(2S)-2-hydroxy-2-phenyl-4-pentenoic acid | 81037-04-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-hydroxy-2-phenyl-4-pentenoic acid
• 英文别名: (S)-2-Hydroxy-2-phenyl-4-pentenoic Acid；(S)(+)-α-allyl-mandelic acid；(2S)-2-hydroxy-2-phenylpent-4-enoic acid
• CAS: 81037-04-9
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: CYKFMWAISISCIE-NSHDSACASA-N

物化性质

• 熔点：
  133-134 °C(Solv: toluene (108-88-3))
• 沸点：
  362.3±37.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-hydroxy-2-phenyl-4-pentenoic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 以95%的产率得到(S)(+)-α-propyl-mandelic acid
  参考文献：
  名称：

  Pig-liver-esterase-catalyzed hydrolyses of racemic .alpha.-substituted .alpha.-hydroxy esters

  摘要：

  DOI：

  10.1021/jo00310a020
• 作为产物：
  描述：

  扁桃酸 在 盐酸 、 sodium hydroxide 、 KH₂PO₄ buffer 、 lithium diisopropyl amide 作用下， 以 乙醇 、 苯 为溶剂， 反应 8.0h， 生成 (2S)-2-hydroxy-2-phenyl-4-pentenoic acid
  参考文献：
  名称：

  Pig-liver-esterase-catalyzed hydrolyses of racemic .alpha.-substituted .alpha.-hydroxy esters

  摘要：

  DOI：

  10.1021/jo00310a020

文献信息

• Improved Robust Method for Preparing Optically Active 3-Alkyl-3-phenyl-1,4-dioxane-2,5-diones; A Promising New Chiral Template
  作者：Yoo Tanabe、Ryohei Nagase、Yuuki Iida、Mikiko Sugi、Tomonori Misaki

  DOI：10.1055/s-0028-1083211

  日期：2008.11

  A robust method for preparing (3S)-3-alkyl-3-phenyl-1,4-dioxane-2,5-diones was developed using an improved cyclocondensation reaction between (S)-α-alkylmandelic acids and 2-bromocarbonyl halides. Subtle differences in the reaction conditions, including separate additions of triethylamine, significantly increased the yield compared with Schollkopf's original method.

  使用改进的 (S)-α-烷基扁桃酸和 2-溴羰基卤化物之间的环缩合反应，开发了一种制备 (3S)-3-烷基-3-苯基-1,4-二恶烷-2,5-二酮的稳健方法。与 Schollkopf 的原始方法相比，反应条件的细微差异（包括单独添加三乙胺）显着提高了产率。
• PLE catalyzed hydrolyses of α-substituted α-hydroxy esters: The influence of the substituents.
  作者：Henk Moorlag、Richard M. Kellogg

  DOI：10.1016/s0957-4166(00)86125-x

  日期：1991.1

  The enzymatic hydrolyses of a variety of α-substituted mandelic and lactic esters using pig liver esterase (PLE) have been investigated. High to moderate enantioselectivity was found for various α-substituted mandelic esters, whereas PLE showed low to no enantioselectivity for α-substituted lactic esters. We observed that the enantioselectivity of PLE depends strongly on the length and nature of the

  已经研究了使用猪肝酯酶（PLE）酶促水解各种α-取代的扁桃酸酯和乳酸酯的方法。发现对各种α-取代的扁桃酸酯具有高到中等的对映选择性，而PLE对α-取代的乳酸酯显示出低至没有对映选择性。我们观察到，PLE的对映选择性很大程度上取决于α位置取代基的长度和性质。讨论了PLE的活动站点模型的一些后果。
• Isomannide and isosorbide as new chiral auxiliaries for the stereoselective synthesis of tertiary α-hydroxy acids
  作者：André Loupy、Daphné A Monteux

  DOI：10.1016/s0040-4020(02)00024-8

  日期：2002.2

  isosorbide are selectively protected to provide new chiral auxiliaries suitable for the preparation of enantiopure tertiary α-hydroxy acids. Diastereoselective additions of organozinc reagents on the derived phenylglyoxylates afford the desired α-hydroxy acids with 60–99% ee after saponification. Both absolute configurations of the α-hydroxy acids can be accessed, by adapted choice of either the starting

  异甘露糖醇和异山梨醇被选择性保护，以提供适用于制备对映纯叔α-羟基酸的新型手性助剂。在衍生的苯乙醛酸酯上非对映选择性地添加有机锌试剂，可在皂化后提供具有60-99％ee的所需α-羟基酸。的α羟基酸既绝对构型可以通过起始二醇或保护基团的选择适于进行访问。
• Asymmetric synthesis of tetrahydrofurans by diastereoselective [3+2] cycloaddition of allylsilanes with α-keto esters bearing an optically active cyclitol as a chiral auxiliary
  作者：Takahiko Akiyama、Takuya Yasusa、Keiichiro Ishikawa、Shoichiro Ozaki

  DOI：10.1016/s0040-4039(00)74417-0

  日期：1994.11

  Tin (IV) chloride mediated [3+2] cycloadditions of allylsilanes with optically active α-keto esters derived from L-quebrachitol afforded tetrahydrofuran derivatives via 1,2-silyl migration with high level of diastereoselectivity. Removal of the chiral auxiliary gave silyl-substituted tetrahydrofurans of excellent optical purity.

  氯化锡（IV）介导的烯丙基硅烷与衍生自L-邻苯二酚的光学活性α-酮酯的[3 + 2]环加成反应通过1,2-甲硅烷基迁移以高非对映选择性提供四氢呋喃衍生物。除去手性助剂得到具有优异光学纯度的甲硅烷基取代的四氢呋喃。
• Enantioselective [2,3]-Wittig Rearrangement of Carboxylic Acid Derived Enolates by Tetradentate Chiral Lithium Amide
  作者：Ryuichi Shirai、Kenji Yatsuzuka、Midori Kawasaki

  DOI：10.1055/a-2039-6352

  日期：——

  A chiral lithium amide mediated enantioselective [2,3]-Wittig rearrangement of carboxylic acid enolate has been developed. The reaction proceeds through the formation of a chiral mixed aggregate that shields one enantioface of enolate anion to give a highly functionalized chiral α-hydroxycarboxylic acid.

  摘要 开发了一种手性锂酰胺介导的羧酸对映体选择性 [2,3]-Wittig 重排反应。该反应通过形成手性混合聚集体来屏蔽烯酸根阴离子的一个对映面，从而得到高度官能化的手性α-羟基羧酸。