(Z)-3-(2-phenylethylidene)isobenzofuran-1(3H)-one | 1459243-96-9

• 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: (Z)-3-(2-phenylethylidene)isobenzofuran-1(3H)-one
• 英文别名: (3Z)-3-(2-phenylethylidene)-2-benzofuran-1-one
• CAS: 1459243-96-9
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: BEZYRANPMJKSGR-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-phenacylphthalide 在 sodium tetrahydroborate 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 0.33h， 生成 (Z)-3-(2-phenylethylidene)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  实用合成3-（2-芳基亚乙基）异吲哚啉-1-酮（类似AKS-182）和3-（2-芳基亚乙基）异苯并呋喃-1（3 H）-酮

  摘要：

  报道了一种简单实用的方法来合成3-（2-芳基-亚乙基）异吲哚啉-1-酮和3-（2-芳基-亚乙基）异苯并呋喃-1（3 H）-酮，产率高至优。 （E：Z）选择性。该方法涉及容易获得的3-（2-氧代-2-芳基乙基）异吲哚啉-1-酮和3-（2-氧代-2-芳基乙基）异苯并呋喃-1（3 H）-酮的顺序还原脱水反应。通过在乙腈中与K 2 CO 3进行碱催化的双键异构化来实现。使用该方法已经完成了对AKS-182的简明合成的开发。

  DOI：

  10.1016/j.tet.2019.130838

文献信息

• Regioselective One-Pot Synthesis of Isocoumarins and Phthalides from 2-Iodobenzoic Acids and Alkynes by Temperature Control
  作者：Manian Rajesh Kumar、Francis Mariaraj Irudayanathan、Joong Ho Moon、Sunwoo Lee

  DOI：10.1002/adsc.201300561

  日期：2013.11.11

  AbstractCopper‐catalyzed coupling reaction of 2‐iodobenzoic acids and alkynes such as terminal acetylenes, alkynyl carboxylic acids, and trimethylsilylacetylene selectively afforded isocoumarins and phthalides in the presence of cesium carbonate (Cs2CO3) and dimethyl sulfoxide (DMSO). Among the regioselective products, only the 6‐endo‐dig product, isocoumarin, was formed at 100 °C, and the 5‐exo‐dig product, phthalide, was formed as a major product at 25 °C. A variety of alkynes produced the corresponding isocoumarins and phthalides in good yields. A mechanism is suggested in which the formation of 2‐alkynylbenzoic acid as an intermediate via Sonogashira‐type coupling was ruled out in the reaction pathway.magnified image
• 3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators
  作者：Giorgio Ortar、Aniello Schiano Moriello、Enrico Morera、Marianna Nalli、Vincenzo Di Marzo、Luciano De Petrocellis

  DOI：10.1016/j.bmcl.2013.08.039

  日期：2013.10

  Following the recent identification of the naturally occurring 3-ylidene-4,5-dihydrophthalide ligustilide and its oxidation product dehydroligustilide as novel TRPA1 modulators, a series of seventeen 3-ylide-nephthalides was synthesized and tested on TRPA1 and TRPM8 channels. Most of these compounds acted as strong modulators of the two channel types with EC50 and/or IC50 values distinctly lower than those of the reference compounds. (C) 2013 Elsevier Ltd. All rights reserved.
• Practical synthesis of 3-(2-arylethylidene)isoindolin-1-ones (analogues of AKS-182) and 3-(2-arylethylidene)isobenzofuran-1(3H)-ones
  作者：Mario Ordóñez、Angel Palillero-Cisneros、Victoria Labastida-Galván、Joel Luis Terán-Vázquez

  DOI：10.1016/j.tet.2019.130838

  日期：2020.1

  method is reported for the synthesis of 3-(2-aryl-ethylidene)isoindolin-1-ones and 3-(2-arylethylidene)isobenzofuran-1(3H)-ones, proceeding with good to excellent yields and (E:Z) selectivity. This methodology involves the sequential reduction-dehydration reaction of readily obtained 3-(2-oxo-2-arylethyl)isoindolin-1-ones and 3-(2-oxo-2-arylethyl)isobenzofuran-1(3H)-ones followed by a base-catalyzed

  报道了一种简单实用的方法来合成3-（2-芳基-亚乙基）异吲哚啉-1-酮和3-（2-芳基-亚乙基）异苯并呋喃-1（3 H）-酮，产率高至优。 （E：Z）选择性。该方法涉及容易获得的3-（2-氧代-2-芳基乙基）异吲哚啉-1-酮和3-（2-氧代-2-芳基乙基）异苯并呋喃-1（3 H）-酮的顺序还原脱水反应。通过在乙腈中与K 2 CO 3进行碱催化的双键异构化来实现。使用该方法已经完成了对AKS-182的简明合成的开发。