ethyl 1,3-dihydroisobenzofuran-5-carboxylate | 1255217-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: ethyl 1,3-dihydroisobenzofuran-5-carboxylate
• 英文别名: Ethyl 1,3-dihydro-2-benzofuran-5-carboxylate
• CAS: 1255217-89-0
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: DEXXBZZYNMYAOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  ethyl 1,3-dihydroisobenzofuran-5-carboxylate 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 以53%的产率得到1,3-二氢-1-氧代异苯并呋喃-5-羧酸乙酯
  参考文献：
  名称：

  Synthesis of phthalides from bis-propargyl ethers: use of Garratt–Braverman cyclization to construct the phthalans and IBX as a new reagent for subsequent oxidation

  摘要：

  An efficient route to phthalides is described starting from easily available bis-propargyl ethers. The method involves Garratt-Braverman cyclization of the ethers to phthalans which are then efficiently oxidized to the phthalides by iodoxy benzoic acid (IBX) which has been shown to be a superior reagent in terms of yield and reagent stoichiometry for such a transformation in comparison with more commonly used KMnO4/CuSO4 reagent. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.09.036
• 作为产物：
  描述：

  在 silver hexafluoroantimonate 、 di-μ-chlorobis(norbornadiene)dirhodium(I) 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到ethyl 1,3-dihydroisobenzofuran-5-carboxylate
  参考文献：
  名称：

  使用新戊烯系的偶联伙伴进行反应发现：电子缺乏的二烯炔的环异构化/氧化

  摘要：

  描述了铑催化的环二烯异构化和拴系二烯的氧化，用于合成茚满。辅助的裂解/烯烃化方法（也在本文中进行了描述）提供了对拴系的炔-二烯二酸酯底物的新颖访问。报道的方法规避了当前的局限性，并扩大了反需求Diels-Alder型环加成反应的范围。在当前方法中，涉及基于丙二酸酯，醚和磺酰胺基系链的传统发现底物是有问题的，强调了新戊二烯系链的底物在反应发现中的独特优势。

  DOI：

  10.1021/acs.orglett.7b02261

文献信息

• Ruthenium Carbene Mediated [2+2+2] Cyclotrimerizations
  作者：Javier Pérez-Castells、Álvaro Mallagaray、Sandra Medina、Gema Domínguez

  DOI：10.1055/s-0030-1258521

  日期：2010.9

  Second-generation Grubbs’ catalyst and Hoveyda-Grubbs’ catalyst are able to catalyze both crossed [2+2+2] cyclotrimerization of diynes with alkynes and di- or trimerizations of diynes. Selection of the reaction conditions allows us to favor one particular process. The process is selective when applied to unsymmetric diynes.

  第二代格拉布斯催化剂和霍韦达-格拉布斯催化剂既能催化二炔与炔烃的交叉[2+2+2]环三聚反应，也能催化二炔的二聚或三聚反应。通过选择反应条件，我们可以选择一种特定的工艺。该过程对不对称二炔具有选择性。
• Reactivity of Electron-Deficient Alkynes on Gold Nanoparticles
  作者：Antonio Leyva-Pérez、Judit Oliver-Meseguer、Jose R. Cabrero-Antonino、Paula Rubio-Marqués、Pedro Serna、Saud I. Al-Resayes、Avelino Corma

  DOI：10.1021/cs400362c

  日期：2013.8.2

  Propiolates cyclotrimerize in the presence of catalytic amounts of gold nanoparticles to give aryl benzoates in high yields and with turnover frequencies of thousands per hour. Types of alkynes other than propiolates do not react, and, if molecular oxygen is present and dissociated by the gold nanoparticles, electron-rich arenes engage with the propiolate to form a new C-C bond. The activation of propiolates and electron-rich arenes to form C-C bonds, beyond gold-catalyzed Michael additions, constitutes a new example of how and where gold nanoparticles modify the electronic density of unsaturated C-C bonds and opens the door to future transformations.
• Reaction Discovery Using Neopentylene-Tethered Coupling Partners: Cycloisomerization/Oxidation of Electron-Deficient Dienynes
  作者：Nicholas J. Kramer、Tung T. Hoang、Gregory B. Dudley

  DOI：10.1021/acs.orglett.7b02261

  日期：2017.9.1

  A rhodium-catalyzed cycloisomerization and oxidation of tethered dienynes for the synthesis of indanes is described. An auxiliary fragmentation/olefination method (also described herein) provides novel access to tethered alkyne-dienoate substrates. The reported method circumvents current limitations in and expands the scope of inverse-demand Diels–Alder-type cycloadditions. Traditional discovery substrates

  描述了铑催化的环二烯异构化和拴系二烯的氧化，用于合成茚满。辅助的裂解/烯烃化方法（也在本文中进行了描述）提供了对拴系的炔-二烯二酸酯底物的新颖访问。报道的方法规避了当前的局限性，并扩大了反需求Diels-Alder型环加成反应的范围。在当前方法中，涉及基于丙二酸酯，醚和磺酰胺基系链的传统发现底物是有问题的，强调了新戊二烯系链的底物在反应发现中的独特优势。
• Synthesis of phthalides from bis-propargyl ethers: use of Garratt–Braverman cyclization to construct the phthalans and IBX as a new reagent for subsequent oxidation
  作者：Arpita Panja、Eshani Das、Manasi Maji、Amit Basak

  DOI：10.1016/j.tetlet.2015.09.036

  日期：2015.10

  An efficient route to phthalides is described starting from easily available bis-propargyl ethers. The method involves Garratt-Braverman cyclization of the ethers to phthalans which are then efficiently oxidized to the phthalides by iodoxy benzoic acid (IBX) which has been shown to be a superior reagent in terms of yield and reagent stoichiometry for such a transformation in comparison with more commonly used KMnO4/CuSO4 reagent. (C) 2015 Elsevier Ltd. All rights reserved.