(Z)-2-(4-methoxybenzyl)-3-benzylideneisoindolin-1-one | 1086598-96-0

• 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: (Z)-2-(4-methoxybenzyl)-3-benzylideneisoindolin-1-one
• 英文别名: (Z)-3-benzylidene-2-(4-methoxybenzyl)isoindolin-1-one；3-benzylidene-2-(4-methoxybenzyl)isoindolin-1-one；(Z)-3-benzylidene-2-(4-methoxybenzyl)-2,3-dihydro-isoindol-1-one；(Z)-3-benzylidene-N-(p-methoxyphenylmethyl)isoindolin-1-one；(3Z)-3-benzylidene-2-[(4-methoxyphenyl)methyl]isoindol-1-one
• CAS: 1086598-96-0
• 化学式: C₂₃H₁₉NO₂
• 分子量: 341.409
• InChiKey: TZJQBJYEYQPITE-JCMHNJIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  (Z)-2-(4-methoxybenzyl)-3-benzylideneisoindolin-1-one 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到(Z)-3-benzylidene-2-(4-hydroxybenzyl)isoindolin-1-one
  参考文献：
  名称：

  偶发的一锅氰化/水解/酰胺形成：直接获得3-亚甲基异吲哚-1-酮。

  摘要：

  据报道，使用CuCN作为唯一试剂，可以在无水或无氧条件下直接将2'-卤代苯乙酮一次转化为3-亚甲基异吲哚-1-酮支架。这种偶然发现的具有宽泛底物范围的转化为这些重要的支架提供了截然不同的途径。该方法的范围也进一步扩展到了三种特殊支架的合成，这三种支架类似于各种生物活性药物。

  DOI：

  10.1002/chem.202003209
• 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)-2-(4-methoxybenzyl)-3-benzylideneisoindolin-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。
• Efficient Synthesis of a (Z)-3-Methyleneisoindolin-1-one Library Using Cu(OAc)2•H2O/DBU under Microwave Irradiation
  作者：Li Zhang、Yongliang Zhang、Xin Wang、Jingkang Shen

  DOI：10.3390/molecules18010654

  日期：——

  Microwave-promoted efficient synthesis of a (Z)-3-methyleneisoindolin-1-one library from 2-bromobenzamides and terminal alkynes using Cu(OAc)2•H2O/DBU is described. Various benzamide substituents, ring substitutions, including heteroaryl, aryl acetylenes and aliphatic alkynes, could be applied to afford the desired products in good to moderate yield with high stereoselectivity. It is noteworthy that DBU maybe play a dual role as not only the base, but also as a ligand for copper. The reaction is catalyzed by the complex of Cu(OAc)2•H2O and DBU without other additives.

  介绍了利用 Cu(OAc)2-H2O/DBU 以 2-溴苯甲酰胺和端炔类化合物为原料，通过微波促进高效合成 (Z)-3 亚甲基异吲哚啉-1-酮库。应用各种苯甲酰胺取代基、环取代基（包括杂芳基、芳基乙炔基和脂肪族炔烃）可得到所需的产品，产率从良好到中等，且具有很高的立体选择性。值得注意的是，DBU 可能具有双重作用，它不仅是碱，还是铜的配体。该反应由 Cu(OAc)2-H2O 和 DBU 的络合物催化，无需其他添加剂。
• 1,5,7‐Triazabicyclo[4.4.0]dec‐5‐ene (TBD): An Organocatalyst for Rapid Access to 3‐Hydroxyisoindolin‐1‐ones
  作者：Chunling Blue Lan、Karine Auclair

  DOI：10.1002/ejoc.202400071

  日期：2024.3.25

  The readily available organocatalyst 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD) was used for the rapid synthesis of 3‐hydroxyisoindolin‐1‐ones from 3‐alkylidenephthalides. The transformation occurs at room temperature and requires less solvent than traditional methods, providing a more sustainable synthetic option to access 3‐hydroxyisoindolin‐1‐ones with broad scope. Elaboration of the products to diverse scaffolds as well as synthesis of biologically active compounds are demonstrated.

  摘要 利用容易获得的有机催化剂 1,5,7-三氮杂双环[4.4.0]癸-5-烯（TBD），从 3-亚烷基酞化物快速合成 3-羟基异吲哚啉-1-酮。与传统方法相比，该转化过程在室温下进行，所需的溶剂更少，为获得范围广泛的 3-羟基异吲哚啉-1-酮提供了更可持续的合成选择。该研究展示了如何将产品加工成不同的支架以及合成具有生物活性的化合物。
• Assembly of Substituted 3-Methyleneisoindolin-1-ones via a CuI/<scp>l</scp>-Proline-Catalyzed Domino Reaction Process of 2-Bromobenzamides and Terminal Alkynes
  作者：Li Li、Miao Wang、Xiaojing Zhang、Yongwen Jiang、Dawei Ma

  DOI：10.1021/ol9000922

  日期：2009.3.19

  CuI/L-proline catalyzed coupling of 2-bromobenzamides and terminal alkynes in PrOH (or DMF and DMSO) at 85-110 degrees C and subsequent additive cyclization produces substituted 3-methyleneisoindolin-1-ones. Variation of N-substituents, aromatic ring, and methylene part is possible by using suitable starting materials.
• 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.