(S,E)-ethyl 3-hydroxy-5-phenylpent-4-enoate | 118918-32-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (S,E)-ethyl 3-hydroxy-5-phenylpent-4-enoate
• 英文别名: ethyl (E,3S)-3-hydroxy-5-phenylpent-4-enoate
• CAS: 118918-32-4
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: GKJRUOHBIQZQNO-IDVQTMNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 4-diethoxyphosphoryl-3-oxobutanoate 在 正丁基锂 、 ketoreductase 130 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， 反应 26.5h， 生成 (S,E)-ethyl 3-hydroxy-5-phenylpent-4-enoate
  参考文献：
  名称：

  Stereoselective synthesis of aryl γ,δ-unsaturated β-hydroxyesters by ketoreductases

  摘要：

  The biocatalytic reduction of aryl gamma,delta-unsaturated-beta-ketoesters was evaluated utilizing 24 different commercially available ketoreductases. In all cases, both (R) and (S)-enantiomers of gamma,delta-unsaturated beta-hydroxyesters were synthesized by one or more ketoreductases in excellent optical purity and yields. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.09.003

文献信息

• Heterogeneous versus Homogeneous Copper(II) Catalysis in Enantioselective Conjugate-Addition Reactions of Boron in Water
  作者：Taku Kitanosono、Pengyu Xu、Shū Kobayashi

  DOI：10.1002/asia.201300997

  日期：2014.1

  reported for the conjugate addition of boron. Heterogeneous cat. 1 also gave high yields and enantioselectivities with some substrates and also gave the highest TOF (43 200 h−1) for an asymmetric conjugate‐addition reaction of boron. In addition, the catalyst systems were also applicable to the conjugate addition of boron to α,β,γ,δ‐unsaturated carbonyl compounds, although such reactions have previously

  我们已经开发了Cu II催化的硼在水中与α，β-不饱和羰基化合物和α，β，γ，δ-不饱和羰基化合物的对映体共轭加成反应。与先前报道的需要有机溶剂的Cu I催化相反，发现手性Cu II催化在水中有效地进行。已经开发了三种催化剂体系：催化剂。1：具有手性配体L 1的Cu（OH）2；猫。2：具有配体L1的Cu（OH）2和乙酸；和猫。3：具有配体L1的Cu（OAc）2。而猫。1是异构系统，猫。2和猫。3是同质系统。我们测试了27种α，β-不饱和羰基化合物和α，β-不饱和腈化合物，包括无环和环状α，β-不饱和酮，无环和环状β，β-二取代的烯酮，无环和环状α，β-不饱和酯（包括其β，β-二取代形式）和无环α，β-不饱和酰胺（包括其β，β-二取代形式）。我们找到那只猫。2和猫。图3显示了几乎所有底物的高产率和对映选择性。值得注意的是，没有报道过能以高收率和高对映选择性耐受所有这些底物的催化剂。异类猫。1
• Asymmetric Reformatsky Reaction of Aldehydes Catalyzed by Novel <font>β</font>-Amino Alcohols and Zinc Complexes
  作者：Yan Li、Bin He

  DOI：10.1080/00397911.2013.879898

  日期：2014.7.3

  tridentate ligands has been applied to an asymmetric Reformatsky reaction of aldehydes with ethyl iodoacetate in the presence of ZnMe2. This novel catalytic system produced the desired β-hydroxyl esters with moderate to good enantioselectivities (up to 81% ee) and yields for many aldehydes, including aromatic, heteroaromatic, conjugated, and aliphatic aldehydes. GRAPHICAL ABSTRACT

  摘要 一系列衍生自 (1R, 2S)-2-amino-1,2-diphenylethanol 的 β-氨基醇和取代的水杨醛作为新型手性三齿配体已应用于醛与碘乙酸乙酯的不对称 Reformatsky 反应。 ZnMe2。这种新型催化系统产生了所需的 β-羟基酯，具有中等到良好的对映选择性（高达 81% ee），并且可以产生许多醛，包括芳香醛、杂芳香醛、共轭醛和脂肪醛。图形概要
• SYNTHETIC METHODS AND COMPOUNDS RELATED THERETO
  申请人：University Of Alaska Fairbanks

  公开号：US20150184206A1

  公开（公告）日：2015-07-02

  Disclosed herein are synthetic methods and compounds related to the compounds that are useful as or in the production of biologically active compounds. Stereoselective and stereospecific synthetic methods are disclosed to produce compounds, such as, for example, γ,δ-unsaturated-β-hydroxyesters and aminated derivatives thereof, at high yields with desired stereochemistry. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本文公开了与合成生物活性化合物有关的合成方法和化合物。公开了立体选择性和立体特异性合成方法，以高收率和所需立体化学合成化合物，例如γ，δ-不饱和-β-羟基酯及其氨基衍生物。本摘要旨在作为特定领域搜索的扫描工具，并不意味着限制本发明。
• Catalytic Enantioselective Reformatsky Reaction of Alkyl Iodoacetate with Aldehydes Catalyzed by Chiral Schiff Base
  作者：Takanori Tanaka、Masahiko Hayashi

  DOI：10.1246/cl.2008.1298

  日期：2008.12.5

  The catalytic enantioselective Reformatsky reaction with aldehydes catalyzed by chiral Schiff base 1 in the presence of Me2Zn under Ar–O2 atmosphere was achieved (up to 72% ee). This process provid...

  在Ar-O2 气氛下，在Me2Zn 存在下，由手性Schiff 碱1 催化的醛类催化对映选择性Reformatsky 反应得以实现（高达72% ee）。这个过程提供...
• Stereochemical preference of Candida parapsilosis ATCC 7330 mediated deracemization: E- versus Z-aryl secondary alcohols
  作者：Thangavelu Saravanan、Rajendran Selvakumar、Mukesh Doble、Anju Chadha

  DOI：10.1016/j.tetasy.2012.09.014

  日期：2012.10

  The stereochemical preference of the biocatalyst, Candida parapsilosis ATCC 7330, was investigated with respect to the E/Z configuration in the deracemization and the asymmetric reduction of aryl secondary alcohols and prochiral ketones, respectively. The biocatalyst preferred the E-isomers over Z-isomers as substrates as evidenced from the experimental results of > 99% ee and up to 86% isolated yield for E-secondary alcohols. The synthesis of enantiomerically pure E-4-phenylbut-3-ene-1,2-diol (ee > 99%, isolated yield 86%) by whole cell mediated deracemization is reported here for the first time. The geometric preference of the enzymes was confirmed by using the cell free extract of this biocatalyst. Mechanistic insights using in silico studies showed that the E-isomers when located in the active site are favourably placed with respect to the catalytic triad (Ser-Tyr-Lys) for hydride transfer from NADPH. (C) 2012 Elsevier Ltd. All rights reserved.