2-(dimethylamino)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one | 287199-38-6

• 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-(dimethylamino)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one
• 英文别名: 2-(dimethylamino)-3-hydroxy-3H-isoindol-1-one
• CAS: 287199-38-6
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: PLEVTOOMOMYQKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 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：
  43.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(dimethylamino)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one 在 对甲苯磺酸 、 三氟乙酸 、 lithium hexamethyldisilazane 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 4.0h， 生成 3-甲基异-1-酮
  参考文献：
  名称：

  Synthesis of 3-alkyl-1-isoindolinones by alkylation of a benzotriazolyl substituted N-dimethylamino-phthalimidine

  摘要：

  A convenient and versatile synthesis of 3-alkyl-2,3-dihydro-1H-isoindol-1-ones (isoindolinones) based upon sequential metalation, alkylation alpha to nitrogen and C,N-deprotection from 3-benzotriazolyl-2-dimethylamino-phthalimidine is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00073-4
• 作为产物：
  描述：

  2-(二甲基氨基)异吲哚啉e-1,3-二酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以82%的产率得到2-(dimethylamino)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one
  参考文献：
  名称：

  Synthesis of 3-alkyl-1-isoindolinones by alkylation of a benzotriazolyl substituted N-dimethylamino-phthalimidine

  摘要：

  A convenient and versatile synthesis of 3-alkyl-2,3-dihydro-1H-isoindol-1-ones (isoindolinones) based upon sequential metalation, alkylation alpha to nitrogen and C,N-deprotection from 3-benzotriazolyl-2-dimethylamino-phthalimidine is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00073-4

文献信息

• A new and versatile synthetic route to 2-dimethylamino-3-alkyl and arylmethylene-2,3-dihydro-1H-isoindol-1-ones
  作者：Eric Deniau、Dieter Enders

  DOI：10.1016/s0040-4039(02)01972-x

  日期：2002.11

  A variety of 2-dimethylamino-3-alkyl and arylmethylene-2,3-dihydro-1H-isoindol-1-ones have been efficiently prepared from an appropriate 3-benzotriazolyl substituted parent model via a three-step sequence involving deprotonation, subsequent alkylation and ultimate elimination reaction induced by an acidic treatment.

  已经通过合适的3-苯并三唑基取代的母体模型通过涉及去质子化的三步顺序有效地制备了各种2-二甲基氨基-3-烷基和芳基亚甲基-2,3-二氢-1H-异吲哚-1-酮，随后酸处理引起的烷基化和最终消除反应。
• Dialkylhydrazides for directed orthometalations
  作者：Scott A Pratt、Michael P Goble、Michael J Mulvaney、Peter G.M Wuts

  DOI：10.1016/s0040-4039(00)00462-7

  日期：2000.5

  Dimethylhydrazides are shown to be excellent substrates for the directed orthometalation reaction. The advantage of using the hydrazide is that it is easily removed by treatment with H5IO6 or CuCl2 to give the carboxylic acid under very mild conditions, in contrast to other amides that generally require harshly acidic conditions to achieve hydrolysis. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of 3-alkyl-1-isoindolinones by alkylation of a benzotriazolyl substituted N-dimethylamino-phthalimidine
  作者：Eric Deniau、Dieter Enders

  DOI：10.1016/s0040-4020(01)00073-4

  日期：2001.3

  A convenient and versatile synthesis of 3-alkyl-2,3-dihydro-1H-isoindol-1-ones (isoindolinones) based upon sequential metalation, alkylation alpha to nitrogen and C,N-deprotection from 3-benzotriazolyl-2-dimethylamino-phthalimidine is described. (C) 2001 Elsevier Science Ltd. All rights reserved.