3-(4-甲氧基苯基)丙酸甲酯 | 7515-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(4-甲氧基苯基)丙酸甲酯
• 英文名称: methyl 3-(4-methoxyphenyl)propynoate
• 英文别名: methyl 3-(4-methoxyphenyl)propiolate；methyl 4-methoxyphenylpropiolate；methyl (p-methoxy)phenylpropiolate；methyl 3-(4-methoxyphenyl)-2-propynoate；methyl 3-(4-methoxyphenyl)prop-2-ynoate
• CAS: 7515-17-5
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: MIWQTCPRUGGBLM-UHFFFAOYSA-N

物化性质

• 熔点：
  45-46 °C
• 沸点：
  290.7±23.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2918990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温且干燥

反应信息

• 作为反应物：
  描述：

  3-(4-甲氧基苯基)丙酸甲酯 在 吡啶 、 氢气 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 4-甲氧基肉桂酸
  参考文献：
  名称：

  脂肪族烯基酰胺的对映选择性钯催化的氧化级联环化

  摘要：

  据报道，Pd（TFA）2 /（S，S）-diPh-pyrox的催化剂体系可在温和的好氧条件下促进链烯键合的脂肪族丙烯酰胺的高效对映选择性氧化级联环化反应。已经以高收率和优异的对映选择性合成了一系列吡咯并咪唑衍生物。氘标记实验表明，该反应以高选择性通过反氨基palpalation（anti -AP）途径进行。已计算出抗-AP步骤的过渡态，以说明观察到的对映选择性。

  DOI：

  10.1021/acs.orglett.6b03410
• 作为产物：
  描述：

  对甲氧基苯甲酰氯 以 甲苯 为溶剂， 250.0 ℃ 、133.32 Pa 条件下， 生成 3-(4-甲氧基苯基)丙酸甲酯
  参考文献：
  名称：

  Pyranone, Thiopyranone, and Pyridone Inhibitors of Phosphatidylinositol 3-Kinase Related Kinases. Structure−Activity Relationships for DNA-Dependent Protein Kinase Inhibition, and Identification of the First Potent and Selective Inhibitor of the Ataxia Telangiectasia Mutated Kinase

  摘要：

  Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholino-pyran-4-ones and 2-morpholino-thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6-(morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.

  DOI：

  10.1021/jm061121y

文献信息

• Construction of 2-Substituted-3-Functionalized Benzofurans via Intramolecular Heck Coupling: Application to Enantioselective Total Synthesis of Daphnodorin B
  作者：Hu Yuan、Kai-Jian Bi、Bo Li、Rong-Cai Yue、Ji Ye、Yun-Heng Shen、Lei Shan、Hui-Zi Jin、Qing-Yan Sun、Wei-Dong Zhang

  DOI：10.1021/ol4021095

  日期：2013.9.20

  A novel approach was developed for the synthesis of 2-substituted-3-functionalized benzofurans, using an intramolecular Heck reaction which was further applied in the first enantioselective total synthesis of Daphnodorin B.

  利用分子内的Heck反应，开发了一种用于合成2-取代的3-官能化的苯并呋喃的新方法，该方法还被用于Daphnodorin B的首次对映选择性全合成。
• Palladium-Catalyzed Hydroalkylation of Alkynes with Cyclopropanols: Access to γ,δ-Unsaturated Ketones
  作者：Hao Liu、Zhiyuan Fu、Shang Gao、Yue Huang、Aijun Lin、Hequan Yao

  DOI：10.1002/adsc.201800200

  日期：2018.8.17

  A palladium‐catalyzed hydroalkylation of alkynes with cyclopropanols has been developed. This reaction provided a straightforward way to the synthesis of γ,δ‐unsaturated ketones in moderate to good yields, exhibiting high atom economy and Z/E selectivity. Deuterated tri‐substituted alkenes could also be expediently produced by using deuterium oxide as a co‐solvent.

  已经开发了钯与环丙醇的炔烃加氢烷基化反应。该反应为中等到良好的产率合成γ，δ-不饱和酮提供了直接的方法，具有很高的原子经济性和Z / E选择性。氘化的三取代烯烃也可以方便地使用氧化氘作为助溶剂来生产。
• Synthesis of 1-Amino-2<i>H</i>-quinolizin-2-one Scaffolds by Tandem Silver Catalysis
  作者：Xiao-Long Min、Chao Sun、Ying He

  DOI：10.1021/acs.orglett.8b03935

  日期：2019.2.1

  An efficient tandem cycloisomerization–amination reaction catalyzed by silver is described. This rapid and atom-economic reaction delivered 1-amino-2H-quinolizin-2-one scaffolds in high yields under mild conditions. The reaction could be extended to an asymmetric version albeit with moderate enantioselective excess of the products. In addition, the products can be easily reduced into various azabicycles

  描述了一种由银催化的有效的串联环异构化-胺化反应。这种迅速而经济的反应在温和的条件下以高收率递送了1-氨基-2 H-喹诺嗪-2-酮骨架。该反应可扩展至不对称形式，尽管具有中等对映选择性过量的产物。另外，可以容易地将产物还原为含有4-吡啶酮的各种氮杂双环，这是有机合成中的重要组成部分。
• Copper-Catalyzed Domino Synthesis of Benzo[4,5]imidazo[1,2-<i>a</i>]pyrimidin-4(10<i>H</i>)-ones using Cyanamide as a Building Block
  作者：Zhenbang Lou、Xudong Wu、Haijun Yang、Changjin Zhu、Hua Fu

  DOI：10.1002/adsc.201500577

  日期：2015.12.14

  An efficient and practical copper-catalyzed domino synthesis of benzo[4,5]imidazo[1,2-a]pyrimidin-4(10H)-ones has been developed. The protocol uses N-(2-halophenyl)-3-alkylpropiolamides and cyanamide as the starting materials, inexpensive copper(I) iodide and pipecolinic acid as the catalyst and ligand, and the corresponding products were obtained in moderate to good yields.

  开发了一种高效实用的苯并[4,5]咪唑并[1,2 - a ]嘧啶-4（10 H）-酮的铜催化多米诺合成。该方案以N-（2-卤代苯基）-3-烷基丙酰胺和氰酰胺为起始原料，廉价的碘化铜（I）和哌啉酸为催化剂和配体，并以中等至良好的产率获得了相应的产物。
• Palladium-catalyzed cascade carboesterification of norbornene with alkynes
  作者：Wanqing Wu、Can Li、Jianxiao Li、Huanfeng Jiang

  DOI：10.1039/c8ob01799a

  日期：——

  An efficient and convenient palladium-catalyzed cascade carboesterification of norbornenes (NBE) with alkynes has been accomplished to afford functionalized α-methylene γ-lactone and tetrahydrofuran derivatives in good to excellent yields. This new strategy exhibits excellent atom- and step-economy, good functional group tolerance and broad substrate scope. In particular, NBE-palladium species was

  已经完成了高效且方便的降冰片烯（NBE）与炔烃的钯催化的级联碳酯化反应，从而以良好或优异的收率提供了官能化的α-亚甲基γ-内酯和四氢呋喃衍生物。这种新策略具有出色的原子和步阶经济性，良好的官能团耐受性和广泛的底物范围。特别地，提出了NBE-钯物质是催化循环中抑制β-H消除过程的关键中间体。值得注意的是，开发的协议为构建各种含氧杂环骨架提供了直接而实用的工具，说明了在合成化学和药物化学中的有希望的应用。