6-chloro-3-methyl-1H-isochromene-1-one | 61436-71-3

• 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: 6-chloro-3-methyl-1H-isochromene-1-one
• 英文别名: 6-chloro-3-methyl-1H-isochromen-1-one；6-chloro-3-methylisochromen-1-one；6-chloro-3-methyl-isochromen-1-one；3-Methyl-6-chlor-isocumarin；6-Chloro-3-methyl-1H-2-benzopyran-1-one
• CAS: 61436-71-3
• 化学式: C₁₀H₇ClO₂
• 分子量: 194.617
• InChiKey: ICDGLSSMLXKXIL-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C
• 沸点：
  323.0±42.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  6-chloro-3-methyl-3,4-dihydroisocoumarin 以75%的产率得到
  参考文献：
  名称：

  BHIDE B. H.; GUPTA V. P., INDIAN J. CHEM., 1979, B 17, NO 3, 295

  摘要：

  DOI：

文献信息

• Rh(III)-Catalyzed Oxidative Coupling of Benzoic Acids with Geminal-Substituted Vinyl Acetates: Synthesis of 3-Substituted Isocoumarins
  作者：Mingliang Zhang、Hui-Jun Zhang、Tiantian Han、Wenqing Ruan、Ting-Bin Wen

  DOI：10.1021/jo502231y

  日期：2015.1.2

  The Rh(III)-catalyzed C–H activation initiated cyclization of benzoic acids with electron-rich geminal-substituted vinyl acetates was described. The reaction was employed to prepare a range of 3-aryl and 3-alkyl substituted isocoumarins selectively.

  描述了Rh（III）催化的C–H活化引发了富含电子的双键取代的乙酸乙烯酯对苯甲酸的环化反应。该反应用于选择性地制备一定范围的3-芳基和3-烷基取代的异香豆素。
• Copper nanoparticles catalyzed economical synthesis of 3-substituted isocoumarins from 2-chlorobenzoic acids/amides and 1,3-diketones
  作者：Xiaowen Wang、Chaolong Wu、Youwen Sun、Xiaoquan Yao

  DOI：10.1016/j.tetlet.2017.07.001

  日期：2017.8

  Copper nanoparticles were utilized as a highly efficient catalyst for a facile and economical synthesis of 3-substituted isocoumarins with 2-chlorobenzoic acids and 1,3-diketones as starting materials. The copper nanoparticles catalyst showed highly catalytic activity for the 2-chloro-substituted substrates to afford 3-substituted isocoumarins in good to excellent yields. Furthermore, good catalytic

  铜纳米颗粒被用作一种高效催化剂，用于以2-氯苯甲酸和1,3-二酮为起始原料轻松，经济地合成3-取代的香豆素。铜纳米颗粒催化剂对2-氯取代的底物表现出高催化活性，以良好至优异的产率提供3-取代的异香豆素。此外，当使用2-氯苯甲酰胺代替苯甲酸作为底物时，也观察到了良好的催化活性。
• Synthesis of Isocoumarin Derivatives via the Copper-Catalyzed Tandem Sequential Cyclization of 2- Halo-<i>N</i>-phenyl Benzamides and Acyclic 1,3-Diketones
  作者：Veerababurao Kavala、Cheng-Chuan Wang、Deepak Kumar Barange、Chun-Wei Kuo、Po-Min Lei、Ching-Fa Yao

  DOI：10.1021/jo300501j

  日期：2012.6.1

  A facile and rapid synthesis of isocoumarin derivatives using a copper-catalyzed tandem C–C/C–O coupling strategy from readily available substrates is described. The reactions of a wide range of 2-iodo-N-phenyl benzamides and acyclic diketones as starting materials were investigated.

  本文描述了一种利用铜催化的串联式C–C / C–O偶联策略从容易获得的底物中轻松快速合成异香豆素衍生物的方法。研究了各种2-碘-N-苯基苯甲酰胺和无环二酮作为起始原料的反应。
• Synthetic and Computational Studies on Rh^III-Catalyzed Redox-Neutral Cascade of Carbenoid Functionalization and Dephosphonylative Annulation
  作者：Suvankar Bera、Partha Mondal、Debabrata Sarkar、Vijay Babu Pathi、Sourav Pakrashy、Ayan Datta、Biswadip Banerji

  DOI：10.1021/acs.joc.1c00311

  日期：2021.5.21

  A Rh(III)-catalyzed regioselective redox-neutral cascade process of carbenoid functionalization followed by dephosphonylative annulation of benzoic acids with α-diazo-β-keto phosphonate has been realized, which led to the direct synthesis of a privileged 3-substituted isocoumarin scaffold. To the best of our knowledge, this is the first report of a complete redox neutral method to synthesize isocoumarins

  已经实现了Rh（III）催化的类胡萝卜素官能团的区域选择性氧化还原中性级联过程，然后用α-重氮-β-酮膦酸酯对苯甲酸进行去膦酰基化环化反应，从而直接合成了优先的3-取代的异香豆素骨架。 。据我们所知，这是使用CHH功能化策略合成异香豆素的完整氧化还原中性方法的首次报道。在此反应的催化循环中，苯甲酸的原位碳原子与重氮碳原子之间存在C–C偶联的两种可能途径：（i）协同1,2-芳基转移和（ii）逐步金属–卡宾形成，然后迁移插入。DFT研究预测，与逐步途径相比，协同途径的活化能更低，为1.5 kcal / mol。
• Aryl iodine-catalysed divergent synthesis of isobenzofuranones and isocoumarins <i>via</i> oxidative 1,2-aryl migration/elimination
  作者：Jiaxin He、Jingran Zhang、Xuemin Li、Haofeng Shi、Yunfei Du

  DOI：10.1039/d2cc03101a

  日期：——

  The divergent synthesis of isobenzofuranones and isocoumarins was realized from the reaction of 2-alkenyl benzoic acids and mCPBA in the presence of catalytic aryl iodine and (±)-10-camphorsulfonic acid (CSA). The organocatalytic oxidative reaction is assumed to undergo a cascade process involving lactonization, 1,2-aryl migration and elimination enabled by a modified Koser reagent generated in situ

  在催化芳基碘和 (±)-10-樟脑磺酸 (CSA) 存在下，2-烯基苯甲酸和m CPBA 反应实现了异苯并呋喃酮和异香豆素的不同合成。假设有机催化氧化反应经历了一个级联过程，包括内酯化、1,2-芳基迁移和由原位产生的改性 Koser 试剂实现的消除。