(2S,3E)-4-phenylbut-3-ene-1,2-diol | 229648-88-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (2S,3E)-4-phenylbut-3-ene-1,2-diol
• 英文别名: (S)-(E)-4-phenylbut-3-ene-1,2-diol；(2S,E)-4-phenylbut-3-ene-1,2-diol；(2S)-4-phenyl-but-3-ene-1,2-diol；(S,E)-4-phenylbut-3-ene-1,2-diol；(2S,3E)-4-phenyl-1,2-butenediol；(E,2S)-4-phenylbut-3-ene-1,2-diol
• CAS: 229648-88-8
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: NIKBSMYNKTUHIF-FGEFZZPRSA-N

物化性质

• 熔点：
  55-57 °C
• 沸点：
  350.3±30.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3E)-4-phenylbut-3-ene-1,2-diol 在 咪唑 、 二异丁基氢化铝 、 二正丁基氧化锡 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 (3R,4E)-3-(tert-butyldimethylsilanyloxy)-5-phenylpent-4-enal
  参考文献：
  名称：

  合成抗癌活性goniothalamin的两种简单且替代的方法

  摘要：

  为构建 (R)-goniothalamin（一种天然抗癌剂）开发了两种替代且直接的途径。第一种方法从 (R)-缩水甘油开始，包括炔烃和亚砜 Julia-Lythgoe 烯化的立体选择性（部分）还原作为关键步骤。第二种方法涉及从 2,3-O-异亚丙基-D-甘油醛合成 (R)goniothalamin，其中部分还原腈和 Still-Gennari 立体选择性烯化作为关键步骤。这两种标准有机反应顺序简单的方法可用于有机化学二、三年级课程。

  DOI：

  10.24820/ark.5550190.p010.461
• 作为产物：
  描述：

  Benzoic acid (E)-(S)-2-acetoxy-4-phenyl-but-3-enyl ester 在 甲醇 、 sodium methylate 作用下， 反应 24.0h， 生成 (2S,3E)-4-phenylbut-3-ene-1,2-diol
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiomerically pure alkene 1,2-diols and glycosides thereof

  摘要：

  The kinetic resolution of racemic 2-O-acylated 3-butene-1,2-diol and 1-O-acylated 3-butene-1,2-diol derivatives by enzymatic saponification and enzymatic esterification, respectively, is investigated with several lipases and esterases. The resulting partially blocked enantiomers are glycosylated with glycosyl halides and trichloroacetimidates, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00051-2

文献信息

• A Concise Enantioselective Strategy to (+)-(R)-Goniothalamin and (+)-(R)-Goniothalamin Oxide by Employing Hydrolytic Kinetic Resolution and Ring-Closing Metathesis as Key Steps
  作者：D. Bose、A. V. Reddy、Bingi Srikanth

  DOI：10.1055/s-2008-1067175

  日期：2008.8

  An efficient and general strategy to (R)-goniothalamin and (R)-goniothalamin oxide is described by using Jacobsen’s hydrolytic­ kinetic resolution of racemic epoxide and ring-closing metathesis (RCM) as key steps, which provided a rapid access to these natural products that display a fascinating array of biological activity. (R)-Goniothalamin oxide was prepared in high yield and diastereomeric excess under various epoxidation conditions.

  一种高效且通用的策略用于合成 (R)- goniothalamin 和 (R)- goniothalamin 氧化物，关键步骤包括 Jacobsen 的水解动力学分辨法和环闭合 метатезис（RCM），该策略提供了快速获得这些具有迷人生物活性的天然产物的途径。在不同的环氧化条件下，成功制备了高产率和对映体过量的 (R)-goniothalamin 氧化物。
• A Short and General Approach to the Synthesis of Styryllactones:(+)-Goniodiol, its Acetates and β-Trifluoromethyl Derivative, (+)-7-<i>epi</i>-Goniodiol and (+)-9-Deoxygoniopypyrone
  作者：Guo-Qiang Lin、Jian Chen、Zhi-Min Wang、Han-Quan Liu

  DOI：10.1055/s-2002-32977

  日期：——

  (+)-Goniodiol, its acetates and β-trifluoromethyl derivative, (+)-7-epi-Goniodiol and (+)-9-deoxygoniopypyrone, the representatives of styryllactones have been synthesized in a short and general way. The key steps involve the regioselective asymmetric dihydroxylation and the palladium-catalyzed cross-coupling of cyclic allylic carbonate with vinyltributylstannane.

  (+)-Goniodiol 及其醋酸盐和δ-三氟甲基衍生物、(+)-7-epi-Goniodiol 和 (+)-9-deoxygoniopypyrone 是苯乙烯内酯的代表，这些化合物已通过简短而通用的方法合成。关键步骤包括环状烯丙基碳酸酯与乙烯基三丁基锡的区域选择性不对称二羟基化和钯催化交叉耦合。
• Regio- and enantio-selective oxidation of diols by Candida parapsilosis ATCC 7330
  作者：Thakkellapati Sivakumari、Anju Chadha

  DOI：10.1039/c4ra08146c

  日期：——

  Optically pure (S)-diols and their corresponding hydroxy ketones were prepared via regio- and enantio-selective oxidation of the corresponding diols using whole cells of Candida parapsilosis ATCC 7330.

  通过使用Candida parapsilosis ATCC 7330的整细胞，对相应的二醇进行区域选择性和对映选择性氧化，制备了光学纯的(S)-二醇及其相应的羟基酮。
• An enantiocontrolled synthesis of the masked taxol C-13 side chain, oxazoline carboxylic acid
  作者：Sung Ho Kang、Cheol Min Kim、Joo-Hack Youn

  DOI：10.1016/s0040-4039(99)00577-8

  日期：1999.4

  Oxazoline carboxylic acid 6 as the taxol side chain precursor has been efficiently synthesized via the intramolecular iodoamidation of allylic trichloroacetimidate derived from trans-olefinic diol 1.

  通过紫杉醇侧链前体的恶唑啉羧酸6通过分子内的碘化从反式链烯二醇1衍生的烯丙基三氯乙亚氨酸酯被有效地合成。
• 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.