(E)-N-(p-methoxyphenylmethyl)-3-(p-methoxyphenylmethylidene)isoindolin-1-one | 1209455-83-3

• 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: (E)-N-(p-methoxyphenylmethyl)-3-(p-methoxyphenylmethylidene)isoindolin-1-one
• 英文别名: (3E)-2-[(4-methoxyphenyl)methyl]-3-[(4-methoxyphenyl)methylidene]isoindol-1-one
• CAS: 1209455-83-3
• 化学式: C₂₄H₂₁NO₃
• 分子量: 371.436
• InChiKey: QRUCWDFNHNVLEE-HZHRSRAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻羧基苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 6.75h， 生成 (Z)-N-(p-methoxyphenylmethyl)-3-(p-methoxyphenylmethylidene)isoindolin-1-one 、 (E)-N-(p-methoxyphenylmethyl)-3-(p-methoxyphenylmethylidene)isoindolin-1-one
  参考文献：
  名称：

  Practical and high stereoselective synthesis of 3-(arylmethylene)isoindolin-1-ones from 2-formylbenzoic acid

  摘要：

  Practical and high stereoselective synthesis of 3-(arylmethylene)isoindolin-1-ones is reported. The synthetic method involves the preparation of dimethyl isoindolin-1-one-3-yl-phosphonates by a 'one-pot' three-component reaction of 2-formylbenzoic acid with 4-methoxybenzylamine or aminoacetaldehyde dimethyl acetal and dimethyl phosphite under solvent and catalyst free-conditions, followed by a Horner reaction with several aryl aldehydes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.040

文献信息

• Dichotomous Control of<i>E</i>/<i>Z</i>-Geometry in Intramolecular Cyclization of<i>o</i>-Alkynylbenzamide Derivatives Catalyzed by Organic Superbase P4-<i>t</i>Bu in the Presence/Absence of Water
  作者：Chikashi Kanazawa、Masahiro Terada

  DOI：10.1002/asia.200900342

  日期：2009.11.2

  it! An intramolecular cyclization reaction of o‐alkynylbenzamides that allows dichotomous control of E/Z‐geometry has been developed using an organic superbase, P4‐tBu, as a catalyst. The presence/absence of water along with the use of an organic superbase provides the necessary control of the geometry at the exo‐double bond. The method enables efficient access to isoindolinone derivatives, an important

  E / Z 做到了！邻炔基苯甲酰胺的分子内环化反应可实现E / Z几何形状的二分控制，已使用有机超碱P4- t Bu作为催化剂进行了开发。水的存在与否以及有机超碱的使用为exo- double键的几何形状提供了必要的控制。该方法能够有效利用异吲哚啉酮衍生物，这是一类重要的生物活性分子。
• Practical and high stereoselective synthesis of 3-(arylmethylene)isoindolin-1-ones from 2-formylbenzoic acid
  作者：Miguel Angel Reyes-González、Angel Zamudio-Medina、Mario Ordóñez

  DOI：10.1016/j.tetlet.2012.08.040

  日期：2012.10

  Practical and high stereoselective synthesis of 3-(arylmethylene)isoindolin-1-ones is reported. The synthetic method involves the preparation of dimethyl isoindolin-1-one-3-yl-phosphonates by a 'one-pot' three-component reaction of 2-formylbenzoic acid with 4-methoxybenzylamine or aminoacetaldehyde dimethyl acetal and dimethyl phosphite under solvent and catalyst free-conditions, followed by a Horner reaction with several aryl aldehydes. (C) 2012 Elsevier Ltd. All rights reserved.