2-phenyl-5'-nitrobenzo[d]benzo[h]-6-aza-1,3-dioxa-2-boracyclonon-6-ene | 862095-14-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-phenyl-5'-nitrobenzo[d]benzo[h]-6-aza-1,3-dioxa-2-boracyclonon-6-ene
• 英文别名: 14-Nitro-1-phenyl-2,17-dioxa-10-azonia-1-boranuidatetracyclo[8.7.0.03,8.011,16]heptadeca-3,5,7,9,11(16),12,14-heptaene
• CAS: 862095-14-5
• 化学式: C₁₉H₁₃BN₂O₄
• 分子量: 344.134
• InChiKey: XIVLDOFSCOHGPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-phenyl-5'-nitrobenzo[d]benzo[h]-6-aza-1,3-dioxa-2-boracyclonon-6-ene 在 potassium cyanide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以94%的产率得到2-(o-Hydroxyphenyl)-6-nitrobenzoxazol
  参考文献：
  名称：

  An efficient potassium cyanide-promoted synthesis of 2-arylbenzoxazoles from [4.3.0]boron heterobicycles

  摘要：

  The 2-arylbenzoxazoles 3a-f were produced in moderate to excellent yields merely by stirring a potassium cyanide (3 equiv)-containing methanol solution of the borobicyclic compounds 1a-f at room temperature. These compounds were fully characterized spectroscopically [1R, H-1, and C-13 NMR and X-ray analysis (3a)] and by elemental analysis. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.027
• 作为产物：
  描述：

  2-[[(2-hydroxy-4-nitrophenyl)imino]methyl] phenol 、 苯硼酸 以 四氢呋喃 为溶剂， 以92%的产率得到2-phenyl-5'-nitrobenzo[d]benzo[h]-6-aza-1,3-dioxa-2-boracyclonon-6-ene
  参考文献：
  名称：

  亚氨基狄尔斯-硼酸酯的der醛反应：3,4-二氢喹啉的新途径

  摘要：

  描述了通过Imino Diels-Alder反应合成的一系列3,4-二氢喹啉（3b – e，3h和3i），其中涉及亚砜和席夫碱衍生的硼酸酯2a – j。该反应是区域选择性的，导致4-取代的二氢喹啉，其在硼原子上的苯基与4位上的乙烯基取代基之间具有顺式相对立体化学，如通过3b，3e，3h和3i的X射线衍射分析所建立的。

  DOI：

  10.1016/j.jorganchem.2005.03.024

文献信息

• Imino Diels–Alder reaction of boronates. Preparation and characterization of new 3,4-dihydroquinoline and 1,2,3,6-tetrahydropyridine derivatives
  作者：Mario Rodríguez、Ma. Eugenia Ochoa、Cristina Rodríguez、Rosa Santillan、Víctor Barba、Norberto Farfán

  DOI：10.1016/j.jorganchem.2007.02.012

  日期：2007.5

  The preparation of 3,4-dihydroquinolines (2a-d and 3a,b,d), as well as 1,2,3,6-tetrahydropyridines (4a-e) by imino Diels-Alder reaction of boronates (1a-e) with 2,3-dimethylbutadiene is reported. Boronates (1a-d) containing substituents meta and para relative to the imino fragment lead to diastereomeric mixtures of 4-methyl-4-ethenyt-3,4-dihydroquinolines (2, 3) and tetrahydropyridines (4). In contrast, the presence of an electron withdrawing substituent at the para position (1e), favors the iminodienophile behavior giving 4,5-dimethyl-1,2,3,6-tetrahydropyridine (4e) as the main product. The results show that boronates derived from Schiff bases are electron deficient species which can act either as dienophiles or dienes in the reaction with 2,3-dimethylbutadiene to give 3,4-dihydroquinolines and 1,2,3,6-tetrahydropyridines. All products were characterized by NMR and X-ray diffraction analysis of 2b, 2d, 3d and 4c allowed to assign the relative configuration of the newly formed stereogenic centers. (c) 2007 Elsevier B.V. All rights reserved.