(Z)-3-(2-fluorobenzylidene)isobenzofuran-1(3H)-one | 42086-74-8

• 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-fluorobenzylidene)isobenzofuran-1(3H)-one
• 英文别名: (3Z)-3-[(2-fluorophenyl)methylidene]-2-benzofuran-1-one
• CAS: 42086-74-8
• 化学式: C₁₅H₉FO₂
• 分子量: 240.234
• InChiKey: PUBGXBUCMSVVCN-ZROIWOOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-(2-fluorobenzylidene)isobenzofuran-1(3H)-one 在 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-[2-(2-Fluoro-phenyl)-acetyl]-benzoic acid anion
  参考文献：
  名称：

  Base-catalysed hydrolysis of ?-lactones: reactivity-structure correlations for 3-(aryl- and alkylmethylene)-(Z)-1(3H)-isobenzofuranones

  摘要：

  DOI：

  10.1002/(sici)1099-1395(199711)10:11<841::aid-pca950>3.0.co;2-6
• 作为产物：
  描述：

  2-碘苯甲酸 、 1-乙炔基-2-氟苯 在 copper(l) iodide 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以62%的产率得到(Z)-3-(2-fluorobenzylidene)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  通过温度控制从2-碘苯甲酸和炔烃区域选择性一锅法合成异香豆素和邻苯二甲酸酯

  摘要：

  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

  DOI：

  10.1002/adsc.201300561

文献信息

• Ir‐SpinPHOX Catalyzed Enantioselective Hydrogenation of 3‐Ylidenephthalides
  作者：Yao Ge、Zhaobin Han、Zheng Wang、Chen‐Guo Feng、Qian Zhao、Guo‐Qiang Lin、Kuiling Ding

  DOI：10.1002/anie.201807639

  日期：2018.10

  The first asymmetric hydrogenation of 3‐ylidenephthalides has been developed using the IrI complex of a spiro[4,4]‐1,6‐nonadiene‐based phosphine‐oxazoline ligand (SpinPHOX) as the catalyst, affording a wide variety of chiral 3‐substituted phthalides in excellent enantiomeric excesses (up to 98 % ee). The utility of the protocol has been demonstrated in the asymmetric synthesis of chiral drugs NBP and

  使用基于螺[4,4] -1,6-壬二烯的膦-恶唑啉配体（SpinPHOX）的Ir I络合物作为催化剂开发了3种亚萘二甲酸酯的第一个不对称氢化反应，提供了多种手性3出色的对映体过量（最高ee达98％）的预取代邻苯二甲酸酯。该协议的实用性已在手性药物NBP和BZP前体以及天然产物创心酚和邻苯二甲酰亚胺的不对称合成中得到证明。
• Krasnec, Ludovit; Hrnciar, Pavol; Gaplovsky, Anton, Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 4, p. 1072 - 1078
  作者：Krasnec, Ludovit、Hrnciar, Pavol、Gaplovsky, Anton

  DOI：——

  日期：——
• 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
• Base-catalysed hydrolysis of ?-lactones: reactivity-structure correlations for 3-(aryl- and alkylmethylene)-(Z)-1(3H)-isobenzofuranones
  作者：Keith Bowden、Kanwaljit Agnihotri、Richard J. Ranson、Alexander Perj�ssy、Pavol Hrn?iar、Ivan Proke?、Walter M. Fabian

  DOI：10.1002/(sici)1099-1395(199711)10:11<841::aid-pca950>3.0.co;2-6

  日期：1997.11