3-methyl-2,3,4,10-tetrahydro-1H-acridin-9-one | 72136-22-2

• 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: 3-methyl-2,3,4,10-tetrahydro-1H-acridin-9-one
• CAS: 72136-22-2
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: LBZJMXMOGKQFJV-UHFFFAOYSA-N

物化性质

• 熔点：
  361.5-366.2 °C
• 沸点：
  353.7±42.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-2,3,4,10-tetrahydro-1H-acridin-9-one 在 三氯氧磷 作用下， 生成 3-methyl-10H-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
• 作为产物：
  描述：

  3-甲基环己酮 生成 3-methyl-2,3,4,10-tetrahydro-1H-acridin-9-one
  参考文献：
  名称：

  Perkin; Sedgwick, Journal of the Chemical Society, 1924, vol. 125, p. 2449

  摘要：

  DOI：

文献信息

• Desai; Shintre, Journal of the Indian Chemical Society, 1956, vol. 33, p. 425,428
  作者：Desai、Shintre

  DOI：——

  日期：——
• 115. Hydroacridones. Synthesis and dehydrogenation
  作者：R. A. Reed

  DOI：10.1039/jr9440000425

  日期：——
• OSBIRK A.; PEDERSEN E. B., ACTA CHEM. SCAND., 1979, B 33, NO 5, 313-318
  作者：OSBIRK A.、 PEDERSEN E. B.

  DOI：——

  日期：——
• Tetrahydroacridin-9-ones, 9-chlorotetrahydroacridines, 9-amino-tetrahydroacridines and 9-(pyrazol-1-yl)-tetrahydroacridines derived from chiral cyclanones
  作者：Aline Frideling、Robert Faure、Jean-Pierre Galy、Ahmed Kenz、Ibon Alkorta、José Elguero

  DOI：10.1016/j.ejmech.2003.10.003

  日期：2004.1

  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.
• Perkin; Sedgwick, Journal of the Chemical Society, 1924, vol. 125, p. 2449
  作者：Perkin、Sedgwick

  DOI：——

  日期：——