3,3-difluoro-5-methoxy-1-methylindolin-2-one | 1239497-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,3-difluoro-5-methoxy-1-methylindolin-2-one
• 英文别名: 1-Methyl-3,3-difluoro-5-methoxy-1H-indole-2(3H)-one；3,3-difluoro-5-methoxy-1-methylindol-2-one
• CAS: 1239497-60-9
• 化学式: C₁₀H₉F₂NO₂
• 分子量: 213.184
• InChiKey: MHCQDOPFGOMRFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲基-P-氨基苯甲醚 在 dipotassium hydrogenphosphate 、 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 36.0h， 生成 3,3-difluoro-5-methoxy-1-methylindolin-2-one
  参考文献：
  名称：

  Visible-light photoredox intramolecular difluoroacetamidation: facile synthesis of 3,3-difluoro-2-oxindoles from bromodifluoroacetamides

  摘要：

  已经通过可见光照射下的分子内氨基羰基二氟甲基自由基加成到芳烃的方式高效合成了3,3-二氟-2-氧代吲哚。

  DOI：

  10.1039/c5ob02121a

文献信息

• 一种3,3-二氟-2-氧化吲哚衍生物的合成方法
  申请人：河南工程学院

  公开号：CN105367481B

  公开（公告）日：2018-08-17

  本发明属于医药化工合成技术领域，具体公开了一种3,3‑二氟‑2‑氧化吲哚衍生物的合成方法。首先选择不同的芳香胺与二氟溴乙酸的酯类生成芳香酰胺化合物；然后用卤代烃与该芳香酰胺化合物回流反应，得到N‑烷基保护的芳香酰胺化合物；然后添加促进剂和有机溶剂于50‑100℃反应6‑10小时，合成3,3‑二氟‑2‑氧化吲哚衍生物。本发明采用的合成方法操作简便，不使用任何金属，成本非常低，条件温和，转化率高，所用原料易得，价格低廉，适合于工业化生产的应用。
• Divergent Regioselective Csp²–H Difluoromethylation of Aromatic Amines Enabled by Nickel Catalysis
  作者：Quan Gou、Qianqiong Chen、Qiujian Tan、Minghong Zhu、Huisheng Huang、Mengjiao Deng、Wei Yi、Shuhua He

  DOI：10.1021/acs.orglett.2c01262

  日期：2022.5.20

  bidentate phosphine ligand, offering an invaluable synthesis means to construct extensive p-difluoromethylated products and difluorooxindole derivatives with significant functional fragments. Furthermore, the gram-scale reaction, broad substrate scope, excellent functional-group compatibility, late-stage difluoromethylation of pesticides, and even formal synthesis of HDAC6 inhibitors further demonstrate the

  在此，在二齿膦配体的帮助下，开发了第一个用于镍催化的各种芳族胺的邻位或对位二氟甲基化的催化方案，为构建广泛的对二氟甲基化产物和具有重要功能片段的二氟羟吲哚衍生物提供了宝贵的合成方法。 . 此外，克级反应、广泛的底物范围、优异的官能团相容性、农药的后期二氟甲基化，甚至HDAC6抑制剂的正式合成进一步证明了该方法的实用性。
• Copper-Mediated Fluoroalkylation Reactions with Iododifluoroacetamides: Controlling the Selectivity among Cross-Coupling, Intramolecular Cyclization, and Homocoupling Reactions
  作者：Jieming Zhu、Wei Zhang、Laijun Zhang、Jun Liu、Ji Zheng、Jinbo Hu

  DOI：10.1021/jo1005262

  日期：2010.8.20

  Cu-mediated fluoroalkylation reactions with iododifluoroacetamides I have been systematically investigated. It was found that three types of reactions may coexist in Cu-mediated reactions between iododifluoroacetamides and aryl/alkenyl iodides: cross-coupling, intramolecular cyclization, and homocoupling reactions. The selectivity among these three types of reactions could be controlled by tuning the substituents on the nitrogen atom of iododifluoroacetamides, and/or by removing the cross-coupling reaction partner (aryl/alkenyl halides). The general rule is as follows: (a) in the presence of proper aryl/alkenyl iodides, the cross-coupling products 2 (or 6) are generally formed as the major products; (b) in the absence of aryl/alkenyl iodides, and when R-1 = alkyl and R-2 = aryl groups, or when R-1 = R-2 = aryl groups, the intramolecular cyclization products 3 can be formed predominantly; and (c) in the absence of aryl/alkenyl iodides, and when R-1 = R-2 = alkyl groups, or when R-1 = H and R-2 = alkyl, aryl groups, the homocoupling products 4 can be formed dominantly. Our experimental results also indicate that in many cases when cross-coupling, homocoupling, and intramolecular cyclization reactions coexist in the Cu-mediated reaction system, the reactivity decreases in the following order: cross-coupling > intramolecular cyclization > homocoupling.