methyl 4-methoxy-2-(phenylethynyl)benzoate | 1010733-54-6

• 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: methyl 4-methoxy-2-(phenylethynyl)benzoate
• 英文别名: Methyl 4-methoxy-2-(2-phenylethynyl)benzoate；methyl 4-methoxy-2-(2-phenylethynyl)benzoate
• CAS: 1010733-54-6
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: LBQXKWRZASMSKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-methoxy-2-(phenylethynyl)benzoate 在 三氟甲磺酸 、 哌啶 、 ammonium acetate 作用下， 以 乙腈 、 N,N-二甲基乙酰胺 为溶剂， 反应 0.5h， 以71%的产率得到6-methoxy-3-phenylisoquinolin-1(2H)-one
  参考文献：
  名称：

  三氟乙酸与乙酸铵介导的邻炔基芳基酯的顺序环化

  摘要：

  报道了三氟乙酸（TfOH）介导的邻炔基芳基酯和乙酸铵（NH 4 OAc）的顺序环化。该反应通过布朗斯台德酸介导的邻位分子内环化反应进行-炔基芳基酯接着乙酸铵参与取代反应，形成异喹啉-1-酮为主要产物。与大多数已知的异喹啉-1-酮合成方法不同，所报道的反应不需要金属催化剂。在少数情况下，获得了区域异构体–异吲哚啉-1-酮与异喹啉-1-酮。还分离了中间体化合物-异色酮-1-酮和异苯并呋喃-1-酮。相互转化实验表明，在布朗斯台德酸诱导的邻炔基芳基酯分子内环化过程中形成的区域异构体。采用这种新方法，可以以中等收率制备天然产物ruprechstyril。

  DOI：

  10.1016/j.tet.2020.131437
• 作为产物：
  描述：

  苯乙炔 、 methyl 4-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)benzoate 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以89%的产率得到methyl 4-methoxy-2-(phenylethynyl)benzoate
  参考文献：
  名称：

  Design, synthesis and analgesic properties of novel conformationally-restricted N-acylhydrazones (NAH)

  摘要：

  A set of six azaheterocycles were designed as conformationnaly-constrained N-acylhydrazones and tested as analgesics. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.075

文献信息

• Regioselective Synthesis of 4‐Aryl‐1,3‐dihydroxy‐2‐naphthoates through 1,2‐Aryl‐Migrative Ring Rearrangement Reaction and their Photoluminescence Properties
  作者：Hikaru Yanai、Teru Kawazoe、Nobuyuki Ishii、Bernhard Witulski、Takashi Matsumoto

  DOI：10.1002/chem.202101459

  日期：2021.8.5

  scaffold and that show photoluminescence emission from solid state as well as in solutions, were selectively synthesized from brominated lactol silyl ethers through the 1,2-aryl-migrative ring rearrangement reaction.

  4-Aryl-1,3-dihydroxy-2-naphthoates 具有不易接近的 1,2,3,4-四取代萘支架，并且在固态和溶液中都显示出光致发光发射，由溴化乳醇甲硅烷基醚选择性合成通过 1,2-芳基迁移环重排反应。
• Synthesis of 4-Chloroisocoumarins via Intramolecular Halolactonization of <i>o</i>-Alkynylbenzoates: PhICl₂-Mediated C–O/C–Cl Bond Formation
  作者：Linlin Xing、Yong Zhang、Bing Li、Yunfei Du

  DOI：10.1021/acs.orglett.9b00047

  日期：2019.4.5

  A series of 4-chloroisocoumarins were conveniently synthesized from o-alkynylbenzoates via PhICl2-mediated intramolecular cyclization under metal-free conditions. PhICl2 plays the role of both the oxidant and the chlorine source to enable oxidative C-O bond formation and introduction of the chlorine atom. The utility and practicability of this protocol have been exemplified by virtue of mild reaction conditions, high-yielding products, simplified purification, and gram-scale synthesis.
• Lactonization of 2-Alkynylbenzoates for the Assembly of Isochromenones Mediated by BF₃·Et₂O
  作者：Xiang Zhang、Xintong Wan、Ying Cong、Xiaohua Zhen、Qiao Li、Daisy Zhang-Negrerie、Yunfei Du、Kang Zhao

  DOI：10.1021/acs.joc.9b01601

  日期：2019.8.16

  A general and efficient lactonization method of readily available 2-alkynylbenzoates affording biologically important isochromenones has been realized via a solely BF3 center dot Et2O-mediated 6-endo-dig cyclization process under mild conditions. An alternative mechanistic pathway in which BF3 center dot Et2O activates the carbonyl of the ester moiety, rather than the alkyne triple bond, was postulated on the basis of control experiment results. Gram-scale reaction and further application for the assembly of more complex molecules demonstrated the practicability of the protocol.
• Triflic acid mediated sequential cyclization of ortho-alkynylarylesters with ammonium acetate
  作者：Maciej E. Domaradzki、Xiaochen Liu、Jiye Ong、Gyeongah Yu、Gan Zhang、Ariel Simantov、Eliyahu Perl、Yu Chen

  DOI：10.1016/j.tet.2020.131437

  日期：2020.9

  A triflic acid (TfOH) mediated sequential cyclization of ortho-alkynylarylesters and ammonium acetate (NH4OAc) was reported. The reaction took place via a Brønsted acid-mediated intramolecular cyclization of ortho-alkynylarylesters followed by an ammonium acetate participated substitution reaction, forming isoquinolin-1-ones as the major products. Different from most of the known synthetic methods

  报道了三氟乙酸（TfOH）介导的邻炔基芳基酯和乙酸铵（NH 4 OAc）的顺序环化。该反应通过布朗斯台德酸介导的邻位分子内环化反应进行-炔基芳基酯接着乙酸铵参与取代反应，形成异喹啉-1-酮为主要产物。与大多数已知的异喹啉-1-酮合成方法不同，所报道的反应不需要金属催化剂。在少数情况下，获得了区域异构体–异吲哚啉-1-酮与异喹啉-1-酮。还分离了中间体化合物-异色酮-1-酮和异苯并呋喃-1-酮。相互转化实验表明，在布朗斯台德酸诱导的邻炔基芳基酯分子内环化过程中形成的区域异构体。采用这种新方法，可以以中等收率制备天然产物ruprechstyril。
• Design, synthesis and analgesic properties of novel conformationally-restricted N-acylhydrazones (NAH)
  作者：Arthur E. Kümmerle、Marina M. Vieira、Martine Schmitt、Ana L.P. Miranda、Carlos A.M. Fraga、Jean-Jacques Bourguignon、Eliezer J. Barreiro

  DOI：10.1016/j.bmcl.2009.07.075

  日期：2009.9

  A set of six azaheterocycles were designed as conformationnaly-constrained N-acylhydrazones and tested as analgesics. (C) 2009 Elsevier Ltd. All rights reserved.