6-methyl-2-phenylisoindolin-1-one | 33886-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 6-methyl-2-phenylisoindolin-1-one
• 英文别名: 6-methyl-2-phenyl-3H-isoindol-1-one
• CAS: 33886-51-0
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: FPMLRRXBJXCJIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  189-191 °C
• 沸点：
  403.5±45.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 aluminum (III) chloride 、 sodium tetrahydroborate 、 1,2-双[(2R,5R)-2,5-二乙基磷杂环戊烷基]苯(1,5-环辛二烯)铑(I)四氟硼酸盐 、 溶剂黄146 、 N,N-二异丙基乙胺 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 6-methyl-2-phenylisoindolin-1-one
  参考文献：
  名称：

  Direct Access to Benzolactams and Benzolactones via Nickel Catalyzed Carbonylation with CO2

  摘要：

  A new nickel catalyzed cross‐electrophile coupling for accessing γ‐lactams (isoindolinones) as well as γ‐lactones (isobenzofuranones) via carbonylation with CO2 is documented. The protocol exploits the synergistic role of redox‐active Ni(II) complexes and AlCl3 as a CO2 activator/oxygen scavenger, leading to the formation of a wide range of cyclic amides and esters (28 examples) in good to high yields (up to 87%). A dedicated computational investigation revealed the multiple roles played by AlCl3. In particular, the simultaneous transient protection of the pendant amino group of the starting reagents and the formation of the electrophilically activated CO2‐AlCl3 adduct are shown to concur in paving the way for an energetically favorable mechanistic pathway.

  DOI：

  10.1002/chem.202401658

文献信息

• Metal-Free Cascade Formation of Intermolecular C–N Bonds Accessing Substituted Isoindolinones under Cathodic Reduction
  作者：Zirong Zou、Genuo Cai、Weihao Chen、Canlin Zou、Yamei Li、Hongting Wu、Lu Chen、Jinhui Hu、Yibiao Li、Yubing Huang

  DOI：10.1021/acs.joc.1c01845

  日期：2021.11.5

  An electrochemical protocol for the construction of substituted isoindolinones via reduction/amidation of 2-carboxybenzaldehydes and amines has been realized. Under metal-free and external-reductant-free electrolytic conditions, the reaction achieves the cascade formation of intermolecular C–N bonds and provides a series of isoindolinones in moderate to good yields. The deuterium-labeling experiment

  已经实现了通过 2-羧基苯甲醛和胺的还原/酰胺化来构建取代异吲哚啉酮的电化学方案。在无金属和无外部还原剂的电解条件下，该反应实现了分子间 C-N 键的级联形成，并以中等至良好的产率提供了一系列异吲哚啉酮。氘标记实验证明，产物亚甲基中的氢主要由体系中的H 2 O提供。
• Transition metal free intramolecular selective oxidative C(sp³)–N coupling: synthesis of N-aryl-isoindolinones from 2-alkylbenzamides
  作者：Ajay Verma、Saket Patel、Meenakshi Meenakshi、Amit Kumar、Abhimanyu Yadav、Shailesh Kumar、Sadhan Jana、Shubham Sharma、Ch. Durga Prasad、Sangit Kumar

  DOI：10.1039/c4cc08717h

  日期：——

  isoindolinones including indoprofen and DWP205190 drugs from 2-alkylbenzamide substrates by transition metal-free intramolecular selective oxidative coupling of C(sp(3))-H and N-H bonds utilizing iodine, potassium carbonate and di-tert-butyl peroxide in acetonitrile at 110-140 degrees C.

  通过使用碘，碳酸钾通过C（sp（3））-H和NH键的无过渡金属的分子内选择性氧化偶联，已开发出一种用于从2-烷基苯甲酰胺底物制备生物学上重要的异吲哚啉酮（包括吲哚洛芬和DWP205190药物）的合成方法和二叔丁基过氧化物的乙腈溶液，温度为110-140摄氏度。
• Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams
  作者：Ya Bai、Lingling Shi、Lianyou Zheng、Shulin Ning、Xin Che、Zhuoqi Zhang、Jinbao Xiang

  DOI：10.1021/acs.orglett.1c00430

  日期：2021.3.19

  and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group

  已经开发了一种使用室温下带有碳电极的简单的不分隔电池来选择性还原环状酰亚胺的高效实用的电化学方法。该反应为通过控制电流和反应时间调节的可控方式快速合成羟基内酰胺和内酰胺提供了有用的策略，并且具有宽泛的底物范围和对还原敏感部分的高官能团耐受性。最初的机械研究表明，该方法在很大程度上依赖于能够生成α-氨基烷基自由基的胺（例如i- Pr 2 NH）的利用。该方案为在温和条件下以高化学选择性裂解C–O键提供了一条有效途径。
• Isoindolinone Synthesis: Selective Dioxane-Mediated Aerobic Oxidation of Isoindolines
  作者：Pawan Thapa、Esai Corral、Sinjinee Sardar、Brad S. Pierce、Frank W. Foss

  DOI：10.1021/acs.joc.8b01920

  日期：2019.1.18

  N-Alkyl and N-aryl-isoindolinones were prepared by a dioxane-mediated oxidation of isoindoline precursors. The transformation exhibits unique chemoselectivity for isoindonlines. A chiral tertiary (3°)-benzylic position was not racemized during oxidation, and methyl indoprofen was prepared by late stage oxidation. Mechanistic studies suggest a selective H atom transfer, which avoids many known oxidation (by-)products

  N-烷基和N-芳基-异吲哚啉酮是通过二恶烷介导的异吲哚啉前体的氧化反应制备的。该转化表现出对异茚满碱独特的化学选择性。在氧化过程中手性叔（3°）-苄基位置未消旋，通过后期氧化制备了甲基吲哚洛芬。机理研究表明，选择性的H原子转移可避免许多已知的异吲哚啉酮氧化（副）产物。
• Opening of the epoxide bridge in 3a,6-epoxyisoindol-1-ones by the action of BF3⋅Et2O in acetic anhydride*
  作者：F. I. Zubkov、V. P. Zaytsev、E. S. Puzikova、E. V. Nikitina、V. N. Khrustalev、R. A. Novikov、A. V. Varlamov

  DOI：10.1007/s10593-012-1024-0

  日期：2012.6

  epoxide bridge in N-substituted 2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1-ones by the action of BF3⋅Et2O in acetic anhydride at 25°C over 1 h proceeds through an SN1 mechanism. The allylic type cation formed in the first step is stabilized by the addition of an acetoxy group at C-5 in the isoindole system to give a mixture of cis and trans isomers of 5,6-diacetoxy-2,3,5,6,7,7a-hexa-hydroisoindol-1-ones, which

  在25°C下于1小时内通过BF 3· Et 2 O在乙酸酐中的作用进行N-取代的2,3,7,7a-四氢-3a，6-环氧异吲哚-1-酮中的环氧基桥的反应通过S N 1机制。在第一步中形成的烯丙基型阳离子可通过在异吲哚体系中的C-5处添加乙酰氧基来稳定，得到5,6-二乙酰氧基-2,3,5,6的顺式和反式异构体的混合物，将7，7a-六氢异吲哚-1-酮在这些条件下经24小时芳构化，得到2，3-二氢-1H-异吲哚-1-酮。