Benzamide, N,N'-(4,5-dichloro-3,5-cyclohexadiene-1,2-diylidene)bis- | 820246-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzamide, N,N'-(4,5-dichloro-3,5-cyclohexadiene-1,2-diylidene)bis-
• 英文别名: N-(6-benzoylimino-3,4-dichlorocyclohexa-2,4-dien-1-ylidene)benzamide
• CAS: 820246-27-3
• 化学式: C₂₀H₁₂Cl₂N₂O₂
• 分子量: 383.233
• InChiKey: SMJHJWDMRYXEDY-UHFFFAOYSA-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Benzamide, N,N'-(4,5-dichloro-3,5-cyclohexadiene-1,2-diylidene)bis- 、 2-chloro-3-phenyl-propionaldehyde 在 (5aR,10bS)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride 、 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以49%的产率得到(R)-1,4-dibenzoyl-3-benzyl-6,7-dichloro-3,4-dihydroquinoxalin-2(1H)-one
  参考文献：
  名称：

  Carbene-Catalyzed α-Carbon Amination of Chloroaldehydes for Enantioselective Access to Dihydroquinoxaline Derivatives

  摘要：

  An NHC-catalyzed alpha-carbon amination of chloroaldehydes was developed. Cyclohexadiene-1,2-diimines are used as amination reagents and four-atom synthons. Our reaction affords optically enriched dihydroquinoxalines that are core structures in natural products and synthetic bioactive molecules.

  DOI：

  10.1021/acs.orglett.9b01520
• 作为产物：
  描述：

  N,N'-(4,5-dichloro-o-phenylene)-bis-benzamide 在 lead(IV) tetraacetate 作用下， 以 氯仿 为溶剂， 生成 Benzamide, N,N'-(4,5-dichloro-3,5-cyclohexadiene-1,2-diylidene)bis-
  参考文献：
  名称：

  Carbene-Catalyzed α-Carbon Amination of Chloroaldehydes for Enantioselective Access to Dihydroquinoxaline Derivatives

  摘要：

  An NHC-catalyzed alpha-carbon amination of chloroaldehydes was developed. Cyclohexadiene-1,2-diimines are used as amination reagents and four-atom synthons. Our reaction affords optically enriched dihydroquinoxalines that are core structures in natural products and synthetic bioactive molecules.

  DOI：

  10.1021/acs.orglett.9b01520

文献信息

• Lewis Acid Catalyzed Addition of Allylsilane to<i>o</i>-Quinonediimides: Formal Diels-Alder Reaction versus Allylation
  作者：Vijay Nair、R. Dhanya、N. Vidya、S. Devipriya

  DOI：10.1055/s-2005-918494

  日期：——

  Lewis acid promoted addition of allylsilane to o-quinonediimines afforded tetrahydroquinoxaline derivatives or allylated amides, depending on the nature of the substituent on the imine nitrogen.

  根据亚胺氮上取代基的性质，路易斯酸促进烯丙基硅烷与邻醌二亚胺的加成得到四氢喹喔啉衍生物或烯丙基化酰胺。
• Lewis Acid-Promoted Annulation of <i>o</i>-Quinonediimines by Allylstannane:  A Facile Synthesis of Quinoxaline Derivatives
  作者：Vijay Nair、R. Dhanya、C. Rajesh、Mohan M. Bhadbhade、K. Manoj

  DOI：10.1021/ol048004m

  日期：2004.12.1

  Lewis acid-promoted addition of allyltri-n-butylstannane to o-quinonediimines afforded tetrahydroquinoxaline derivatives or allylated amides depending on the nature of the substituent on imine nitrogen.
• Carbene-Catalyzed α-Carbon Amination of Chloroaldehydes for Enantioselective Access to Dihydroquinoxaline Derivatives
  作者：Ruoyan Huang、Xingkuan Chen、Chengli Mou、Guoyong Luo、Yongjia Li、Xiangyang Li、Wei Xue、Zhichao Jin、Yonggui Robin Chi

  DOI：10.1021/acs.orglett.9b01520

  日期：2019.6.7

  An NHC-catalyzed alpha-carbon amination of chloroaldehydes was developed. Cyclohexadiene-1,2-diimines are used as amination reagents and four-atom synthons. Our reaction affords optically enriched dihydroquinoxalines that are core structures in natural products and synthetic bioactive molecules.