6-chloro-3-methylisobenzofuran-1(3H)-one | 118343-30-9

• 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: 6-chloro-3-methylisobenzofuran-1(3H)-one
• 英文别名: 6-chloro-3-methyl-3H-2-benzofuran-1-one
• CAS: 118343-30-9
• 化学式: C₉H₇ClO₂
• 分子量: 182.606
• InChiKey: ZLEHRGKHQMVTOX-UHFFFAOYSA-N

物化性质

• 熔点：
  121-123 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  316.1±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)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-3-methylisobenzofuran-1(3H)-one 在 乙醇 、 一水合肼 作用下， 生成 5-chloro-2-(1-hydroxy-ethyl)-benzoic acid hydrazide
  参考文献：
  名称：

  Teppema, Recueil des Travaux Chimiques des Pays-Bas, 1923, vol. 42, p. 37

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-氨基-4-氯苯基)乙酮 在 盐酸 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 50.58h， 生成 6-chloro-3-methylisobenzofuran-1(3H)-one
  参考文献：
  名称：

  Highly Stereoselective Chemoenzymatic Synthesis of the 3H-Isobenzofuran Skeleton. Access to Enantiopure 3-Methylphthalides

  摘要：

  A straightforward synthesis of (S)-3-methylphthalides has been developed, with the key asymmetric step being the bioreduction of 2-acetylbenzonitriles. Enzymatic processes have been found to be highly dependent on the pH value, with acidic conditions being required to avoid undesired side reactions. Baker's yeast was found lobe the best biocatalyst acting in a highly stereoselective fashion. The simple treatment of the reaction crudes with aqueous HCl has provided access to enantiopure (S)-3-methylphthalides in moderate to excellent yields.

  DOI：

  10.1021/ol300191s

文献信息

• Incorporation of carbon dioxide into phthalides via ligand-free copper-catalyzed direct carboxylation of benzoxasiloles
  作者：Thanh V. Q. Nguyen、José A. Rodríguez-Santamaría、Woo-Jin Yoo、Shū Kobayashi

  DOI：10.1039/c7gc00917h

  日期：——

  The direct carboxylation of benzoxasiloles with carbon dioxide proceeded smoothly under mild conditions using copper iodide as a catalyst to afford phthalides after an acid work-up. Broad substrate scope and application of this methodology for the synthesis of natural products highlight the synthetic utility of this protocol.

  在弱酸条件下，使用碘化铜作为催化剂，在温和的条件下，苯并二甲酚与二氧化碳的直接羧化反应顺利进行，从而在酸处理后得到邻苯二甲酸盐。该方法在天然产物合成中的广泛底物范围和应用突出了该方案的合成效用。
• Ruthenium-Catalyzed Enantioselective Hydrogenation/Lactonization of 2-Acylarylcarboxylates: Direct Access to Chiral 3-Substituted Phthalides
  作者：Bin Lu、Mengmeng Zhao、Guangni Ding、Xiaomin Xie、Lili Jiang、Virginie Ratovelomanana-Vidal、Zhaoguo Zhang

  DOI：10.1002/cctc.201700695

  日期：2017.10.23

  Synthesis of synthons: The asymmetric hydrogenation and subsequent in situ lactonization with Ru-diphosphines results in the direct conversion of a series of 2-acylarylcarboxylates including 2-aroylarylcarboxylates into the corresponding optically active 3-substituted phthalides under mild reaction conditions.

  合成子的合成：不对称氢化和随后用Ru-二膦进行原位内酯化可在温和的反应条件下将包括2-芳基芳基羧酸盐在内的一系列2-酰基芳基羧酸盐直接转化为相应的光学活性3-取代的邻苯二甲酸酯。
• Hydroiodination-Triggered Cascade Reaction with I₂ /PPh₃ /H₂ O: Metal-Free Access to 3-Substituted Phthalides from 2-Alkynylbenzoates
  作者：Shin-ichi Kawaguchi、Kentaro Nakamura、Kotaro Yamaguchi、Yuki Sato、Yuhei Gonda、Masaaki Nishioka、Motohiro Sonoda、Akihiro Nomoto、Akiya Ogawa

  DOI：10.1002/ejoc.201700839

  日期：2017.10.2

  synthesis of phthalides are strongly desired. Herein, we describe the metal-free synthesis of 3-substituted phthalides by the reductive hydroiodination of 2-alkynylbenzoates through an I2/PPh3/H2O-triggered cascade reaction. A variety of 3-substituted phthalides were synthesized in excellent yields by a one-pot reaction involving four processes: desilylation, hydroiodination, cyclization, and reduction.

  邻苯二甲酰胺是在几种生物活性化合物中发现的重要支架。因此，强烈需要有效的合成邻苯二甲酰亚胺的方法。在这里，我们描述了通过I 2 / PPh 3 / H 2 O引发的级联反应，通过2-炔基苯甲酸酯的还原性加氢碘化反应，合成了无金属的3-取代的邻苯二甲酸酯。通过一锅法反应，涉及四个过程：去甲硅烷基化，加氢碘化，环化和还原反应，以优异的产率合成了多种3-取代的邻苯二甲酸酯。
• Lewis Acid-assisted Dirhodium(II)-catalyzed Ketone Hydroacylation
  作者：Tomohiro Yasukawa、Shū Kobayashi

  DOI：10.1246/cl.160862

  日期：2017.1.5

  Rh(II) salt and a Lewis acid, Sc(OTf)3, as a highly active and robust cooperative catalyst system for ketone hydroacylation was developed. The catalyst system showed high turnover numbers (up to ca. 400) even under air, whereas the corresponding Rh(I)/Sc(OTf)3 system did not work well. The application of the Rh(II)/Sc system was also extended to hydroacylation of olefins and an enantioselective reaction

  开发了 Rh(II) 盐和路易斯酸 Sc(OTf)3 的组合，作为用于酮加氢酰化的高活性和稳健的协同催化剂体系。即使在空气中，催化剂体系也显示出高周转数（高达约 400），而相应的 Rh(I)/Sc(OTf)3 体系效果不佳。Rh(II)/Sc 体系的应用还扩展到烯烃的加氢酰化和对映选择性反应。
• Iron/photoredox dual catalysis for acyl nitrene-based C–O bond formation towards phthalides
  作者：Zhide Zhang、Yangling Deng、Ming Hou、Xiaojing Lai、Meng Guan、Fengzhi Zhang、Rui Qi、Guanyinsheng Qiu

  DOI：10.1039/d2cc04917a

  日期：——

  iron/photoredox dual-catalyzed acyl nitrene formation and the use of acyl nitrene in constructing various C–O bonds towards phthalides. The developed reaction starts from N-methoxyl-2-alkylbenzamides. Mechanism surveys suggest the reaction involves iron nitrene-based hydrogen atom abstraction (HAA), radical-polar crossover and O-nucleophilic SN1. Distinctively, the often-reported radical rebound in previous publications

  本文描述了铁/光氧化还原双催化酰基氮烯的形成以及酰基氮烯在构建各种 C-O 键中对苯酞的应用。开发的反应从N -methoxyl-2-alkylbenzamides 开始。机理调查表明，该反应涉及基于铁氮烯的氢原子提取 (HAA)、自由基-极性交叉和O-亲核 S N 1。值得注意的是，未观察到以前出版物中经常报道的自由基反弹。该反应代表了基于酰基氮烯的苯酞合成的第一个例子。此外，它还作为合成3-丁基苯酞（NBP）、沙利度胺、Pomalyst和Otezia等市售药物的补充剂。