2-hydroxy-4-methoxycinnamic acid ethyl ester | 240113-82-0

• 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: 2-hydroxy-4-methoxycinnamic acid ethyl ester
• 英文别名: Ethyl 3-(2-hydroxy-4-methoxyphenyl)prop-2-enoate；ethyl 3-(2-hydroxy-4-methoxyphenyl)prop-2-enoate
• CAS: 240113-82-0
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: XFXBVFUUEWWMFT-UHFFFAOYSA-N

物化性质

• 沸点：
  384.7±27.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-4-methoxycinnamic acid ethyl ester 在 三乙基硅烷 、 palladium 10% on activated carbon 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 β-(2-Hydroxy-4-methoxy-phenyl)-propionsaeure
  参考文献：
  名称：

  钌催化的分子内芳烃C（sp 2）–H酰胺化反应合成3,4-Dihydroquinolin-2（1 H）-ones

  摘要：

  我们报道了[Ru（对-cymene）（l-脯氨酸）Cl]（[Ru1]）催化的1,4,2-二恶唑-5-酮环化反应形成二氢喹啉-2-酮，具有优异的产率和极好的区域选择性通过正式的分子内芳烃C（sp 2）–H酰胺化。2-和4-取代的芳基二恶唑酮的反应首先通过在芳烃位点上的亲电酰胺化的螺内酰胺化进行，该芳烃位点对取代基是对位的或邻位的。Hammett相关性研究表明，螺内酰胺化可能是由于对苯丙氨酸的亲电子亚硝基化合物攻击而发生的，其特征是-0.73的负ρ值。

  DOI：

  10.1021/acs.orglett.1c00781
• 作为产物：
  描述：

  2-羟基-4-甲氧基苯甲醛 、 乙氧甲酰基亚甲基三苯基膦 以 甲苯 为溶剂， 反应 3.0h， 生成 2-hydroxy-4-methoxycinnamic acid ethyl ester
  参考文献：
  名称：

  自由基诱导的 2-烷基 3-烯丙基反式-2,3-二氢苯并呋喃 (TADHBs) 的快速立体选择性合成

  摘要：

  摘要 对包含烯烃和环丙烷环境的自由基诱导的环丙基环断裂进行了彻底的研究。有趣的是，片段化引发了立体选择性合成 3-烯丙基反式-2,3-二氢苯并呋喃，收率令人印象深刻。反式二氢苯并呋喃是许多具有药用价值的分子的中心核心，本协议提供了对嵌入式分子结构的直接访问。图形概要

  DOI：

  10.1080/00397911.2017.1415357

文献信息

• Synthesis of Lactams via Ir-Catalyzed C–H Amidation Involving Ir-Nitrene Intermediates
  作者：Jitian Liu、Wenjing Ye、Shuojin Wang、Junrong Zheng、Weiping Tang、Xiaoxun Li

  DOI：10.1021/acs.joc.0c00157

  日期：2020.3.20

  We have developed a divergent strategy for the synthesis of five- and six-membered lactams via either an amidation of sp3 C-H bonds or electrophilic substitution of arenes via Ir-nitrene intermediates. With the employment of a readily available iridium catalyst in dichloromethane or hexafluoro-2-propanol, a wide range of lactams were synthesized in good to excellent yields with high selectivity.

  我们已经开发了一种通过sp3 CH键的酰胺化或Ir-nitrene中间体亲电取代芳烃来合成五元和六元内酰胺的策略。通过在二氯甲烷或六氟-2-丙醇中使用易于获得的铱催化剂，以高至优异的产率和高选择性合成了多种内酰胺。
• Synthesis of 4-arylcoumarins via palladium-catalyzed arylation/cyclization of ortho-hydroxylcinnamates with diaryliodonium salts
  作者：Yang Yang、Jianwei Han、Xunshen Wu、Shujia Xu、Limin Wang

  DOI：10.1016/j.tetlet.2015.04.082

  日期：2015.6

  ortho-hydroxylcinnamate ester derivatives by using diaryliodonium(III) salts has been developed. With this method, 4-arylcoumarins were easily prepared in good to excellent yields under base-free conditions. Additionally, this protocol provided an efficient alternative for the preparation of related 4-arylated coumarin compounds which are useful in the access to 5-lipoxygenase inhibitors.

  已经开发了使用二芳基碘鎓（III）盐的钯催化的邻羟基肉桂酸酯衍生物的芳基化/环化反应。用这种方法，可以容易地在无碱条件下以良好的产率制备4-芳基香豆素。另外，该方案为制备相关的4-芳基香豆素化合物提供了有效的替代方法，该化合物可用于获得5-脂氧合酶抑制剂。
• NEGATIVE TYPE PHOTOSENSITIVE SILOXANE COMPOSITION AND METHODS FOR PRODUCING CURED FILM AND ELECTRONIC DEVICE USING THE SAME
  申请人：Merck Patent GmbH

  公开号：US20200333708A1

  公开（公告）日：2020-10-22

  [Object] To provide a negative type photosensitive siloxane composition capable of forming a cured film excellent in heat resistance and critical thickness for cracking [Means] The present invention provides a negative type photosensitive siloxane composition comprising : a polysiloxane containing silanol in a specific content, a particular photo base generator, and a solvent. The content of silanol is measured by FT-IR.

  【目标】提供一种负型光敏硅氧烷组合物，能形成热稳定性和临界厚度优异的固化膜。 【方法】本发明提供一种负型光敏硅氧烷组合物，包括：含有特定硅醇含量的聚硅氧烷、特定的光碱发生剂和溶剂。硅醇的含量由FT-IR测量。
• Prenylcoumarin with Rev-export inhibitory activity from Cnidii Monnieris Fructus
  作者：Satoru Tamura、Toshiaki Fujitani、Masafumi Kaneko、Nobutoshi Murakami

  DOI：10.1016/j.bmcl.2010.04.081

  日期：2010.6

  By use of the fission yeast expressing the model fusion protein comprised of GST, SV40 T antigen NLS, GFP, and Rev-NES in the bioassay, the prenylcoumarin osthol (1) was disclosed as the new Rev-export inhibitor from the MeOH extract of Cnidii Monnieris Fructus. Furthermore, 1 was also found to inhibit export the genuine Rev in HeLa cells by indirect fluorescent antibody technique. By the competitive experiment using the biotinylated probe 3, osthol (1) was revealed to inhibit nuclear export of Rev through a NES non-antagonistic mode. Structure-activity relationship analysis of several analogs of 1 clarified that both prenyl side chain and double bond adjacent to the lactone carbonyl residue play an important role in the Rev-export inhibitory potency of 1. (C) 2010 Elsevier Ltd. All rights reserved.
• Visible-Light-Driven, Photoredox-Catalyzed Cascade of <i>ortho-</i>Hydroxycinnamic Esters To Access 3-Fluoroalkylated Coumarins
  作者：Dan Song、Chao-Ming Wang、Zhi-Peng Ye、Peng-Ju Xia、Zhi-Xiong Deng、Jun-An Xiao、Hao-Yue Xiang、Hua Yang

  DOI：10.1021/acs.joc.9b00715

  日期：2019.6.7

  A general and straightforward protocol for di-/perfluoroalkylation of ortho-hydroxycinnamic esters via a photoredox-catalyzed cascade was developed to access a variety of 3-fluoroalkylated coumarins. This method was characterized by all-in-one synthetic design, simplified operation, mild reaction conditions, and broad substrate scope. Moreover, a sequential one-pot procedure starting from commercially available salicylaldehyde was also successfully realized to synthesize 3-fluoroalkylated coumarins.