(R)-2-phenyl-4-pentenoic acid | 1575-70-8

• 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: (R)-2-phenyl-4-pentenoic acid
• 英文别名: (R)-2-phenylpent-4-enoic acid；(2R)-phenylpent-4-enoic acid；(2S)-phenylpent-4-enoic acid；2-phenylpent-4-enoic acid；(R)-2-phenyl-pent-4-enoic acid；(R)-2-Phenyl-pent-4-ensaeure；(2R)-2-phenylpent-4-enoic acid
• CAS: 1575-70-8；21490-59-5；94086-47-2；110658-35-0
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: IQZLXJUYCRPXRG-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-phenyl-4-pentenoic acid 在 potassium permanganate 、 正己烷 、 氢溴酸 、 sodium carbonate 作用下， 生成 (R)-(-)-2-phenylglutaric acid
  参考文献：
  名称：

  Westman, Arkiv foer Kemi, 1957, vol. 11, p. 431,435

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯基戊-4-烯酸 生成 (R)-2-phenyl-4-pentenoic acid
  参考文献：
  名称：

  Veldstra; van de Westeringh, Recueil des Travaux Chimiques des Pays-Bas, 1951, vol. 70, p. 1127,1131

  摘要：

  DOI：

文献信息

• Uniting C1-Ammonium Enolates and Transition Metal Electrophiles via Cooperative Catalysis: The Direct Asymmetric α-Allylation of Aryl Acetic Acid Esters
  作者：Kevin J. Schwarz、Jessica L. Amos、J. Cullen Klein、Dung T. Do、Thomas N. Snaddon

  DOI：10.1021/jacs.6b01694

  日期：2016.4.27

  constitutes a significant challenge in the area of asymmetric catalysis, particularly where the configurational integrity of the products is problematic. Through the unprecedented merger of two independent, yet complementary, catalysis events it has been possible to facilitate the direct asymmetric α-allylation of readily available aryl acetic acid esters. Since enantioselection is determined by the nucleophile

  无环酯的直接、催化、不对称 α-官能化在不对称催化领域构成了重大挑战，特别是在产品的构型完整性存在问题的情况下。通过两个独立但互补的催化事件的前所未有的合并，有可能促进容易获得的芳基乙酸酯的直接不对称α-烯丙基化。由于对映选择是由亲核试剂决定的，这种协同催化的概念方法构成了无环酯直接催化不对称α-官能化的潜在通用解决方案。
• An efficient route to 1,3-amino hydroxyl system via electrophilic lactonization of 2-amino-4-pentenoic acid derivatives. Stereoselective synthesis of (−)-bulgecinine
  作者：Yasufumi Ohfune、Keiko Hori、Masahiro Sakaitani

  DOI：10.1016/s0040-4039(00)85403-9

  日期：1986.1

  Several γ-hydroxy-α-amino acid systems were prepared stereoselectively from 2-amino-4-pentenoic acid derivatives using electrophilic lactonization. This strategy was applied to the synthesis of a highly functionalized proline analogue, (−)-bulgecinine (4).

  使用亲电子内酯化作用，由2-氨基-4-戊烯酸衍生物立体选择性地制备了几种γ-羟基-α-氨基酸系统。该策略被用于合成高度功能化的脯氨酸类似物（-）-bulgecinine（4）。
• Highly Enantioselective Direct Alkylation of Arylacetic Acids with Chiral Lithium Amides as Traceless Auxiliaries
  作者：Craig E. Stivala、Armen Zakarian

  DOI：10.1021/ja205107x

  日期：2011.8.10

  A direct, highly enantioselective alkylation of arylacetic acids via enediolates using a readily available chiral lithium amide as a stereodirecting reagent has been developed. This approach circumvents the traditional attachment and removal of chiral auxiliaries used currently for this type of transformation. The protocol is operationally simple, and the chiral reagent is readily recoverable.

  已经开发出使用容易获得的手性氨基锂作为立体定向试剂通过烯二醇对芳基乙酸进行直接、高度对映选择性的烷基化。这种方法绕过了目前用于此类转化的手性助剂的传统附着和去除。该方案操作简单，手性试剂易于回收。
• Remarkable Electronic and Steric Effects in the Nitrile Biotransformations for the Preparation of Enantiopure Functionalized Carboxylic Acids and Amides:  Implication for an Unsaturated Carbon−Carbon Bond Binding Domain of the Amidase
  作者：Ming Gao、De-Xian Wang、Qi-Yu Zheng、Zhi-Tang Huang、Mei-Xiang Wang

  DOI：10.1021/jo070581b

  日期：2007.8.1

  various functionalized racemic nitriles catalyzed by Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole-cell catalyst, were studied. While the nitrile hydratase exhibits high catalytic efficiency but very low enantioselectivity against almost all nitrile substrates examined, the amidase is very sensitive toward the structure of the amides. The release of the steric crowdedness

  红球菌催化各种功能化外消旋腈的生物转化研究了含腈水合酶/酰胺酶的微生物全细胞催化剂AJ270。尽管腈水合酶显示出高的催化效率，但对几乎所有所检测的腈底物的对映选择性都非常低，但酰胺酶对酰胺的结构非常敏感。围绕基质立体中心的空间拥挤的释放以及向基质中引入不饱和碳-碳键导致反应速率的显着加速和对映选择性的显着提高。腈的生物转化提供了独特的，高产的合成路线，可合成被烯丙基，炔丙基，烯基或乙烯基官能化的高度对映体纯的羧酸和酰胺。H-喹啉-2-酮衍生物。
• Enantioselective synthesis of levomilnacipran
  作者：Julien Alliot、Edmond Gravel、Florence Pillon、David-Alexandre Buisson、Marc Nicolas、Eric Doris

  DOI：10.1039/c2cc33743f

  日期：——

  A novel approach for the asymmetric synthesis of the active (1S,2R)-enantiomer of the antidepressant milnacipran is reported. The two stereogenic centers borne by the cyclopropane ring were sequentially installed starting from phenylacetic acid.

  报告采用一种新方法不对称地合成了抗抑郁药物米那西普兰的活性 (1S,2R)-对映体。从苯乙酸开始，依次安装环丙烷环上的两个立体中心。