ethyl 2-(3,4-dichlorophenyl)acrylate | 390406-26-5

• 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: ethyl 2-(3,4-dichlorophenyl)acrylate
• 英文别名: ethyl 2-(3,4-dichlorophenyl)prop-2-enoate
• CAS: 390406-26-5
• 化学式: C₁₁H₁₀Cl₂O₂
• 分子量: 245.105
• InChiKey: HJDCIJHAMOIIGY-UHFFFAOYSA-N

物化性质

• 沸点：
  348.0±37.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3,4-dichlorophenyl)acrylate 在 锂硼氢 、 三乙胺 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-[[4-[[2-(3,4-dichlorophenyl)-3-(propan-2-ylamino)propyl]amino]phenyl]methyl]-2,2-dimethylpropanamide
  参考文献：
  名称：

  Discovery and initial structure–Activity relationships of trisubstituted ureas as thrombin receptor (PAR-1) antagonists

  摘要：

  Thrombin is the most potent agonist of platelet activation, and its effects are predominantly mediated by platelet thrombin receptors. Therefore, antagonists of the thrombin receptor have potential utility for the treatment of thrombotic disorders. Screening of combinatorial libraries revealed 2 to be a potent antagonist of the thrombin receptor. Modifications of this structure produced 11k, which inhibits thrombin receptor stimulated secretion and aggregation of platelets. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00538-8
• 作为产物：
  描述：

  聚合甲醛 、 3,4-二氯苯基乙酸乙酯 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 生成 ethyl 2-(3,4-dichlorophenyl)acrylate
  参考文献：
  名称：

  钯催化的C（sp 2）–H键的直接分子间甲硅烷基化立体选择性合成Z-乙烯基硅烷

  摘要：

  据报道，通过使用乙硅烷作为硅源，借助易于去除的双齿引导基团，可以有效，方便地催化钯催化的C（sp 2）-H键直接分子间甲硅烷基化。该策略为Z-乙烯基硅烷的独家合成提供了区域和立体选择性的方案，具有合理至优异的收率和良好的官能团相容性。分离的palladacycle中间体的甲硅烷基化揭示了Z-立体选择性途径。此外，该方法的实用性和有效性通过克规模的实验和甲硅烷基化产物的进一步功能化进行了说明。

  DOI：

  10.1021/acs.orglett.7b02486

文献信息

• Nitrogen-containing heterocyclic compound and use thereof
  申请人：Ikeura Yoshinori

  公开号：US20090156572A1

  公开（公告）日：2009-06-18

  The present invention relates to a compound represented by the formula wherein ring A is a nitrogen-containing heterocycle optionally further having substituent(s), ring B is an aromatic ring optionally having substituent(s), ring C is a cyclic group optionally having substituent(s), R 1 is a hydrogen atom, a hydrocarbon group optionally having substituent(s), an acyl group, a heterocyclic group optionally having substituent(s) or an amino group optionally having substituent(s), R 2 is an optionally halogenated C 1-6 alkyl group, m and n are each an integer of 0 to 5, m+n is an integer of 2 to 5, and is a single bond or a double bond, or a salt thereof and the like. Since the compound has a superior tachykinin receptor antagonistic action, and is useful as an agent for the prophylaxis or treatment of various diseases such as lower urinary tract diseases, gastrointestinal diseases, central nervous system diseases and the like.

  本发明涉及一种由下式表示的化合物：其中环A是含氮杂环，可选择地进一步具有取代基，环B是芳香环，可选择地具有取代基，环C是环状基团，可选择地具有取代基，R1是氢原子，一个碳氢基团，可选择地具有取代基，酰基，一个杂环基团，可选择地具有取代基或一个氨基团，可选择地具有取代基，R2是可选择卤代的C1-6烷基基团，m和n分别是0到5的整数，m+n是2到5的整数，是单键或双键，或其盐等。由于该化合物具有优越的催吐肽受体拮抗作用，可用作预防或治疗多种疾病的药物，如下尿道疾病、胃肠道疾病、中枢神经系统疾病等。
• A 1,3,2‐Diazaphospholene‐Catalyzed Reductive Claisen Rearrangement
  作者：John H. Reed、Pavel A. Donets、Solène Miaskiewicz、Nicolai Cramer

  DOI：10.1002/anie.201904411

  日期：2019.6.24

  catalysts for very mild reductive Claisen rearrangements. The method is tolerant towards a wide variety of functional groups and operates at ambient temperature. Besides being enantiospecific for substrates with existing stereogenic centers, the diastereoselectivity can be switched by varying solvents and DAP catalysts. The reaction kinetics show direct rearrangements of O‐bound phospholene enolates

  1,3,2-二氮杂磷烯（DAP）是新兴的一类有机氢化物。在这项工作中，我们利用它们作为非常温和的还原性克莱森重排的有效催化剂。该方法可耐受多种官能团，并在环境温度下运行。除了对具有现有立体异构中心的底物是对映体特异性的以外，还可以通过改变溶剂和DAP催化剂来改变非对映选择性。反应动力学表明O结合的磷烯烯酸酯直接重排，并为催化对映选择性反应提供了原理证明。
• Photoinduced umpolung addition of carbonyl compounds with α,β-unsaturated esters enables the polysubstituted γ-lactone formation
  作者：Jia-Yi Gu、Wei Zhang、Seth R. Jackson、Yan-Hong He、Zhi Guan

  DOI：10.1039/d0cc05306f

  日期：——

  herein report the photoinduced intermolecular umpolung addition of aromatic ketones/aldehydes with α,β-unsaturated esters via ketyl radical intermediates. Following an intramolecular transesterification, a variety of γ-lactone derivatives are readily accessed. Mechanistic investigations demonstrate the significant role of Hantzsch ester, which serves both as the electron and proton donor.

  本文我们报告的光诱导分子间极性转换添加具有α，β不饱和酯的芳族酮/醛的通过羰自由基中间体。分子内酯交换后，很容易获得各种γ-内酯衍生物。机理研究表明，汉茨酯具有重要的作用，它既可以作为电子也可以作为质子供体。
• Enantioselective [3 + 2] Cycloaddition of Allenes to Acrylates Catalyzed by Dipeptide-Derived Phosphines: Facile Creation of Functionalized Cyclopentenes Containing Quaternary Stereogenic Centers
  作者：Xiaoyu Han、Youqing Wang、Fangrui Zhong、Yixin Lu

  DOI：10.1021/ja1106282

  日期：2011.2.16

  A new family of dipeptide-based chiral phosphines was designed and prepared. D-Thr-L-tert-Leu-derived catalyst 4c promoted [3 + 2] cycloaddition of allenoates to α-substituted acrylates in a regiospecific and stereoselective manner, furnishing functionalized cyclopentenes with quaternary stereogenic centers in high yields and with excellent enantioselectivities.

  设计并制备了一个新的基于二肽的手性膦家族。D-Thr-L-tert-Leu 衍生的催化剂 4c 以区域专一性和立体选择性的方式促进了烯丙酸酯的 [3 + 2] 环加成反应到 α-取代的丙烯酸酯，以高产率和优异的对映选择性提供具有四元立体中心的官能化环戊烯。
• α-Arylsulfonyloxyacrylates: attractive <i>O</i>-centered electrophiles for synthesis of α-substituted acrylates <i>via</i> Pd-catalysed Suzuki reactions
  作者：Zhongya Zhang、Li Zhang、Linge Huai、Zhentao Wang、Yewen Fang

  DOI：10.1039/d3ra00401e

  日期：——

  We herein report α-arylsulfonyloxyacrylates as a kind of useful and attractive O-centered electrophiles for Suzuki cross-coupling reactions. A range of α-(hetero)aryl substituted acrylates has been prepared via the palladium-catalysed C–C cross-coupling reactions between potassium (hetero)aryltrifluoroborates and α-arylsulfonyloxyacrylates. Moreover, α-arylsulfonyloxyacrylate could also react with

  我们在此报道了 α-芳基磺酰氧基丙烯酸酯作为一种有用且有吸引力的以 O为中心的亲电子试剂，用于 Suzuki 交叉偶联反应。通过钯催化的（杂）芳基三氟硼酸钾和 α-芳基磺酰氧基丙烯酸酯之间的钯催化 C-C 交叉偶联反应制备了一系列 α-（杂）芳基取代的丙烯酸酯。此外，α-芳基磺酰氧基丙烯酸酯还可以与B-alkyl-9-BBN反应生成α-烷基取代的丙烯酸酯。通过合成维甲酸X受体-选择性维甲酸的中间体的制备证明了这种新方法的合成应用。这些基于 Suzuki 反应的方案具有广泛的底物范围、通用性和温和的反应条件。