N-(2,5-di-tert-butylphenyl) maleimide | 128869-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: N-(2,5-di-tert-butylphenyl) maleimide
• 英文别名: 1-(2,5-Ditert-butylphenyl)pyrrole-2,5-dione；1-(2,5-ditert-butylphenyl)pyrrole-2,5-dione
• CAS: 128869-06-7
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: OBBPAIHCLLXNEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2,5-di-tert-butylphenyl) maleimide 、 四溴甲苯 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以21%的产率得到N,N'-bis(2,5-di-tert-butylphenyl)-1,2,3,4,5,6,7,8-octahydro-2,3,6,7-anthracenetetracarboxylic 2,3:6,7-diimide
  参考文献：
  名称：

  Electrochemistry and near-infrared spectra of anion radicals containing several imide or quinone groups

  摘要：

  DOI：

  10.1021/jo00303a008
• 作为产物：
  描述：

  2,5-二叔丁基硝基苯 在 盐酸 、 铁粉 作用下， 以 乙醇 为溶剂， 反应 49.0h， 生成 N-(2,5-di-tert-butylphenyl) maleimide
  参考文献：
  名称：

  Rotational features of carbon-nitrogen bonds in N-aryl maleimides. Atroposelective reactions of o-tert-butylphenylmaleimides

  摘要：

  Atroposelective addition and cycloaddition reactions of N-2-(tert-butylphenyl)- and N-2,5-(di-tert-butylphenyl)maleimide and a substituted derivative have been studied. Good to excellent stereoselectivities are generally observed, and high rotation barriers (about 29 kcal/mol) prevent the products from interconverting. Crystal structures of the precursors and products support a straight forward model where reactants attack trans to the o-tert-butyl group. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00237-9

文献信息

• Michael Addition of Oxindoles to N-(2-tert-Butylphenyl)maleimides: Efficient Desymmetrization for the Synthesis of Atropisomeric Succinimides with Quaternary and Tertiary Stereocenters
  作者：Giorgio Bencivenni、Nicola Di Iorio、Lorenzo Soprani、Simone Crotti、Emanuela Marotta、Andrea Mazzanti、Paolo Righi

  DOI：10.1055/s-0036-1588408

  日期：——

  Abstract The desymmetrization of N-(2-tert-butylphenyl)maleimides was realized by means of a Michael reaction of N-(tert-butoxycarbonyl)-3-phenyloxindoles leading to the corresponding axially chiral succinimides in high yields. The use of a squaramide cinchonidine organocatalyst was fundamental to achieve the simultaneous remote control of the stereogenic axis and adjacent quaternary and tertiary stereocenters

  摘要 N-（2-叔丁基苯基）马来酰亚胺的脱对称化是通过N-（叔丁氧基羰基）-3-苯基氧吲哚的迈克尔反应以高产率产生相应的轴向手性琥珀酰亚胺而实现的。使用方酰胺辛可尼定有机催化剂是实现立体轴和相邻的四级和三级立体中心同时远程控制的基础。 N-（2-叔丁基苯基）马来酰亚胺的脱对称化是通过N-（叔丁氧基羰基）-3-苯基氧吲哚的迈克尔反应以高产率产生相应的轴向手性琥珀酰亚胺而实现的。使用方酰胺辛可尼定有机催化剂是实现立体轴和相邻的四级和三级立体中心同时远程控制的基础。
• Atroposelective Thermal Reactions of Axially Twisted Amides and Imides
  作者：Dennis P. Curran、Hongyan Qi、Steven J. Geib、Nicholas C. DeMello

  DOI：10.1021/ja00086a056

  日期：1994.4
• Targeting remote axial chirality control of N-(2-tert-butylphenyl)succinimides by means of Michael addition type reactions
  作者：Nicola Di Iorio、Florian Champavert、Agostino Erice、Paolo Righi、Andrea Mazzanti、Giorgio Bencivenni

  DOI：10.1016/j.tet.2016.02.052

  日期：2016.8

  The efficient desymmetrization of N-(2-tert-butylphenyl)maleimides was realized by means of a Michael addition reaction of a series of carbon nucleophiles generating the corresponding axially chiral succinimides in high yields. The use of (DHQD)(2)Pyr as catalyst was fundamental to achieve the remote control of the stereogenic chiral axis with the concurrent construction of adjacent quaternary and tertiary stereocenters. (C) 2016 Elsevier Ltd. All rights reserved.
• Organocatalytic Atroposelective Formal Diels–Alder Desymmetrization of <i>N</i>-Arylmaleimides
  作者：Florine Eudier、Paolo Righi、Andrea Mazzanti、Alessia Ciogli、Giorgio Bencivenni

  DOI：10.1021/acs.orglett.5b00509

  日期：2015.4.3

  The atroposelective desymmetrization of N-arylmaleimides was realized by means of a primary amine catalyzed Diels-Alder reaction of enones. The chiral axis as new element of chirality is generated under the remote control of the catalyst that selectively drives the formal Diels-Alder reaction through an exclusive stereochemical outcome.
• Electrochemistry and near-infrared spectra of anion radicals containing several imide or quinone groups
  作者：Stanton F. Rak、Thomas H. Jozefiak、Larry L. Miller

  DOI：10.1021/jo00303a008

  日期：1990.8