Methyl 2-hydroxy-3-phenyl-3-butenoate | 91828-63-6

• 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: Methyl 2-hydroxy-3-phenyl-3-butenoate
• 英文别名: methyl 3-phenyl-2-hydroxy-3-butenoate；2-Hydroxy-3-phenyl-but-3-enoic acid methyl ester；methyl 2-hydroxy-3-phenylbut-3-enoate
• CAS: 91828-63-6
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: VRHSFVNLFOJOQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2-hydroxy-3-phenyl-3-butenoate 在 sodium hydroxide 、 氢气 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 4-苯基-二氢-呋喃-2,3-二酮
  参考文献：
  名称：

  Design, synthesis, and evaluation of postulated transient intermediate and substrate analogues as inhibitors of 4-hydroxyphenylpyruvate dioxygenase

  摘要：

  An epoxybenzoquinone, 4-hydroxyphenoxypropionic acid, and 2-hydroxy-3-phenyl-3-butenoic acid derivatives have been designed, synthesized, and evaluated for in vitro inhibition activity against 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) from pig liver by the spectrophotometric enol-borate method. The biological data demonstrated that neither epoxybenzoquinone ester nor 2-hydroxy-3-phenyl-3-butenoic acid is an inhibitor of 4-HPPD. The most potent 4-HPPD inhibitor tested was 3-hydroxy-4-phenyl-2(5H)-furanone with an IC50 value of 0.5 muM, which may serve as a lead compound for further design of more potent 4-HPPD inhibitors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00291-3
• 作为产物：
  描述：

  3-methyl-3-phenyl-oxiranecarboxylic acid methyl ester 生成 Methyl 2-hydroxy-3-phenyl-3-butenoate
  参考文献：
  名称：

  Catalyst and method for isomerization

  摘要：

  一个异构化催化剂，其基本上由以下公式表示的盐或复盐组成：[ML.sub.m ].sup.n+ [Y].sub.n.sup.-（I），其中M是周期表中IB、IIA、IIB或VIII族的金属，L是配体，Y是布朗斯特酸的共轭碱，m为0、1、2、3或4，n为1、2或3。

  公开号：

  US04621150A1

文献信息

• Catalyst and method for isomerization
  申请人：Sagami Chemical Research Center

  公开号：US04621150A1

  公开（公告）日：1986-11-04

  A catalyst for isomerization consisting essentially of a salt or complex salt represented by the formula: [ML.sub.m ].sup.n+ [Y].sub.n.sup.- (I) where M is a metal of Group IB, IIA, IIB or VIII of the periodic table, L is a ligand, Y is a conjugated base of a Bronsted acid, m is 0, 1, 2, 3 or 4 and n is 1, 2 or 3.

  一个异构化催化剂，其基本上由以下公式表示的盐或复盐组成：[ML.sub.m ].sup.n+ [Y].sub.n.sup.-（I），其中M是周期表中IB、IIA、IIB或VIII族的金属，L是配体，Y是布朗斯特酸的共轭碱，m为0、1、2、3或4，n为1、2或3。
• Lewis Acid-Catalyzed Hetero-Diels–Alder Reactions of Methyl 2-Oxo-3-alkenoates with Alkenes
  作者：Akira Sera、Meguru Ohara、Hiroaki Yamada、Emiko Egashira、Naohiro Ueda、Jun-ichiro Setsune

  DOI：10.1246/bcsj.67.1912

  日期：1994.7

  cycloadditions of 4-substituted methyl 2-oxo-3-butenoates and -3-pentenoates with alkenes took place with high regio- and stereoselectivities to afford substituted 6-methoxycarbonyl-3,4-dihydro-2H-pyrans in good to moderate yields. None of the ene products were produced. Similar reactions of methyl 3-phenyl-2-oxo-3-butenoate with alkenes afforded both the corresponding 3,4-dihydro-2H-pyrans and a dimeric cycloadduct

  路易斯酸催化 4-取代的 2-氧代-3-丁烯酸甲酯和-3-戊烯酸甲酯与烯烃的环加成反应具有高区域选择性和立体选择性，得到良好的取代 6-甲氧羰基-3,4-二氢-2H-吡喃到适度的产量。没有生产烯产品。3-苯基-2-氧代-3-丁烯酸甲酯与烯烃的类似反应得到相应的 3,4-二氢-2H-吡喃和二烯组分的二聚环加合物。目前的逆电子需求环加成反应的区域选择性和立体选择性表明反应是通过协调一致的外向过渡态进行的。
• Selective Isomerization of Glycidates and Their Analogues with Triphenylsilyl Perchlorate or Electrogenerated Acid
  作者：Tsutomu Inokuchi、Masahiko Kusumoto、Sigeaki Matsumoto、Hiroyuki Okada、Sigeru Torii

  DOI：10.1246/cl.1991.2009

  日期：1991.11

  Isomerization of glycidic esters and nitriles to the corresponding 2-hydroxy-3-alkenoates and their nitrile derivatives occurred on treatment with triphenylsilyl perchlorate or electrogenerated acid (EG acid). The cyanohydrin moiety of the nitriles 4 was transformed to a formyl group, giving the corresponding enals on treatment with weak base.

  用三苯基甲硅烷基高氯酸酯或电生酸（EG酸）处理时，缩水甘油酯和腈异构化为相应的2-羟基-3-烯酸酯及其腈衍生物。腈4的氰醇部分转化为甲酰基，用弱碱处理得到相应的烯醛。
• OXAZOLIDINEDIONE DERIVATIVES, PROCESS FOR THEIR PREPARATION, AND HERBICIDES CONTAINING THE SAME
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP0241559B1

  公开（公告）日：1991-10-30
• HIRAI, KENJI;FUTIKAMI, TAKAMASA;MURATA, ATSUKO;HIROSE, HIROAKI;YOKOTA, MA+
  作者：HIRAI, KENJI、FUTIKAMI, TAKAMASA、MURATA, ATSUKO、HIROSE, HIROAKI、YOKOTA, MA+

  DOI：——

  日期：——