(E)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-3-butenoic acid | 86017-93-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-3-butenoic acid
• 英文别名: (E)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)but-3-enoic acid；((E)-4-methoxy-benzylidene)-succinic acid-1-methyl ester；((E)-4-Methoxy-benzyliden)-bernsteinsaeure-1-methylester；2-(4-methoxybenzylidene)succinic acid 1-methyl ester；(3E)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)but-3-enoic acid；(E)-3-methoxycarbonyl-4-(4-methoxyphenyl)but-3-enoic acid
• CAS: 86017-93-8
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: JCZVRPGUXODGAO-JXMROGBWSA-N

物化性质

• 熔点：
  117-118 °C(Solv: hexane (110-54-3); chloroform (67-66-3))
• 沸点：
  432.7±40.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-3-butenoic acid 在 palladium on activated charcoal 氢气 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 甲醇 为溶剂， 反应 11.0h， 生成 methyl 6-methoxy-4-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
  参考文献：
  名称：

  Kinetic resolution of 3-hydroxymethylbenzocycloalkanols by selective asymmetric hydrogen-transfer oxidation

  摘要：

  Kinetic resolution of 3-hydroxymethylbenzocycloalkanols was performed by selective asymmetric hydrogen-transfer oxidation using the Ru(II)-(S,S)-TsDPEN catalyst. Thus, several 3-hydroxymethyl-1-tetralols 7a-d afforded (1R,3R)-3-hydroxymethyl-1-tetralols (1R,3R)-7a-d and (S)-3-hydroxymethyl-1-tetralones (S)-9a-d, and 3-hydroxymethyl-1-indanol 7e gave (1R,3S)3-hydroxymethyl-1-indanol (1R,3S)-7e and (R)-3-hydroxymethyl-1-indanone (R)-9e, with high enantioselectivities. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.016
• 作为产物：
  描述：

  seqtrans-p-Methoxybenzyliden-bernsteinsaeure 在 乙酰氯 作用下， 反应 6.0h， 生成 (E)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-3-butenoic acid
  参考文献：
  名称：

  Awad, William I.; Kandile, Nadia G.; Wassef, Wasfy N., Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 3, p. 405 - 410

  摘要：

  DOI：

文献信息

• 2-piperazinone-1-acetic acid derivatives and their use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06242600B1

  公开（公告）日：2001-06-05

  The present invention provides compounds and medicines effective for prophylaxis and therapy of various diseases by controlling or inhibiting cell-adhesion. Especially, the compounds of this invention inhibit platelet aggregation action without remarkable elongation of hemorrhagic period and can be used as a safe and long-acting antithrombotic drug as compared with known substances showing the same activity. Compounds of this invention are piperazinones of the formula: wherein the ring A is a basic heterocyclic group; the ring B is a nitrogen containing heterocyclic group or a cyclic hydrocarbon group; Y is CH2; R1 is H, OH, NH2 or an hydrocarbon group which may be bound through CO, S, SO or SO2; R2 is H or a hydrocarbon group; R3 is an optionally esterified or amidated carboxyl group; and D is a lower alkyl group substituted with an optionally esterified carboxyl group; or a salt thereof.

  本发明提供了通过控制或抑制细胞粘附来预防和治疗各种疾病的化合物和药物。特别是，本发明的化合物抑制血小板聚集作用，而不会显著延长出血期，并且与显示相同活性的已知物质相比，可以作为安全且长效的抗血栓药物使用。 本发明的化合物是以下式的哌嗪酮： 其中环A是一种碱性杂环基团；环B是含氮杂环基团或环烃基团；Y是CH2；R1是H、OH、NH2或可通过CO、S、SO或SO2结合的烃基团；R2是H或烃基团；R3是可选择酯化或酰胺化的羧基团；D是取代有可选择酯化羧基团的低碳基团；或其盐。
• Synthesis of Versatile Building Blocks through Asymmetric Hydrogenation of Functionalized Itaconic Acid Mono‐Esters
  作者：Koen F. W. Hekking、Laurent Lefort、André H. M. de Vries、Floris L. van Delft、Hans E. Schoemaker、Johannes G. de Vries、Floris P. J. T. Rutjes

  DOI：10.1002/adsc.200700307

  日期：2008.1.4

  The rhodium-catalyzed asymmetric hydrogenation of several β-substituted itaconic acid monoesters, using a library of monodentate phosphoramidite and phosphite ligands is described. Two β-alkyl-substituted substrates were readily hydrogenated by the rhodium complex Rh(COD)2BF4 in combination with (S)-PipPhos as a ligand resulting in ees of 99 %. In contrast, the corresponding more hindered β-aryl-substituted

  描述了使用单齿亚磷酰胺和亚磷酸酯配体的文库，铑催化几种β-取代衣康酸单酯的不对称氢化。两个β-烷基取代的底物很容易被铑配合物Rh（COD）2 BF 4与作为配体的（S）-PipPhos结合而氢化，结果ee值为99％。相反，在这些条件下，相应的受阻更大的β-芳基取代的底物没有表现出可接受的对映选择性。但是，使用48元配体文库导致针对这些底物鉴定了几种合适的配体，从而导致ees为89–99％。所得的光学活性琥珀酸衍生物是潜在的用于更精细化合物的构建基块，因为能够区分分子两侧的羧酸和酯基。
• Catalytic Asymmetric Alkynylation and Arylation of Aldehydes by an H ₈ ‐Binaphthyl‐Based Amino Alcohol Ligand
  作者：Jiwu Ruan、Gui Lu、Lijing Xu、Yue‐Ming Li、Albert S. C. Chan

  DOI：10.1002/adsc.200700215

  日期：2008.1.4

  prepared in situ) to aldehydes, yielding the corresponding optically active propargylic alcohols and diarylmethanols in high yields and good to excellent enantioselectivities. For the asymmetric arylation reaction, one catalyst (1Ra,2S,3R)-2 can afford both enantiomers of many pharmaceutically interesting diarylmethanols by a proper combination of various arylzinc reagents and aldehydes.

  合成了一种新型的手性H 8 -1,1'-联萘基氨基醇配体（1 R a，2 S，3 R）-2，并用于有机锌的直接亲核加成（炔基锌和芳基锌原位制备）生成醛类，以高收率和良好至优异的对映选择性产生相应的旋光炔丙醇和二芳基甲醇。对于不对称芳基化反应，一种催化剂（1 R a，2 S，3 R）-2 通过适当地组合各种芳基锌试剂和醛，可以提供许多药学上感兴趣的二芳基甲醇的两种对映异构体。
• Stereocontrolled Synthesis of (+)-Plagiogyrin A
  作者：Yunlong Shi、Joshua G. Pierce

  DOI：10.1021/acs.orglett.6b02629

  日期：2016.10.21

  was first isolated from the fronds of Plagiogyria matsumureana. Structurally, it features an α-ketoaldehyde functional group in its hemiacetal form, fused in a cis-substituted lactone ring. We have successfully synthesized the skeleton of this natural product by employing a stereocontrolled aldol reaction followed by the installation of the α-ketoaldehyde moiety derived from the mild oxidation of an

  Plagiogyrin A（1）首先从Plagiogyria matsumureana的叶中分离出来。在结构上，它具有半缩醛形式的α-酮醛官能团，稠合在顺式取代的内酯环上。我们已经成功地通过立体控制的羟醛反应合成了该天然产物的骨架，随后安装了由α-二氮酮的轻度氧化衍生而来的α-酮醛部分。最后，无水酸性条件释放出被保护的二醇，并提供所需的环化半缩醛。
• Enantioselective Synthesis of the Tetracyclic Core of Platensimycin
  作者：Hisanaka Ito、Yohei Ueda、Kayoko Iwahashi、Kazuo Iguchi

  DOI：10.1055/s-0030-1260002

  日期：2011.5

  A concise preparative method for the tetracyclic core of platensimycin in an optically active form was developed through a nine-step sequence from p-anisaldehyde without the use of protecting groups. antibiotics - enantioselective hydrogenation - iodoetherification - formal synthesis

  通过九步法从对茴香醛中不使用保护基团开发了一种光学活性形式的盘菌素四环核的简明制备方法。 抗生素-对映选择性氢化-碘醚化-正式合成