7,8-二苯基-[1,3]二氧杂环戊并[4,5-g]异喹啉 | 385416-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 7,8-二苯基-[1,3]二氧杂环戊并[4,5-g]异喹啉
• 英文名称: 7,8-diphenyl-1,3-dioxolo[4,5-g]isoquinoline
• 英文别名: 7,8-Diphenyl-[1,3]dioxolo[4,5-G]isoquinoline
• CAS: 385416-36-4
• 化学式: C₂₂H₁₅NO₂
• 分子量: 325.367
• InChiKey: GMODXMZZVJOKNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-iodopiperonal 在 1,2-双(二苯基膦)乙烷氯化镍 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 生成 7,8-二苯基-[1,3]二氧杂环戊并[4,5-g]异喹啉
  参考文献：
  名称：

  镍催化炔烃的亚氨基环化反应在室温下高区域选择性异喹啉的合成

  摘要：

  空气稳定且价格便宜的Ni（dppe）Cl 2以及Et 3 N在室温下可有效催化炔烃的亚氨基环化反应，从而可以高收率和完全的区域选择性制备重要的3,4-二取代和3-取代的异喹啉。这些成环反应的特点是基材范围广，可扩展性强，操作简便且实用性强。

  DOI：

  10.1002/ejoc.201800341

文献信息

• Highly Efficient Synthesis of Isoquinolines via Nickel-Catalyzed Annulation of 2-Iodobenzaldimines with Alkynes:  Evidence for Dual Pathways of Alkyne Insertion
  作者：Rajendra Prasad Korivi、Chien-Hong Cheng

  DOI：10.1021/ol0519994

  日期：2005.11.1

  [reaction: see text] A wide range of substituted isoquinolines were synthesized via a highly efficient nickel-catalyzed annulation of the tert-butyl imines of 2-iodobenzaldehydes and various alkynes; examination of the regiochemistry of isoquinolines synthesized indicates that there are two different alkyne insertion pathways for the catalytic reactions.

  [反应：见正文]通过高效的镍催化的2-碘联苯甲醛和各种炔烃的叔丁基亚胺合成了各种各样的取代异喹啉。对合成的异喹啉区域化学的检查表明，有两种不同的炔烃插入途径可用于催化反应。
• Facile synthesis of isoquinolines by imination and subsequent palladacycle-catalyzed iminoannulation of internal alkynes
  作者：Fan Yang、Junli Zhang、Yangjie Wu

  DOI：10.1016/j.tet.2011.02.044

  日期：2011.4

  An efficient and facile synthesis of isoquinolines has been described via a tandem reaction of imination of o-halobenzaldehydes with tert-butyl amine and subsequent palladacycle-catalyzed iminoannulation of internal alkynes. This tandem reaction could be carried out successively in one pot without any special operation, and the annulation step could afford isoquinolines derivatives in moderate to good

  已经描述了通过邻卤代苯甲醛与叔丁胺的串联反应和随后的palladacycle催化的内部炔基亚氨基环化反应的异喹啉的高效简便合成方法。该串联反应可以在一个锅中连续进行而无需任何特殊操作，并且该环合步骤可以以中等至良好的产率提供具有高区域选择性的异喹啉衍生物。此外，吲哚的简单合成是通过palladacycle催化的o-碘苯胺或o-溴苯胺与内部炔烃的环合反应实现的。
• Synthesis of Isoquinolines and Pyridines by the Palladium-Catalyzed Iminoannulation of Internal Alkynes
  作者：Kevin R. Roesch、Haiming Zhang、Richard C. Larock

  DOI：10.1021/jo0105540

  日期：2001.11.1

  A wide variety of substituted isoquinoline, tetrahydroisoquinoline, 5,6-dihydrobenz[f]isoquinoline, pyrindine, and pyridine heterocycles have been prepared in good to excellent yields via annulation of internal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst. The best results are obtained by employing 5 mol % of Pd(OAc)(2), an excess of the alkyne, 1 equiv of Na2CO3 as a base, and 10 mol % of PPh3 in DMF as the solvent. This annulation methodology is particularly effective for aryl- or alkenyl-substituted alkynes. When electron-rich imines are employed, this chemistry can be extended to alkyl-substituted alkynes. Trimethylsilyl-substituted alkynes also undergo this annulation process to afford monosubstituted heterocyclic products absent the silyl group.
• Highly Regioselective Isoquinoline Synthesis via Nickel-Catalyzed Iminoannulation of Alkynes at Room Temperature
  作者：Jian-Guo Sun、Xiao-Yu Zhang、Hua Yang、Ping Li、Bo Zhang

  DOI：10.1002/ejoc.201800341

  日期：2018.9.23

  The air‐stable and inexpensive Ni(dppe)Cl2 along with Et3N efficiently catalyzes the iminoannulation of alkynes at room temperature, allowing for the preparation of important 3,4‐disubstituted and 3‐substituted isoquinolines in high yields with complete regioselectivity. These annulation reactions feature a broad substrate scope, easy scalability, operational simplicity, and excellent practicality

  空气稳定且价格便宜的Ni（dppe）Cl 2以及Et 3 N在室温下可有效催化炔烃的亚氨基环化反应，从而可以高收率和完全的区域选择性制备重要的3,4-二取代和3-取代的异喹啉。这些成环反应的特点是基材范围广，可扩展性强，操作简便且实用性强。