(4S,7R)-7,8,8-trimethyl-4,5,6,7-tetrahydro-4,7-methano-1-phenylindazol-3-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (4S,7R)-7,8,8-trimethyl-4,5,6,7-tetrahydro-4,7-methano-1-phenylindazol-3-carboxylic acid
• 英文别名: (1R,7S)-1,10,10-trimethyl-3-phenyl-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxylic acid
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: TWKWHPUPCOCRHI-XIKOKIGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,7R)-7,8,8-trimethyl-4,5,6,7-tetrahydro-4,7-methano-1-phenylindazol-3-carboxylic acid 在 氯化亚砜 作用下， 反应 3.0h， 以85%的产率得到(4S,7R)-7,8,8-trimethyl-4,5,6,7-tetrahydro-4,7-methano-1-phenylindazol-3-carbonyl chloride
  参考文献：
  名称：

  Camphopyrazole-based N,N- and N,P-ligands and chiral complexes of Ni, Pd, and Rh: P–N bond activation upon Rh(I) complexation

  摘要：

  Enantiomerically pure C-1 and C-2-symmetric bidentate N,N- and N,P-ligands are accessible from (+)-camphor in good yields (60-90%). Modified syntheses of precursors 1 and 2 are disclosed as well as the crystal structures of three hydroxy-pyrazoline intermediates. Ligands 3, 4, 6, and 11 were fully characterized including an X-ray crystal structure of C-2-symmetric 6, which showed an E-configuration in the solid state. These ligands form complexes with Ni(II), Pd(II), and Rh(I) in good yields (84-96%); the X-ray crystal structures of complexes 12, 14, and 16 confirmed the bidentate coordination modes of ligands 4, 6, and 11 and distorted tetrahedral [for NON and square planar [for Rh(I)] coordination geometries. Furthermore, the structure of the Rh(I) complex 16 revealed the presence of a Ph2PCl ligand, which, along with spectroscopic data, is proof of an almost quantitative P-N bond cleavage upon coordination of ligand 11 to [RhCl(COD)](2). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.06.013
• 作为产物：
  描述：

  白樟油 在 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.25h， 生成 (4S,7R)-7,8,8-trimethyl-4,5,6,7-tetrahydro-4,7-methano-1-phenylindazol-3-carboxylic acid
  参考文献：
  名称：

  Camphopyrazole-based N,N- and N,P-ligands and chiral complexes of Ni, Pd, and Rh: P–N bond activation upon Rh(I) complexation

  摘要：

  Enantiomerically pure C-1 and C-2-symmetric bidentate N,N- and N,P-ligands are accessible from (+)-camphor in good yields (60-90%). Modified syntheses of precursors 1 and 2 are disclosed as well as the crystal structures of three hydroxy-pyrazoline intermediates. Ligands 3, 4, 6, and 11 were fully characterized including an X-ray crystal structure of C-2-symmetric 6, which showed an E-configuration in the solid state. These ligands form complexes with Ni(II), Pd(II), and Rh(I) in good yields (84-96%); the X-ray crystal structures of complexes 12, 14, and 16 confirmed the bidentate coordination modes of ligands 4, 6, and 11 and distorted tetrahedral [for NON and square planar [for Rh(I)] coordination geometries. Furthermore, the structure of the Rh(I) complex 16 revealed the presence of a Ph2PCl ligand, which, along with spectroscopic data, is proof of an almost quantitative P-N bond cleavage upon coordination of ligand 11 to [RhCl(COD)](2). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.06.013