benzyl (4-(tert-butyl)-3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl)carbamate | 1620078-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: benzyl (4-(tert-butyl)-3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl)carbamate
• CAS: 1620078-28-5
• 化学式: C₂₂H₂₂N₂O₄
• 分子量: 378.428
• InChiKey: DTZANOSWDUAPTK-UHFFFAOYSA-N

物化性质

• 沸点：
  506.7±50.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  75.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-丙-2-基环己-2-烯-1-酮 、 benzyl (4-(tert-butyl)-3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl)carbamate 在 (9R)-6'-甲氧基奎宁-9-胺三盐酸盐 、 奎宁胺 作用下， 以 甲苯 为溶剂， 反应 72.08h， 生成 (Ra)-(3S)-benzyl (4-(tert-butyl)-3-(2,5-dioxo-3-(2-(3-oxocyclohex-1-en-1-yl)propan-2-yl)pyrrolidin-1-yl)phenyl)carbamate
  参考文献：
  名称：

  轴向手性的远程控制：N-芳基马来酰亚胺通过乙烯基迈克尔加成的氨基催化去对称化

  摘要：

  N-(2-t-丁基苯基)琥珀酰亚胺的轴向手性的远程控制是通过3-取代的环己烯酮与N-(2-t-丁基苯基)马来酰亚胺的乙烯基迈克尔加成实现的。9-氨基（9-脱氧）表奎宁促进对映选择性去对称化，导致具有两个相邻立体中心的阻转异构琥珀酰亚胺。

  DOI：

  10.1021/ja505610k

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。
• 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.