1,2,3,5,6,7-Hexahydro-4a-aza-3a-azonia-cyclopenta[def]phenanthrene; chloride | 786688-16-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯嗪
• 英文名称: 1,2,3,5,6,7-Hexahydro-4a-aza-3a-azonia-cyclopenta[def]phenanthrene; chloride
• CAS: 786688-16-2
• 化学式: C₁₃H₁₅N₂*Cl
• 分子量: 234.728
• InChiKey: ZADHWRWKJSSGTM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.17
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  8.81
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  silver(l) oxide 、 1,2,3,5,6,7-Hexahydro-4a-aza-3a-azonia-cyclopenta[def]phenanthrene; chloride 以 二氯甲烷 为溶剂， 以75%的产率得到bis(1,2,3,5,6,7-hexahydro-3a,4a-diazacyclopenta[def]phenanthren-4-ylidene)silver(I)-AgCl2
  参考文献：
  名称：

  Neutral and Cationic Iridium(I) Complexes Bearing Chiral Phenanthroline-Derived Benzimidazolylidenes: Synthetic, Structural, and Catalytic Studies

  摘要：

  A series of neutral and cationic iridium(I) complexes bearing chiral and achiral phenanthroline-derived benzimidazolylidene ligands were synthesized and characterized. Spectroscopic and crystallographic data indicate that the principal plane of the NHC ligand in the achiral complexes is positioned orthogonally with respect to the Ir-Cl or Ir-P bonds, while the planes of NHC ligands in the corresponding chiral complexes are twisted by a torsion angle that depends on the size of the 2,9-substituents. All of the new complexes showed varying degrees of catalytic activity and enantioselectivity toward hydrogenation of acetamidoacrylates, with the best results being achieved using 2,9-diphenyl-substituted (S,S)-20a, which afforded (-)-(R)-methyl 2-acetamidopropanoate (12a) in 97% yield and 81 % ee.

  DOI：

  10.1021/om801063w
• 作为产物：
  描述：

  1,10-菲罗啉 在 盐酸 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 24.5h， 生成 1,2,3,5,6,7-Hexahydro-4a-aza-3a-azonia-cyclopenta[def]phenanthrene; chloride
  参考文献：
  名称：

  A Benzimidazole-Based N-Heterocyclic Carbene Derived from 1,10-Phenanthroline

  摘要：

  A catalytically active palladium-complexed tetracyclic N-heterocyclic carbene (NHC) was prepared in three steps from commercially available 1,10-phenanthroline by using a reduction-cyclization-deprotonation sequence. The new carbene framework is a prototype for the development of a series of chiral N-heterocyclic carbenes.

  DOI：

  10.1021/ol048393k