64129-94-8

• 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: menthyl pentanoate
• 英文别名: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl pentanoate；(1R-(1alpha,2beta,5alpha))-5-Methyl-2-(1-methylethyl)cyclohexyl valerate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] pentanoate
• CAS: 64129-94-8
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: LCJPVSLESAPYMK-HZSPNIEDSA-N

物化性质

• 沸点：
  278.7±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)：
  5
• 重原子数：
  17
• 可旋转键数：
  6
• 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：

  1-碘己烷 、 menthyl pentanoate 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 生成 2-Propyl-octanoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
  参考文献：
  名称：

  Alkylation ofl- andd-Menthyl Pentanoate with (20S)-20-Iodomethyl-4α-methyl-5α-pregnane

  摘要：

  The alkylation of l- and d-menthyl valerate with n-hexyl iodide and with (20S)-20-iodomethyl-4 alpha-methyl-5 alpha-pregnane gave modest levels of diastereoselection. The chirality of the ester group favoured slight degree of selectivity. The chiral centers had limited impact on diastereoselectivity.

  DOI：

  10.1080/00397919608004775
• 作为产物：
  描述：

  L-薄荷醇 、 正戊酸 以 甲苯 为溶剂， 生成 menthyl pentanoate
  参考文献：
  名称：

  Candida rugosa lipase: Enantioselectivity enhancements in organic solvents

  摘要：

  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

  DOI：

  10.1016/0040-4039(96)01430-x

文献信息

• Defluorinative Multi‐Functionalization of Fluoroaryl Sulfoxides Enabled by Fluorine‐Assisted Temporary Dearomatization
  作者：Mengjie Hu、Yuchen Liang、Liying Ru、Sheng Ye、Lei Zhang、Xin Huang、Ming Bao、Lichun Kong、Bo Peng

  DOI：10.1002/anie.202306914

  日期：2023.9.4

  Owing to its unique physical properties, fluorine is often used to open up new reaction channels. In this report, we establish a cooperation of [5,5]‐rearrangement and fluorine‐assisted temporary dearomatization for arene multi‐functionalization. Specifically, the [5,5]‐rearrangement of fluoroaryl sulfoxides with β,γ‐unsaturated nitriles generates an intriguing dearomatized sulfonium species which is short‐lived but exhibits unusually high electrophilicity and thus can be instantly trapped by nucleophiles and dienes at a remarkably low temperature (−95 °C) to produce four types of valuable multi‐functionalized benzenes, respectively, involving appealing processes of defluorination, desulfurization, and sulfur shift. Mechanistic studies indicate that the use of fluorine on arenes not only circumvents the generally inevitable [3,3]‐rearrangement but also impedes the undesired rearomatization process, thus provides a precious space for constructing and elaborating the temporarily dearomatized fluorinated sulfonium species.

  摘要由于其独特的物理特性，氟经常被用来开辟新的反应途径。在本报告中，我们建立了[5,5]重排和氟辅助临时脱芳烃的合作关系，以实现炔的多功能化。具体来说，[5,5]-氟芳基硫醚与 β,γ-不饱和腈的重排反应会产生一种有趣的脱芳基锍物种，这种锍物种的寿命很短，但却表现出异常高的亲电性，因此可以在极低的温度（-95 °C）下被亲核剂和二烯瞬间捕获，分别生成四种有价值的多功能化苯，其中涉及脱氟、脱硫和硫转移等吸引人的过程。机理研究表明，在炔类化合物上使用氟，不仅可以规避一般不可避免的 [3,3]- 重排，还可以阻碍不受欢迎的重芳烃化过程，从而为构建和阐述暂时脱芳烃的氟化锍物种提供了宝贵的空间。
• 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
• Alkylation of<i>l</i>- and<i>d</i>-Menthyl Pentanoate with (20S)-20-Iodomethyl-4α-methyl-5α-pregnane
  作者：Ayhan S. Demir

  DOI：10.1080/00397919608004775

  日期：1996.12

  The alkylation of l- and d-menthyl valerate with n-hexyl iodide and with (20S)-20-iodomethyl-4 alpha-methyl-5 alpha-pregnane gave modest levels of diastereoselection. The chirality of the ester group favoured slight degree of selectivity. The chiral centers had limited impact on diastereoselectivity.