ethyl 2-((3-chlorophenyl)(hydroxy)methyl)acrylate

• 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-chlorophenyl)(hydroxy)methyl)acrylate
• 英文别名: Ethyl 2-[(3-chlorophenyl)-hydroxymethyl]prop-2-enoate
• 化学式: C₁₂H₁₃ClO₃
• mdl: MFCD11130457
• 分子量: 240.686
• InChiKey: PFQZKPPCYZEHIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  ethyl 2-((3-chlorophenyl)(hydroxy)methyl)acrylate 在 硫酸 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-2-Bromomethyl-3-(3-chloro-phenyl)-acrylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of thio-heterocyclic analogues from Baylis–Hillman bromides as potent cyclooxygenase-2 inhibitors

  摘要：

  A series of thio-substituted pyrimidine, benzoxazole, benzothiazole and triazole analogues were synthesized from Baylis-Hillman bromides in a clean and efficient way. The synthesized twenty new compounds were subjected to in vitro COX-1 and COX-2 inhibitory activity. Majority of compounds found to be highly selective COX-2 inhibitor. Seven compounds (16e, 16f, 16k, 16l, 16m, 16r and 16s) displayed anti-inflammatory activity at micromolar concentrations with IC50 values for COX-2 inhibition ranging from 2.93 to 5.34 mu M compared to reference drug whose IC50 is 2.66 mu M. All these seven compounds had very little COX-1 inhibition property and thus are suitable candidates for anti-inflammatory drugs with less gastrointestinal side effect. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.073
• 作为产物：
  描述：

  3-氯苯甲醛 、 丙烯酸乙酯 在 三乙烯二胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 ethyl 2-((3-chlorophenyl)(hydroxy)methyl)acrylate
  参考文献：
  名称：

  通过意外的碳-碳键裂解将肼插入N'-烷基苯甲酰肼的路线。

  摘要：

  衍生自Morita-Baylis-Hillman加合物的丙烯酸苯甲酰酯与肼反应中的偶然碳-碳键裂解，生成了新的N'，N'-二取代苯并酰肼。该反应的特征在于两个碳-氮键的区域选择性形成，并且与一系列丙烯酸酯和肼反应良好。简短的机械研究暗示周期性半胱氨酸可能是中间产物。

  DOI：

  10.1021/acs.orglett.9b02657

文献信息

• Fe(III)-Catalyzed Hydroallylation of Unactivated Alkenes with Morita–Baylis–Hillman Adducts
  作者：Jifeng Qi、Jing Zheng、Sunliang Cui

  DOI：10.1021/acs.orglett.8b00108

  日期：2018.3.2

  An Fe(III)-catalyzed hydroallylation of unactivated alkenes with Morita–Baylis–Hillman adducts via an Fe-catalyzed process is described. A variety of alkenes, including mono-, di-, and trisubstituted alkenes, could all smoothly convert to structural diversified cinnamates in this protocol. Interestingly, when the hydroxyl-containing alkenes were used, various lactones could be rapidly assembled. Moreover

  描述了铁（III）催化未活化的烯烃与森田-贝利斯-希尔曼加合物通过铁催化的过程的加氢反应。在此方案中，各种烯烃（包括单，二和三取代的烯烃）都可以顺利转化为结构多样化的肉桂酸酯。有趣的是，当使用含羟基的烯烃时，可以迅速组装各种内酯。而且，该协议可以应用于天然产物的后期功能化。
• Methylsulfenylation of Electrophilic Carbon Atoms: Reaction Development, Scope, and Mechanism
  作者：Adriane A. Pereira、Amanda S. Pereira、Amanda C. de Mello、Arthur G. Carpanez、Bruno A. C. Horta、Giovanni W. Amarante

  DOI：10.1002/ejoc.201601613

  日期：2017.3.27

  An innovative methodology for methylsulfenylation of electrophilic carbons is presented. Cheaper and commercially available dimethylsulfoxide (DMSO) is now used as a source of -SCH3 group. Chalcone, dibenzylideneacetone (DBA) as well as Morita-Baylis-Hillman (MBH) adduct derivatives were successfully sulfenylated, giving the corresponding products with moderate to high isolated yields. Control experiments

  提出了一种用于亲电碳甲基亚磺酰化的创新方法。现在使用更便宜且可商购的二甲基亚砜 (DMSO) 作为 -SCH3 基团的来源。查尔酮、二亚苄基丙酮 (DBA) 以及 Morita-Baylis-Hillman (MBH) 加合物衍生物被成功地磺酰化，得到相应的产物，分离产率中等至高。对照实验和 DFT 计算揭示了 DMSO 过程的脱氧和硫中间体的亲核加成是整个机制中的关键步骤。
• Aromatic Spiroketal Bisphosphine Ligands: Palladium-Catalyzed Asymmetric Allylic Amination of Racemic Morita-Baylis-Hillman Adducts
  作者：Xiaoming Wang、Fanye Meng、Yan Wang、Zhaobin Han、Yong-Jun Chen、Li Liu、Zheng Wang、Kuiling Ding

  DOI：10.1002/anie.201204925

  日期：2012.9.10

  and enantioselectivity in the palladium‐catalyzed asymmetric allylic amination of racemic Morita–Baylis–Hillman adducts with aromatic amines. The methodology provides a facile and efficient synthesis of precursors for optically active β‐lactam derivatives, including the cholesterol drug Ezetimibe.

  显示主链：双（膦）配体1的螺骨架主链在外消旋的Morita-Baylis-Hillman加合物与芳族胺的钯催化的不对称烯丙基胺化反应中产生了良好的区域和对映选择性。该方法为光学活性β-内酰胺衍生物（包括胆固醇药物依泽替米贝）的前体提供了便捷，高效的合成方法。
• Electron-Donor–Acceptor Complex-Enabled Flow Methodology for the Hydrotrifluoromethylation of Unsaturated β-Keto Esters
  作者：Gabriel M. F. Batista、Pedro P. de Castro、Hélio F. Dos Santos、Kleber T. de Oliveira、Giovanni W. Amarante

  DOI：10.1021/acs.orglett.0c03187

  日期：2020.11.6

  (EDA) complex-enabled flow photochemical hydrotrifluoromethylation of unsaturated β-keto esters is described. The developed protocol has an easy experimental procedure and does not require the use of transition-metal-based photocatalysts, allowing the isolation of 14 new compounds in up to 86% yield. Control experiments and computational studies revealed that the reaction proceeds through a Michael-type

  描述了一种新型的电子给体-受体（EDA）络合物使不饱和β-酮酯流动光化学加氢三氟甲基化反应。所开发的方案具有简单的实验程序，不需要使用过渡金属基光催化剂，从而可以以高达86％的产率分离出14种新化合物。对照实验和计算研究表明，该反应通过三氟甲基的迈克尔型1,4-加成反应进行，随后是质子转移步骤。此外，该反应可放大至1mmol，并且最终产物可用于制备异恶唑酮和吡唑啉酮作为三氟取代的杂环。
• INDOLIZINONE BASED DERIVATIVES AS POTENTIAL PHOSPHODIESTERASE 3 (PDE3) INHIBITORS AND A PROCESS FOR THE PREPARATION THEREOF
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20140296530A1

  公开（公告）日：2014-10-02

  The present invention provides compounds of general formula A useful as potential phosphodiesterase3 (PDE3) inhibitory agents and a process for the preparation thereof. The derivatives of formula A can be employed as therapeutics in human and veterinary medicine, where they can be used, for example, for the treatment and prophylaxis of the following diseases: heart failure, dilated cardiomyopathy, platelet inhibitors, cancer and obstructive pulmonary diseases.

  本发明提供了一般式A的化合物，作为潜在的磷酸二酯酶3（PDE3）抑制剂，并提供了其制备方法。一般式A的衍生物可用作人类和兽医药学中的治疗剂，例如可用于治疗和预防以下疾病：心力衰竭、扩张型心肌病、血小板抑制剂、癌症和阻塞性肺部疾病。