N-phenyltricyclo[2.2.1]heptane-2β,6β-dicarboximide | 29910-09-6

• 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: N-phenyltricyclo[2.2.1]heptane-2β,6β-dicarboximide
• 英文别名: 2-phenyl-(3ac,7ac)-hexahydro-4r,7c-methano-isoindole-1,3-dione；2-Phenyl-(3ac,7ac)-hexahydro-4r,7c-methano-isoindol-1,3-dion；(1S,2S,6R,7R)-4-phenyl-4-azatricyclo[5.2.1.02,6]decane-3,5-dione
• CAS: 29910-09-6
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: APOBYZSYMJNZIE-NIFPGPBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 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-phenyltricyclo[2.2.1]heptane-2β,6β-dicarboximide 在 trans-[Ru((R)-BINAP)(H)2((R,R)-dpen)] 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以44%的产率得到(1R,2R,6S,7S)-5-Hydroxy-4-phenyl-4-aza-tricyclo[5.2.1.0^2,6]decan-3-one
  参考文献：
  名称：

  通过对映选择性单氢化反应去对称化中环酰亚胺

  摘要：

  使用反式-[Ru((R)-BINAP)(H)(2)((R,R)-dpen)] 和相关化合物，将内消旋酰亚胺单氢化以形成 88-97% ee 的相应羟基内酰胺THF 中碱的催化剂。氢化以高对映基团和化学选择性进行，它是一种去对称化反应，在一个反应​​中形成多达五个立体中心。羟基内酰胺转化为相应的亚胺离子，然后加入茚将立体中心的数量从 5 扩展到 7。

  DOI：

  10.1021/ja105783u
• 作为产物：
  描述：

  3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 1,4-二氧六环 、 氯仿 、 镍 作用下， 生成 N-phenyltricyclo[2.2.1]heptane-2β,6β-dicarboximide
  参考文献：
  名称：

  Null Mutation in Puroindoline A is Prevalent in Indian Wheats: Puroindoline Genes are Located in The Distal Part of 5DS

  摘要：

  PCR amplification and protein analysis of pinA and pinB, the two components of friabilin, a marker protein for grain softness, were carried out in one hundred varieties from India and forty varieties from Kansas State, USA. Glycine to serine change in pinB or null mutation in pinA (absence of gene) has been reported linked with grain hardness. Here we report that majority of Kansas State hard wheats possess glycine to serine mutation in pinB and few have null mutation in pinA. In contrast, majority of varieties released in India are hard and have null mutation in pinA. There are some exceptions where some hard wheats in India do not exhibit either null mutation in pinA or glycine to serine change in pinB. There might be some additional mutations that are to be characterised in elucidating the molecular basis of hardness for usage in genetic engineering. PinA and pinB genes have been assigned on the distal part of 5D short arm using deletion lines of chinese spring wheat where hardness gene Ha is reported to be present.

  DOI：

  10.1007/bf03263140

文献信息

• [EN] PROCESS FOR THE ASYMMETRIC HYDROGENATION OF IMIDES<br/>[FR] PROCÉDÉ POUR L'HYDROGÉNATION ASYMÉTRIQUE D'IMIDES
  申请人：UNIV ALBERTA

  公开号：WO2010145024A1

  公开（公告）日：2010-12-23

  The present disclosure provides a process for the mono-reduction of one or more imide moieties in a compound comprising contacting the compound with hydrogen gas and a catalyst comprising a transition metal hydride in the presence of a base, under conditions for the mono-reduction of the one or more imide moieties to form a compound comprising one or more hydroxy amides.

  本公开提供了一种单一还原一个或多个酰亚胺基团的化合物的过程，包括将该化合物与氢气和催化剂接触，所述催化剂包括过渡金属氢化物，在碱的存在下，在单一还原一个或多个酰亚胺基团的条件下形成一个含有一个或多个羟基酰胺的化合物。
• Double Methylenecyclopentane Annulation of Succinimides: Easy Access to 3,7-Dioxobicyclo[3.3.0]octane-1,5-dicarboximides
  作者：Pelayo Camps、José A. Fernández、Jordi Rull、Santiago Vázquez

  DOI：10.1002/ejoc.200900273

  日期：2009.6

  N-Alkylsuccinimides reacted with excess of LHMDS and 3-chloro-2-(chloromethyl)-1-propene to give in medium yieldsN-alkyl-3,7-dimethylenebicyclo[3.3.0]octane-1,5-dicarboximides, which were ozonized to the corresponding 3,7-dioxobicyclo[3.3.0]octane-1,5-dicarboximides. When these alkylations were carried out by using LDA as the base, cis-N-alkyl-4-methylenecyclopentane-1,2-dicarboximides were mainly obtained

  N-烷基琥珀酰亚胺与过量的 LHMDS 和 3-氯-2-(氯甲基)-1-丙烯反应，得到中等产率的 N-烷基-3,7-二亚甲基双环[3.3.0]辛烷-1,5-二甲酰亚胺，它们是臭氧化为相应的 3,7-二氧双环 [3.3.0] 辛烷-1,5-二甲酰亚胺。当使用 LDA 作为碱进行这些烷基化时，尽管使用了过量的碱和烷基化剂，但主要获得了顺式-N-烷基-4-亚甲基环戊烷-1,2-二甲酰亚胺。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Asymmetric catalytic reduction of meso-imides
  作者：Jahyo Kang、Jun Won Lee、Joo In Kim、Chongsuh Pyun

  DOI：10.1016/0040-4039(95)00728-u

  日期：1995.6

  A thiazazincolidine complex, 1, was shown to be an excellent catalyst for enantioselective reduction with bis(2,6-dimethylphenoxy)borane (BDMPB) of meso N-phenylimides in high ee to the corresponding hydroxy lactams, which were eventually converted to the corresponding lactones of high optical purity.
• GARRATT, P. J.;HOLLOWOOD, F., J. ORG. CHEM., 1982, 47, N 1, 68-72
  作者：GARRATT, P. J.、HOLLOWOOD, F.

  DOI：——

  日期：——
• PROCESS FOR THE ASYMMETRIC HYDROGENATION OF IMIDES
  申请人：Bergens Steven H.

  公开号：US20120165546A1

  公开（公告）日：2012-06-28

  The present disclosure provides a process for the mono-reduction of one or more imide moieties in a compound comprising contacting the compound with hydrogen gas and a catalyst comprising a transition metal hydride in the presence of a base, under conditions for the mono-reduction of the one or more imide moieties to form a compound comprising one or more hydroxy amides.