3,7-dimethylisobenzofuran-1(3H)-one | 1363507-56-5

• 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: 3,7-dimethylisobenzofuran-1(3H)-one
• 英文别名: 3,7-dimethyl-3H-2-benzofuran-1-one
• CAS: 1363507-56-5
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: LNZOYSNNFJTWLH-UHFFFAOYSA-N

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：
  0.3
• 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：

  1-(2-氨基-3-甲基苯基)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 3,7-dimethylisobenzofuran-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

• 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。
• Pyrimidines as PLK inhibitors
  申请人：STADTMUELLER Heinz

  公开号：US20110086842A1

  公开（公告）日：2011-04-14

  The present invention encompasses compounds of general formula (1), wherein A, W, X, Y, Z, Ra, Rb, Rc, R1 and R3 are defined as in claim 1 , which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and the use thereof for preparing a pharmaceutical composition having the above-mentioned properties.

  本发明涵盖了一般式（1）的化合物，其中A、W、X、Y、Z、Ra、Rb、Rc、R1和R3如权利要求1所定义，适用于治疗以细胞过度或异常增殖为特征的疾病，并且用于制备具有上述特性的药物组合物。
• 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。
• US7521457B2
  申请人：——

  公开号：US7521457B2

  公开（公告）日：2009-04-21
• Highly Stereoselective Chemoenzymatic Synthesis of the 3<i>H</i>-Isobenzofuran Skeleton. Access to Enantiopure 3-Methylphthalides
  作者：Juan Mangas-Sánchez、Eduardo Busto、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1021/ol300191s

  日期：2012.3.16

  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.