(Z)-3-(4-(dimethylamino)benzylidene)isobenzofuran-1(3H)-one | 145864-00-2

• 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-(4-(dimethylamino)benzylidene)isobenzofuran-1(3H)-one
• 英文别名: z-3-(4-Dimethylaminobenzylidene)phthalide；(3Z)-3-[[4-(dimethylamino)phenyl]methylidene]-2-benzofuran-1-one
• CAS: 145864-00-2
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: QPZTYZIPIJZQOV-WJDWOHSUSA-N

物化性质

• 沸点：
  440.2±45.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴苯酞 在 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.0h， 生成 (Z)-3-(4-(dimethylamino)benzylidene)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  Shevchuk, M. I.; Shpak, S. T.; Tolochko, A. F., Journal of general chemistry of the USSR, 1987, vol. 57, p. 705 - 709

  摘要：

  DOI：

文献信息

• [EN] AURONES AND METHODS OF USING AURONES TO TREAT TUBERCULOSIS<br/>[FR] AURONES ET MÉTHODES D'UTILISATION D'AURONES POUR TRAITER LA TUBERCULOSE
  申请人：MIDDLE TENNESSEE STATE UNIV

  公开号：WO2020223439A1

  公开（公告）日：2020-11-05

  This disclosure describes compounds, compositions, and methods for treating or preventing infection or disease including, in some specific embodiments, treating or preventing tuberculosis and/or infection with Mycobacterium tuberculosis (Mtb). In one aspect, this disclosure describes aurones including, for example, aurone 9504, aurone 9505, aurone 9501, aurone 9510, aurone AA2A, and aurone AA8, compositions including aurones, and methods of using aurones for treating or preventing tuberculosis.

  这份披露描述了治疗或预防感染或疾病的化合物、组合物和方法，包括在某些具体实施例中，治疗或预防结核病和/或结核分枝杆菌（Mtb）感染。在一个方面，这份披露描述了包括aurone 9504、aurone 9505、aurone 9501、aurone 9510、aurone AA2A和aurone AA8在内的aurones，包括aurones的组合物，以及使用aurones治疗或预防结核病的方法。
• 1-Phenyl-1,2-benziodoxol-3-(1<i>H</i> )-one as Synthon for Phthalide Synthesis through Pd-Free, Base-Free, Sonogashira-Type Coupling Cyclization Reaction
  作者：Ahmad A. Almasalma、Esteban Mejía

  DOI：10.1002/ejoc.201700940

  日期：2018.1.17

  heterocycles have found broad application as atom-transfer reagents for organic synthesis. Among them, 1-Phenyl-1,2-benziodoxol-3-(1H)-one is known as a traditional benzyne precursor, but no further synthetic applications have been reported. Herein, we report the first synthetic application of 1-phenylbenzidoxole to the synthesis of Phthalides using only CuI as catalyst. High selectivity and yield were achieved

  高价碘 (III) 五元杂环已被广泛用作有机合成的原子转移试剂。其中，1-Phenyl-1,2-benziodoxol-3-(1H)-one 被称为传统的苄前体，但没有进一步的合成应用报道。在此，我们报告了仅使用 CuI 作为催化剂的 1-苯基苯并氧杂环戊烷在邻苯二甲酸酯合成中的首次合成应用。在温和的反应条件下实现了高选择性和高产率，并具有良好的官能团耐受性。在我们的研究过程中，研究了不同反应条件下不同 CuI 和 CuII 催化剂的效率。离去基团的性质、底物上的取代基和温度对产率和选择性都起着重要作用。而且，
• The chemistry of phthalide-3-carboxylic acid - I decarboxylation in the presence of aldehydes
  作者：Rolf H. Prager、Carl H. Schiesser

  DOI：10.1016/s0040-4020(01)91799-5

  日期：1984.1

  The decarboxylation of phthalide-3-carboxylic acid (3-oxo-l,3-dihydroisobenzofuran-1-carboxylic acid) has been studied in the melt, in dimethylsulfoxide, and in the presence of aromatic aldehydes. The latter are efficiently trapped to produce mixtures of 3-arylidene-phthalides and 3-(arylhydroxymethyl)phthalides. Kinetic and other evidence supports the proposal that this reaction occurs in a tight

  已经在熔体中，在二甲基亚砜中和在芳族醛存在下研究了邻苯二甲酸酯-3-羧酸（3-氧代-1，3-二氢异苯并呋喃-1-羧酸）的脱羧。后者被有效地捕集以产生3-亚芳基-邻苯二甲酸酯和3-（芳基羟甲基）邻苯二甲酸酯的混合物。动力学和其他证据支持这一反应以紧密的循环过渡态发生的提议。
• 1,5,7‐Triazabicyclo[4.4.0]dec‐5‐ene (TBD): An Organocatalyst for Rapid Access to 3‐Hydroxyisoindolin‐1‐ones
  作者：Chunling Blue Lan、Karine Auclair

  DOI：10.1002/ejoc.202400071

  日期：2024.3.25

  The readily available organocatalyst 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD) was used for the rapid synthesis of 3‐hydroxyisoindolin‐1‐ones from 3‐alkylidenephthalides. The transformation occurs at room temperature and requires less solvent than traditional methods, providing a more sustainable synthetic option to access 3‐hydroxyisoindolin‐1‐ones with broad scope. Elaboration of the products to diverse scaffolds as well as synthesis of biologically active compounds are demonstrated.

  摘要 利用容易获得的有机催化剂 1,5,7-三氮杂双环[4.4.0]癸-5-烯（TBD），从 3-亚烷基酞化物快速合成 3-羟基异吲哚啉-1-酮。与传统方法相比，该转化过程在室温下进行，所需的溶剂更少，为获得范围广泛的 3-羟基异吲哚啉-1-酮提供了更可持续的合成选择。该研究展示了如何将产品加工成不同的支架以及合成具有生物活性的化合物。
• 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