(R)-3-Methyl-1,3,4,10-tetrahydro-2H-acridin-9-one | 691359-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (R)-3-Methyl-1,3,4,10-tetrahydro-2H-acridin-9-one
• CAS: 691359-74-7
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: LBZJMXMOGKQFJV-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  32.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R)-3-Methyl-1,3,4,10-tetrahydro-2H-acridin-9-one 在 三氯氧磷 作用下， 以72%的产率得到(R)-9-chloro-3-methyl-1,2,3,4-tetrahydroacridine
  参考文献：
  名称：

  Tetrahydroacridin-9-ones, 9-chlorotetrahydroacridines, 9-amino-tetrahydroacridines and 9-(pyrazol-1-yl)-tetrahydroacridines derived from chiral cyclanones

  摘要：

  A series of tetrahydroacridines related to tacrine have been synthesized starting from 3-methylcyclohexananone, menthone, pulegone, carvone and dihydrocarvone (both racemic and chiral). In many cases, the yields and purity of the compounds have been improved by the use of a microwave oven. These compounds have been characterized by H-1 and C-13 NMR data. To establish their relative configuration, the structure of (1R,4R)-(+)-9-chloro-1-methyl-4-isopropyl-1,2,3,4-tetrahydroacridine (cis-10b), derived from (2S,5R)-(-)-menthone, has been determined by X-ray. The chemical shifts of cis-10b and trans-10b have been calculated at the GIAO/B3LYP/6-31G* level and compared successfully with the experimental data. (C) 2003 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.10.003
• 作为产物：
  描述：

  (R)-(+)-3-甲基环己酮 、 邻氨基苯甲酸 反应 0.05h， 以69%的产率得到(R)-3-Methyl-1,3,4,10-tetrahydro-2H-acridin-9-one
  参考文献：
  名称：

  Tetrahydroacridin-9-ones, 9-chlorotetrahydroacridines, 9-amino-tetrahydroacridines and 9-(pyrazol-1-yl)-tetrahydroacridines derived from chiral cyclanones

  摘要：

  A series of tetrahydroacridines related to tacrine have been synthesized starting from 3-methylcyclohexananone, menthone, pulegone, carvone and dihydrocarvone (both racemic and chiral). In many cases, the yields and purity of the compounds have been improved by the use of a microwave oven. These compounds have been characterized by H-1 and C-13 NMR data. To establish their relative configuration, the structure of (1R,4R)-(+)-9-chloro-1-methyl-4-isopropyl-1,2,3,4-tetrahydroacridine (cis-10b), derived from (2S,5R)-(-)-menthone, has been determined by X-ray. The chemical shifts of cis-10b and trans-10b have been calculated at the GIAO/B3LYP/6-31G* level and compared successfully with the experimental data. (C) 2003 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.10.003