(2R)-(E)-2-Hydroxy-4-phenylbut-3-enoic acid ethyl ester | 676477-93-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (2R)-(E)-2-Hydroxy-4-phenylbut-3-enoic acid ethyl ester
• 英文别名: (R)-trans-ethyl 2-hydroxy-4-phenylbut-3-enoate；ethyl (R,E)-2-hydroxy-4-phenylbut-3-enoate；(R)-ethyl 2-hydroxy-4-phenylbut-3-enoate；ethyl (E)-2-hydroxy-4-phenylbut-3-enoate；ethyl (E,2R)-2-hydroxy-4-phenylbut-3-enoate
• CAS: 676477-93-3
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: VKJBHXYAEPBVRG-ANYFNZRUSA-N

物化性质

• 沸点：
  347.0±30.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (2R)-(E)-2-Hydroxy-4-phenylbut-3-enoic acid ethyl ester 在 palladium diacetate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 22.0h， 生成 (2E,4S)-ethyl 4-(2-naphthylamino)-4-phenylbut-2-enoate
  参考文献：
  名称：

  利用钯催化的烯丙基氨基甲酸酯重排反应合成对映体富集的γ-氨基-α，β-不饱和酯，可直接用于形式上的[3 + 2]环加成反应

  摘要：

  通过利用钯催化在烯丙基位置具有酯部分的烯丙基氨基甲酸酯的对苯甲酸丰富的脱羧重排反应，开发了对映体富集的γ-氨基-α，β-不饱和酯的有效合成方法。通过使用黄磷作为催化剂的优良配体，反应以高收率和高手性转移进行。该产品直接在Brønsted碱催化下与异氰酸甲苯酯进行正式的[3 + 2]环加成反应，从而得到对映体富集的β，γ-二氨基酸衍生的咪唑烷基-2-酮作为多功能手性构建基。

  DOI：

  10.1021/acs.orglett.7b00471
• 作为产物：
  描述：

  1,1-Diethoxy-2-hydroxy-4-phenylbut-3-enyl-1-(diphenylphosphine oxide) 在 甲基磺酰胺 、 potassium tert-butylate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 0.25h， 生成 (2R)-(E)-2-Hydroxy-4-phenylbut-3-enoic acid ethyl ester
  参考文献：
  名称：

  A New Asymmetric Formylation of Aldehydes

  摘要：

  DOI：

  10.1002/anie.199702531

文献信息

• Regio- and Stereospecific <i>C</i>- and <i>O</i>-Allylation of Phenols via π-Allyl Pd Complexes Derived from Allylic Ester Carbonates
  作者：Christopher A. Discolo、Alexander G. Graves、Donald R. Deardorff

  DOI：10.1021/acs.joc.6b02608

  日期：2017.1.20

  for the C- and O-allylation of phenols via a common π-allyl Pd complex. While O-allylation of phenols by this method is a well-recognized reaction of general utility, the associated para-selective C-allylation reaction is still in its infancy. Cationic π-allyl Pd intermediates, derived from allylic ester carbonates and palladium(0) catalyst, were found to undergo the Friedel–Crafts-type para-selective

  通过共同的π-烯丙基Pd络合物，已开发出两种互补的策略用于苯酚的C-和O-烯丙基化。尽管通过这种方法进行的酚的O-烯丙基化是公认的通用反应，但是相关的对位选择性C-烯丙基化反应仍处于起步阶段。发现衍生自烯丙基碳酸酯和钯（0）催化剂的阳离子π-烯丙基Pd中间体经历了9种不同酚的Friedel-Crafts型对选择性C-烯丙基化反应。这两个C-和O-在金属催化的区域和立体有向取代性1,3-移位后，可以得到高至极好收率的烯丙基化产物。还确定了控制进入任一烯丙基化产品的条件。最后，对两种烯丙基化产物之间建立的平衡的研究表明，O-烯丙基化的化合物是动力学产物，而C-烯丙基化的化合物是热力学产物。
• Cobalt-Catalyzed Enantioselective Vinylation of Activated Ketones and Imines
  作者：Yuan Huang、Rui-Zhi Huang、Yu Zhao

  DOI：10.1021/jacs.6b02372

  日期：2016.5.25

  We present here an unprecedented cobalt-catalyzed enantioselective vinylation of α-ketoesters, isatins, and imines to deliver a range of synthetically useful allylic alcohols and amines in high enantiopurity. This method employs commercially available and easy to handle catalysts and reagents and exhibits a high degree of practicality. The efficiency, selectivity, and operational simplicity of this

  我们在此展示了一种前所未有的钴催化的 α-酮酯、靛红和亚胺的对映选择性乙烯基化，以提供一系列具有高对映纯度的合成有用的烯丙醇和胺。该方法采用市售且易于处理的催化剂和试剂，具有很高的实用性。该催化系统的效率、选择性和操作简单性加上底物的通用性使该方法成为有机合成中的宝贵工具。
• Asymmetric Nucleophilic Acylation of Aldehydes via 1,1-Heterodisubstituted Alkenes
  作者：Holger Monenschein、Gerald Dräger、Alexander Jung、Andreas Kirschning

  DOI：10.1002/(sici)1521-3765(19990802)5:8<2270::aid-chem2270>3.0.co;2-l

  日期：1999.8.2

  Aldehydes are asymmetrically acylated by a two step sequence that is initiated by a homologation step to 1,1-heterodisubstituted alkenes followed by asymmetric dihydroxylation. Thus, ketene O,S-acetals are efficiently prepared from aldehydes by a Peterson olefination with lithiated methoxy-phenylthiotrimethylsilyl methane 14 as the C-1 source. Although they are dihydroxylated with the Sharpless catalyst with moderate to good enantioselectivity (62-80% ee), the process is not efficient owing to the low chemical yields of the desired alpha-hydroxy methyl esters (7-37%). Use of the corresponding sulfoxide 24 or sulfon 25 led to an improved chemical yield of alpha-hydroxy methyl ester 19, but the stereoselectivity was diminished. In contrast, intermediate ketene O,O-acetals are prepared by a Horner-Wittig reaction with phosphine oxide 31 and are dihydroxylated both with good chemical and stereochemical yield. The concept is applicable to aromatic, aliphatic, and chiral aldehydes. For example, this short sequence allows exclusive and independent preparation of both diastereomeric heptoses 69a and 69b.
• Asymmetric reduction of alkyl 2-oxo-4-arylbutanoates and -but-3-enoates by Candida parapsilosis ATCC 7330: assignment of the absolute configuration of ethyl 2-hydroxy-4-(p-methylphenyl)but-3-enoate by 1H NMR
  作者：Baburaj Baskar、N. Ganesh Pandian、Kuttikode Priya、Anju Chadha

  DOI：10.1016/j.tetasy.2004.11.002

  日期：2004.12

  Enantioselective bioreduction of alkyl 2-oxo-4-arylbutanoates and 2-oxo-4-arylbut-3-enoates mediated by Candida parapsilosis ATCC 7330 resulted in the formation of the corresponding (S)-2-hydroxy compounds in high enantiomeric excesses (93-99%) and good isolated yields (58-71%). The absolute configuration of enantiomerically pure ethyl 2-hydroxy-4-(p-methylphenyl)but-3-enoate obtained by the reduction of the corresponding keto ester was assigned by H-1 NMR using Mosher's method. (C) 2004 Elsevier Ltd. All rights reserved.
• Stereoselective reduction of C=X by a chiral 1,4-dihydropyridine (NADH-MIMIC) in a self-immolative process
  作者：A.I. Meyers、Jack D. Brown

  DOI：10.1016/s0040-4039(00)80827-8

  日期：1988.1