3-ethyl-3-hydroxybenzoisofuran-1-one | 40893-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-ethyl-3-hydroxybenzoisofuran-1-one
• 英文别名: 3-ethyl-3-hydroxyisobenzofuran-1(3H)-one；3-Ethyl-3-hydroxy-2-benzofuran-1(3H)-one；3-ethyl-3-hydroxy-2-benzofuran-1-one
• CAS: 40893-22-9
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: OZOJNUXHWHJKQG-UHFFFAOYSA-N

物化性质

• 沸点：
  376.0±42.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-ethyl-3-hydroxybenzoisofuran-1-one 在 sodium tetrahydroborate 作用下， 生成 丁苯酞杂质
  参考文献：
  名称：

  Synthesis, resolution, and antiplatelet activity of 3-substituted 1(3H)-isobenzofuranone

  摘要：

  A series of 3-substituted-1(3H)-isobenzofuranone 6a-g and 7a-g were synthesized from phthalic anhydride. The compound 6a-g was resolved. The antiplatelet activities of these compounds were evaluated using in vitro experiment of platelet aggregation. The levels of antiplatelet activity were displayed as following sequence: l-isomer > dl-isomer > d-isomer, respectively. The alkylphthalide is more active than the corresponding alkenephthalide. All these compounds were less active than n-butylphthalide (NBP, 6c) and Aspirin (Asp). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.082
• 作为产物：
  描述：

  2-丙酰苯甲酸 以 乙醇 为溶剂， 生成 3-ethyl-3-hydroxybenzoisofuran-1-one
  参考文献：
  名称：

  Ring-Chain Tautomerism. Part 10. The Reaction of Oxocarboxylic Acids with Diazodiphenylmethane

  摘要：

  一系列羧酸酯化与二苯甲烷重氮化合物的速率系数已在30.0°C的乙醇或2-甲氧基乙醇中确定。这些速率以及与模型化合物的反应速率已用于估算羧酸酯的环-链互变异构的平衡常数。

  DOI：

  10.1135/cccc19991601

文献信息

• Carbene‐Catalyzed Dynamic Kinetic Resolution and Asymmetric Acylation of Hydroxyphthalides and Related Natural Products
  作者：Yingguo Liu、Pankaj Kumar Majhi、Runjiang Song、Chengli Mou、Lin Hao、Huifang Chai、Zhichao Jin、Yonggui Robin Chi

  DOI：10.1002/anie.201912926

  日期：2020.3.2

  A catalytic dynamic kinetic resolution and asymmetric acylation reaction of hydroxyphthalides is developed. The reaction involves formation of a carbene catalyst derived chiral acyl azolium intermediate that effectively differentiates the two enantiomers of racemic hydroxyphthalides. The method allows quick access to enantiomerically enriched phthalidyl esters with proven applications in medicine.

  研究了羟基邻苯二酚的催化动力学动力学拆分和不对称酰化反应。该反应涉及形成卡宾催化剂衍生的手性酰基偶氮中间体，该中间体可有效区分外消旋羟基邻苯二酚的两种对映异构体。该方法可以快速获得对映体富集的邻苯二甲酸酯，并已在医学中得到证实的应用。它还可以对天然产物和其他含有缩醛/缩酮基团的功能分子（例如花冠素和纤维状内酯C）进行不对称修饰。
• On the reactions of 1,3-isoquinolinediones with singlet oxygen
  作者：Ke-Qing Ling、Jia-Hai Ye、Xian-Yang Chen、De-Jian Ma、Jian-Hua Xu

  DOI：10.1016/s0040-4020(99)00502-5

  日期：1999.7

  view of these observations, an unusual [4+2] cycloaddition of the electron-rich enol 21 with singlet oxygen is proposed to be responsible for the formation of products 7 and 16, while products 6, 14 and 15 arise from both the [4+2] cycloaddition and the usual Schenck ene reaction pathways. This special diene reactivity of the isoquinolinone system towards singlet oxygen is further interpreted by frontier

  1，3-异喹啉二酮5和4-烷基化的1，3-异喹啉二酮13与单线态氧的反应完全被烯醇化控制，并且在吡啶作为碱和氢键受体的存在下在苯中平稳地进行。该产品是三酮类6和benzoisofuranones 7为5，和氢过氧化物14，氢氧化物15和benzoisofuranones 16为13。发现6的水解提供了异吲哚酮8而不是产物7，而氢过氧化物14a的碱性裂解不仅产生16a，还产生异吲哚酮19a。鉴于这些观察结果，提出了富电子的烯醇21与单线态氧的不寻常的[4 + 2]环加成反应，导致产物7和16的形成，而产物6、14和15则由[ [4 + 2]环加成反应和通常的Schenck烯反应途径。前沿分子轨道（FMO）相互作用的考虑进一步解释了异喹啉酮系统对单线态氧的这种特殊的二烯反应性。
• Dye-sensitized photooxygenations of 1,3-isoquinolinediones
  作者：Ling Ke-Qing、Ji Gang、Cai Hu、Xu Jian-Hua

  DOI：10.1016/s0040-4039(98)00344-x

  日期：1998.4

  (RB) in methanol or by tetraphenylporphin (TPP) in the presence of pyridine as a base and a cosolvent in benzene. The products are the corresponding 1,3,4-isoquinolinetriones 2a-2e and methyl 1-hydroxy-3-oxoisoindole-1-carboxylates 3b-3e in methanol and the triketones 2a-2e and the 3-hydroxy-3-alkyl (aryl)aminocarbonylbenzoisofuran-1-ones 4b-4e in benzene-pyridine. TPP sensitized photooxygenations of the

  1,3-异喹啉二酮1a-1e的单线态氧反应可通过阴离子敏化剂Rose Bengal（RB）在甲醇中或四苯基卟啉（TPP）在吡啶作为碱和在苯中的助溶剂存在下进行敏化。产物是在甲醇中的相应1,3,4-异喹啉三酮2a-2e和1-羟基-3-氧代异吲哚-1-羧酸甲酯3b-3e以及三酮2a-2e和3-羟基-3-烷基（芳基）在苯吡啶中的氨基羰基苯并异呋喃-1-酮4b-4e。TPP对4-烷基化的1,3-异喹啉二酮5a-5c进行光氧化可得到4-烷基-4-羟基-1,3-异喹啉二酮6a-6c，4-烷基-4-氢过氧-1,3-异喹啉二酮7a-7c和3-烷基-3-羟基苯并异呋喃-1-酮8a-8b。已经提出了反应机理。
• Process for preparing diphenyl ethers
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0306096A1

  公开（公告）日：1989-03-08

  Diphenyl ether derivatives of formula II wherein R₁ represents a hydrogen or halogen atom or an alkyl or haloalkyl group, R₂ and R₃, which may be the same or different, each independently represents a hydrogen or halogen atom, or an alkyl, haloalkyl, nitro or cyano group, R₄ represents an alkyl group and X represents an oxygen or sulphur atom, useful as intermediates in the preparation of diphenyl ether herbicides, are prepared by treating a compound of formula III , where R₁, R₂, R₃ and X are as defined above and R₆ is a hydrogen atom or an alkyl group, with an alkali under hydrolysing conditions.

  式 II 的二苯醚衍生物 式中 R₁ 代表氢原子或卤素原子或烷基或卤代烷基，R₂ 和 R₃ 可以相同或不同，各自独立地代表氢原子或卤素原子或烷基、卤代烷基、硝基或氰基，R₄ 代表烷基，X 代表氧原子或硫原子。 其中 R₁、R₂、R₃ 和 X 如上文所定义，R₆ 是氢原子或烷基。
• US4927945A
  申请人：——

  公开号：US4927945A

  公开（公告）日：1990-05-22