2-(p-methoxybenzyl)-3-methylisoindolin-1-one | 206977-07-3

• 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: 2-(p-methoxybenzyl)-3-methylisoindolin-1-one
• 英文别名: 2-(4-methoxy-benzyl)-3-methyl-2,3-dihydro-isoindol-1-one；2-[(4-methoxyphenyl)methyl]-3-methyl-3H-isoindol-1-one
• CAS: 206977-07-3
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: FUBZBJAZTACMJP-UHFFFAOYSA-N

物化性质

• 沸点：
  430.1±45.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(p-methoxybenzyl)-3-methylisoindolin-1-one 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以82%的产率得到2-(4-Methoxy-benzyl)-1-methyl-2,3-dihydro-1H-isoindole
  参考文献：
  名称：

  LDA-induced metalation of isoindolinones. An efficient route to 3-substituted isoindoline derivatives

  摘要：

  3-Substituted isoindolines have been efficiently prepared by sequential lithiation and reduction of isoindolinones. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00136-1
• 作为产物：
  描述：

  3-Benzenesulfonyl-2-(4-methoxy-benzyl)-3-methyl-2,3-dihydro-isoindol-1-one 在 镍 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 2-(p-methoxybenzyl)-3-methylisoindolin-1-one
  参考文献：
  名称：

  Alkylation and annulation of 3-(phenylsulfonyl)-2-alkyl-2,3-dihydroisoindol-1-ones

  摘要：

  The hydroxylactams obtained from reduction of N-substituted phthalimides were phenylthiated and oxidized to give 3-(phenylsulfonyl)-2,3-dihydroisoindol-1-ones Deprotonation of the sulfones with sodium hydride followed by treatment with electrophiles gave substitution. Sulfones with suitably-disposed alpha,beta-unsaturated ester groups gave cyclic products from intramolecular Michael addition. Desulfurization of the phenylsulfonyl intermediates was effected in quantitative yield using Raney nickel promoted by ultrasound. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00293-7

文献信息

• Hydrogenolysis of the C-O bond of hydroxylactams as a convenient method for the synthesis of substituted isoindolin-1-ones
  作者：Zh. R. Sagirova、E. V. Starodubtseva、O. V. Turova、M. G. Vinogradov

  DOI：10.1007/s11172-013-0137-7

  日期：2013.4

  A simple and efficient method for the synthesis of isoindolin-1-ones containing alkyl or aryl substituents at positions 2 and (or) 3 was suggested. The method is based on the earlier unknown Pd0-catalyzed hydrogenolysis of hydroxylactams.

  提出了一种简单高效的方法，用于合成在2位和（或）3位含有烷基或芳基取代基的异吲哚-1-酮。该方法基于之前未知的Pd0催化的氢解羟基内酰胺反应。
• Novel Chemoselective Desulfurization of γ-Phenylthio-Substituted Aromatic Lactams: Application to the Synthesis of Isoindolobenzazepine Alkaloid, Lennoxamine
  作者：Hidemi Yoda、Takamasa Suzuki、Kunihiko Takabe

  DOI：10.1055/s-2006-956452

  日期：2006.12

  Treatment of a variety of γ-phenylthio-substituted aromatic lactams with lithium aluminum hydride in the presence of cuprous iodide led to novel chemoselective desulfurization reactions to afford the corresponding substituted aromatic lactams without giving the carbonyl-reduced and/or ring-opened products in extremely high yields. This process was further applied to the total synthesis of an isoindolobenzazepine alkaloid, lennoxamine, by featuring the elaboration of the functionalized phthalimide derivative.

  在碘化亚铜存在下，用氢化铝锂处理各种δ-苯硫基取代的芳香族内酰胺，可产生新的化学选择性脱硫反应，从而得到相应的取代芳香族内酰胺，且不产生羰基还原和/或开环产物，收率极高。这一工艺还被进一步应用于异吲哚苯并氮杂卓生物碱--伦诺沙明的全合成，其特点是可以制备功能化邻苯二甲酰亚胺衍生物。
• ANDERSON P. S.; CHRISTY M. E.; COLTON C. D.; HALCZENKO W.; PONTICELLO G. +, J. ORG. CHEM., 1979, 44, NO 9, 1519-1533
  作者：ANDERSON P. S.、 CHRISTY M. E.、 COLTON C. D.、 HALCZENKO W.、 PONTICELLO G. +

  DOI：——

  日期：——