1-methyl-2-phenylisoindoline | 141636-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1-methyl-2-phenylisoindoline
• 英文别名: 1-Methyl-2-phenyl-1,3-dihydroisoindole
• CAS: 141636-34-2
• 化学式: C₁₅H₁₅N
• 分子量: 209.291
• InChiKey: DQUBIABUHYJJMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-溴-N-(1-苯基乙基)苯胺 在 bis(η3-allyl-μ-chloropalladium(II)) 、 caesium carbonate 、 溶剂黄146 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 、 cesium pivalate 作用下， 以 间二甲苯 为溶剂， 反应 17.08h， 生成 1-methyl-2-phenylisoindoline
  参考文献：
  名称：

  Remote Construction of N‐Heterocycles via 1,4‐Palladium Shift‐Mediated Double C−H Activation

  摘要：

  AbstractIn the past years, Pd0‐catalyzed C(sp3)−H activation provided efficient and step‐economical methods to synthesize carbo‐ and heterocycles via direct C(sp2)−C(sp3) bond formation. We report herein that a 1,4‐Pd shift allows access to N‐heterocycles which are difficult to build via a direct reaction. It is shown thato‐bromo‐N‐methylanilines undergo a 1,4‐Pd shift at theN‐methyl group, followed by intramolecular trapping by C(sp2)−H or C(sp3)−H activation at another nitrogen substituent and remote C−C bond formation to generate biologically relevant isoindolines and β‐lactams. The product selectivity is influenced by the employed ligand, with NHCs favoring the product of remote C−C coupling against products arising from direct C−C coupling and N‐demethylation.

  DOI：

  10.1002/anie.202116101

文献信息

• Stoichiometric and Catalytic Inter- and Intramolecular Hydroamination of Terminal Alkynes by Frustrated Lewis Pairs
  作者：Tayseer Mahdi、Douglas W. Stephan

  DOI：10.1002/chem.201501535

  日期：2015.7.27

  Frustrated Lewis pairs (FLPs) based on sterically encumbered anilines and the Lewis acid B(C6F5)3 were found to react with terminal alkynes effecting intermolecular hydroamination affording iminium alkynylborate species of the form [RPhNC(R′)Me][R′CCB(C6F5)3]. In these cases, the reagent ratio of borane, aniline, and alkyne is 1:1:2. These reactions could also be performed in an intramolecular fashion

  发现基于位阻苯胺的沮丧的路易斯对（FLP）和路易斯酸B（C 6 F 5）3与末端炔烃反应，进行分子间加氢胺化反应，从而提供[RPhNC（R'）Me]形式的炔基硼酸亚胺盐。 [R'CCB（C 6 F 5）3 ]。在这些情况下，硼烷，苯胺和炔烃的试剂比为1：1：2。这些反应也可以以分子内方式通过使用具有炔基取代基的苯胺来实现环化反应来进行。在H 2气氛下使用10 mol％B（C 6 F 5）3提供吡咯烷的一锅合成12，是哌啶13 - 15，所述氮杂环庚烷16，异吲哚啉17，和苯并恶嗪18。
• Cobalt‐Catalyzed Selective Transformation of Levulinic Acid and Amines into Pyrrolidines and Pyrrolidinones using Hydrogen
  作者：Yixiao Pan、Zhenli Luo、Ji Yang、Jiahong Han、Jianbo Yang、Zhen Yao、Lijin Xu、Peng Wang、Qian Shi

  DOI：10.1002/adsc.202200578

  日期：2022.8.16

  Cobalt-catalyzed selective transformation of levulinic acid and primary amines into pyrrolidines and pyrrolidinones under H2 has been developed. The catalyst system consisting of Co(NTf2)2, 1,1,1-tris(di(4-methoxyphenyl)phosphinomethyl) ethane ((p-anisyl)triphos) and Me3SiOTf works well for the synthesis of pyrrolidines via reductive amination/cyclization/deoxygenative reduction of amide, and using Co(NTf2)2/1

  已经开发了在 H 2下钴催化的乙酰丙酸和伯胺选择性转化为吡咯烷和吡咯烷酮。由Co(NTf 2 ) 2、1,1,1-三(二(4-甲氧基苯基)膦甲基)乙烷((对茴香基)三膦)和Me 3 SiOTf组成的催化剂体系适用于通过还原反应合成吡咯烷酰胺的胺化/环化/脱氧还原，并使用Co(NTf 2 ) 21,1,1-三(二苯基膦基甲基)乙烷(triphos)在氢气减压下作为催化剂导致仅形成吡咯烷酮。芳基和烷基伯胺都是合适的底物，并且可以容忍多种官能团。同时，4-氧代-4-芳基丁酸、5-氧代己酸、6-氧代庚酸、2-甲酰基苯甲酸、2-乙酰基苯甲酸和2'-乙酰基-[1,1'-联苯]-2-羧酸是也适用，允许方便地获得具有不同环大小的环胺和内酰胺。
• Wittig et al., Justus Liebigs Annalen der Chemie, 1955, vol. 594, p. 89,111
  作者：Wittig et al.

  DOI：——

  日期：——
• Photoreactions of isoindoline-1-thiones with alkenes: unusual formation of tricyclic isoindolines
  作者：Takehiko Nishio、Norikazu Okuda

  DOI：10.1021/jo00040a049

  日期：1992.7

  Photochemical cycloaddition reactions of cyclic thioamides and alkenes have been examined. Irradiation of 2-arylisoindoline-1-thiones 1 in the presence of alkenes 2 gave the unexpected tricyclic isoindolines 3-18. The formation of tricyclic isoindolines can best be explained in terms of the intermediacy of aminospirothietane 27, formed by [2 + 2] photocycloaddition of the C=S double bond of 1 to the C=C double bond of 2. Ring cleavage of the resultant amino thietane, assisted by the participation of the nitrogen lone-pair electrons, produced zwitterions 28 and 29 or 1-mercaptoethylisoindole (30). Subsequent nucleophilic attack of the thiol anion on the iminium carbon of 29 or attack of the thiol group on C-3 of 30 gave the final products. Irradiation of isobenzofuran-1-thione (22) and isobenzothiophene-l-thione (23) in the presence of tetramethylethylene (2a) gave the corresponding spirothietanes 24 and 25.