(-)-8-phenylmenthyl (2S)-2-hydroxy-4-pentenoate | 108794-01-0

• 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: (-)-8-phenylmenthyl (2S)-2-hydroxy-4-pentenoate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (2S)-2-hydroxypent-4-enoate
• CAS: 108794-01-0
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: CTDYISXJJBJSFO-OQIJWPOYSA-N

物化性质

• 沸点：
  429.3±25.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-8-phenylmenthyl (2S)-2-hydroxy-4-pentenoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以85%的产率得到(S)-2-hydroxypent-4-enoic acid
  参考文献：
  名称：

  Stereoselective intramolecular cyclopropanations: Enantioselective syntheses of 1α,25-dihydroxyvitamin D3 A-ring precursors

  摘要：

  Two efficient enantioselective syntheses of an A-ring precursor to 1 alpha,25-dihydroxyvitamin D-3 have been developed. The key step in these sequences involves the stereoselective cyclopropanation of a chiral gamma-alkoxy-alpha-diazo-beta-keto ester. In one sequence, the 1 alpha-hydroxy group was introduced in the first step by a diastereoselective ene reaction and in the other sequence by use of (S)-malic acid as starting material. Both routes eliminate the need for a SeO2 oxidation.

  DOI：

  10.1016/0040-4039(95)00284-j
• 作为产物：
  描述：

  长叶薄荷酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 10.0h， 生成 (-)-8-phenylmenthyl (2S)-2-hydroxy-4-pentenoate
  参考文献：
  名称：

  涉及手性酯烯醇酯末端的不对称 [2,3]-Wittig 重排。赤型-α-羟基-β-烷基羧酸衍生物的手性合成

  摘要：

  源自 (-)-8-苯基薄荷醇的 (E-2-链烯氧基) 乙酸酯的标题重排已显示出相应的 3-烷基-2-羟基-4-戊烯酸酯，具有极高水平的非对映面选择(95–97% de) 以及高红细胞选择性 (90–93%)。

  DOI：

  10.1246/cl.1987.69

文献信息

• Trifluoromethane sulphonic acid: a Brönsted acid catalyst for the addition of allyltributylstannanes to carbonyl compounds in water
  作者：Teck-Peng Loh、Jia Xu

  DOI：10.1016/s0040-4039(99)00122-7

  日期：1999.3

  Trifluoromethane sulphonic acid catalyses the addition of allyltributylstannane to carbonyl compounds in water to give the corresponding homoallylic alcohols in high yields.

  三氟甲烷磺酸催化将烯丙基三丁基锡烷加到水中的羰基化合物中，从而以高收率得到相应的均烯丙基醇。
• Enantioselective synthesis of unsaturated α-hydroxy acids
  作者：Jacqueline A. Macritchie、Alan Silcock、Christine L. Willis

  DOI：10.1016/s0957-4166(97)00571-5

  日期：1997.12

  (S)- and (R)-2-Hydroxyhex-5-enoic acid and (S)- and (R)-2-hydroxyhept-6-enoic acid were prepared in excellent yields and enantiomeric excesses (>99% ee) from the corresponding α-keto esters by the enzyme catalysed hydrolysis of the ester and reduction of the ketone in a single pot process. The enantioselective synthesis of (S)-2-hydroxypent-4-enoic acid was achieved via reaction of the reagent derived

  （S）和（R）-2-羟基己5-烯酸以及（S）-和（R）-2-羟基庚6-烯酸以优异的收率和对映体过量（> 99％ee）制备酶催化酯的水解并在单锅法中还原酮，从而生成相应的α-酮酯。（S）-2-羟基戊-4-烯酸的对映选择性合成是通过使烯丙基溴和铟金属衍生的试剂与水合草酸8-苯基薄荷基乙二酸酯的水合物反应而实现的。
• Asymmetric induction in the ene reaction of glyoxylate esters of 8-phenylmenthol
  作者：James K. Whitesell、Apurba Bhattacharya、Charles M. Buchanan、H.H. Chen、Don Deyo、Dustin James、Chi-Ling Liu、Mark A. Minton

  DOI：10.1016/s0040-4020(01)90590-3

  日期：1986.1

  Bhattacharya, D.A. Aguilar and K. Henke, J. Chem. Soc. Chem. Commun. 989 (1982)) a highly efficient and effective method for the control of absolute stereochemistry through asymmetric induction in the ene reaction the chiral glyoxylate 1 with alkenes. We now have accumulated sufficient information on this process in terms of both its mechanistic details as well as its scope and applicability to a variety

  我们最近进行了交流（JK Whitesell，A。Bhattacharya，DA Aguilar和K. Henke，J。Chem。Soc。Chem。Commun。989（1982）），是一种通过非对称诱导控制绝对立体化学的高效方法。烯使手性乙醛酸酯1与烯烃反应。现在，我们就此过程的机理细节，范围和适用于各种情况的适用性等方面积累了足够的信息，以确保对这些反应进行更完整的介绍。
• Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide
  作者：Katarzyna Kiegiel、Tomasz Bałakier、Piotr Kwiatkowski、Janusz Jurczak

  DOI：10.1016/j.tetasy.2004.10.025

  日期：2004.12

  The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide 13 is presented. (C) 2004 Elsevier Ltd. All rights reserved.
• Asymmetric [2,3]-Wittig Rearrangement Involving a Chiral Ester Enolate Terminus. A Chiral Synthesis of<i>erythro</i>-α-Hydroxy-β-alkyl Carboxylic Acid Derivatives
  作者：Osamu Takahashi、Koichi Mikami、Takeshi Nakai

  DOI：10.1246/cl.1987.69

  日期：1987.1.5

  The title rearrangement of the (E-2-alkenyloxy)acetic esters derived from (−)-8-phenylmenthol has been shown to afford the corresponding 3-alkyl-2-hydroxy-4-pentenoic ester with an extremely high level of diastereoface selection (95–97% de) along with a high erythro selectivity (90–93%).

  源自 (-)-8-苯基薄荷醇的 (E-2-链烯氧基) 乙酸酯的标题重排已显示出相应的 3-烷基-2-羟基-4-戊烯酸酯，具有极高水平的非对映面选择(95–97% de) 以及高红细胞选择性 (90–93%)。