3-(tert-butyl)-1H-isochromen-1-one | 90991-96-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 3-(tert-butyl)-1H-isochromen-1-one
• 英文别名: 3-tert-butylisocoumarin；3-Tert-butylisochromen-1-one
• CAS: 90991-96-1
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: PNVFFMKMQWQYAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  300.5±35.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  邻羧基苯乙酸 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 三氯氧磷 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 3-(tert-butyl)-1H-isochromen-1-one
  参考文献：
  名称：

  Palladium catalyzed Suzuki Miyaura cross coupling of 3-chloroisochromen-1-one: synthesis of glomellin and reticulol analogues

  摘要：

  A facile protocol has been developed for a series of 3-substituted isochromen-1-ones utilizing Suzuki coupling strategy. The reaction of 3-chloroisochromen-1 one, 1 with different boronic acids utilizing PdCl2(PPh3)(2)-Ruphos catalytic system gave diversified 3-substituted isochromen-1-ones in excellent yields. The methodology has been utilized in the synthesis of glomellin and reticulol analogues. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.12.114

文献信息

• Palladium-catalyzed carbonylative synthesis of isocoumarins and phthalides by using phenyl formate as a carbon monoxide source
  作者：Qing Yuan、Zhen-Bang Chen、Fang-Ling Zhang、Yong-Ming Zhu

  DOI：10.1039/c6ob02409b

  日期：——

  A simple and efficient palladium-catalyzed intramolecular carbonylative synthesis of isocoumarins and phthalides from the easily available starting materials by employing phenyl formate as a CO surrogate has been achieved. The approach affords target compounds in good to excellent yields with the advantages of lower toxicity, milder conditions, easy operation and wide functional group tolerance.

  通过使用甲酸苯酯作为CO替代物，从容易获得的起始原料中，实现了一种简单有效的钯催化的香豆素和邻苯二酚的分子内羰基化合成反应。该方法以较低的毒性，较温和的条件，易于操作和宽泛的官能团耐受性等优点，以优异的收率提供了目标化合物。
• Palladium-Catalyzed Sequential Nucleophilic Addition/Oxidative Annulation of Bromoalkynes with Benzoic Acids To Construct Functionalized Isocoumarins
  作者：Guangbin Jiang、JianXiao Li、Chuanle Zhu、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.orglett.7b01919

  日期：2017.9.1

  for the preparation of 3-substituted isocoumarins via palladium-catalyzed nucleophilic addition/oxidative annulation of bromoalkynes with benzoic acids has been developed. Remarkably, preliminary mechanistic studies indicated that the transformation might proceed via a stereo- and regioselective nucleophilic addition and C–H functionalization procedure.

  已经开发了通过钯催化的溴炔烃与苯甲酸的亲核加成/氧化环化反应制备3-取代的香豆素的有效而有效的方案。值得注意的是，初步的机理研究表明，转化可能通过立体和区域选择性亲核加成和CH功能化程序进行。
• Sulfoxonium Ylides as Carbene Precursors: Rhodium(III)‐Catalyzed Sequential C−H Functionalization, Selective Enol Oxygen‐Atom Nucleophilic Addition, and Hydrolysis
  作者：Yuanqiong Huang、Xueli Lyu、Hongjian Song、Qingmin Wang

  DOI：10.1002/adsc.201900861

  日期：2019.11.19

  Herein, we report a protocol for Rh(III)‐catalyzed annulation reactions between oxazolines and sulfoxonium ylides via a sequence involving C−H activation, selective enol oxygen‐atom nucleophilic addition, and hydrolysis. This practical, operationally simple protocol has a wide substrate range, excellent regioselectivity, and moderate to good yields.

  在本文中，我们报告了通过Rh活化催化，选择性烯醇氧原子亲核加成和水解的序列，Rh（III）催化的恶唑啉和亚砜基鎓盐之间的环化反应的协议。该实用，操作简单的方案具有广泛的底物范围，出色的区域选择性以及中等至良好的产率。
• Synthesis of isocoumarins via thallation-olefination of benzoic acids
  作者：R. C. Larock、S. Varaprath、H. H. Lau、C. A. Fellows

  DOI：10.1021/ja00330a041

  日期：1984.9

  Par thallation de l'acide benzoique puis alcenylation en presence de PdCl 2 du carboxy-2 phenyl bis-trifluoroacetoxy thallium obtenu, on prepare diverses isocoumarines et dihydro-3,4 isocoumarines

  在 PdCl 2 du carboxy-2 苯基双-三氟乙酰氧基铊 obtenu 存在下进行部分 thallation de l'acide benzoique puis alcenylation，制备不同的异香豆素和二氢-3,4 异香豆素
• <i>p</i> -TSA-Based DESs as “Active Green Solvents” for Microwave Enhanced Cyclization of 2-Alkynyl-(hetero)-arylcarboxylates: an Alternative Access to 6-Substituted 3,4-Fused 2-Pyranones
  作者：Fabiola Curti、Matteo Tiecco、Valentina Pirovano、Raimondo Germani、Alessandro Caselli、Elisabetta Rossi、Giorgio Abbiati

  DOI：10.1002/ejoc.201801884

  日期：2019.3.7

  An acidic Deep Eutectic Solvent is an alternative environmental‐friendly “active” media for the microwave‐mediated synthesis of 6‐substituted 3,4‐fused 2‐pyranones.

  酸性深层共晶溶剂是微波介导的6取代3,4稠合2，吡喃酮的合成的替代环境友好型“活性”介质。