5,5-dimethyl-3,4,5,6-tetrahydro-3-benz[c]phenanthridinone | 146306-25-4

• 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: 5,5-dimethyl-3,4,5,6-tetrahydro-3-benz[c]phenanthridinone
• 英文别名: 9,9-dimethyl-7,8,9,10-tetrahydrobenzphenanthridin-7-one；9,9-dimethyl-7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-one；9,9-dimethyl-8,10-dihydrobenzo[c]phenanthridin-7-one
• CAS: 146306-25-4
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: ZNMRZYXUWFCOEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-3,4,5,6-tetrahydro-3-benz[c]phenanthridinone 在 sodium tetrahydroborate 作用下， 以 水 、 异丙醇 为溶剂， 反应 23.0h， 以73%的产率得到9,9-dimethyl-7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-oi
  参考文献：
  名称：

  Synthesis of new benzo[c]phenanthridine derivatives

  摘要：

  Three-component condensation of naphthalen-1-amine with triethyl orthoformate and dimedone or cyclopentane-1,3-dione, as well as the reaction of naphthalen-1-amine with 2-acetyl-5,5-dimethylcyclohexane-1,3-dione, gave the corresponding 2-[1-(alpha-naphthylamino)alkylidene]cycloalkane-1,3-diones which underwent intramolecular cyclization to 7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-one derivatives on heating in polyphosphoric acid. 9,9-Dimethyl-7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-one was reduced to 9,9-dimethyl-7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-ol with sodium tetrahydridoborate.

  DOI：

  10.1134/s1070428010120134
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 溶剂黄146 作用下， 反应 3.0h， 生成 5,5-dimethyl-3,4,5,6-tetrahydro-3-benz[c]phenanthridinone
  参考文献：
  名称：

  Synthesis of new benzo[c]phenanthridine derivatives

  摘要：

  Three-component condensation of naphthalen-1-amine with triethyl orthoformate and dimedone or cyclopentane-1,3-dione, as well as the reaction of naphthalen-1-amine with 2-acetyl-5,5-dimethylcyclohexane-1,3-dione, gave the corresponding 2-[1-(alpha-naphthylamino)alkylidene]cycloalkane-1,3-diones which underwent intramolecular cyclization to 7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-one derivatives on heating in polyphosphoric acid. 9,9-Dimethyl-7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-one was reduced to 9,9-dimethyl-7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-ol with sodium tetrahydridoborate.

  DOI：

  10.1134/s1070428010120134

文献信息

• Synthesis of tetrahydrobenzophenanthridinones.<b>V</b>
  作者：Roberto Martínez、Rubén A. Toscano、Irma E. Linzaga、Hanani Sánchez

  DOI：10.1002/jhet.5570290603

  日期：1992.10

  The preparation of tetrahydrobenzophenanthridinones 4 and 5, potential useful intermediates for the synthesis of Dynemicin A models, is described. The structure of all products was corroborated by ir, 1H-nmr, ms and X-ray spectroscopy.

  描述了四氢二苯并菲基吡啶酮4和5的制备方法，这是合成Dynemicin A模型的潜在有用中间体。红外，1 H-nmr，ms和X射线光谱证实了所有产品的结构。
• Unusual Formation of 2-Aryl-7,7-dimethyl-6,8-epidiseleno-5,6,7,8-tetrahydro-5-quinazolones
  作者：Natalija Tonkikh、Helmut Duddeck、Marina Petrova、Ojars Neilands、Andris Strakovs

  DOI：10.1002/(sici)1099-0690(199907)1999:7<1585::aid-ejoc1585>3.0.co;2-f

  日期：1999.7

  The selenious acid oxidation of 2-aryl-7,7-dimethyl-5,6,7,8-tetrahydro-5-quinazolones 2a-c leads to the corresponding 2-aryl-7,7-dimethyl-6,8-epidiseleno-5,6, 7,8-tetrahydro-5-quinazolones 3a-c. This is the first observation of the formation of an intramolecular unsymmetrical diselenide by selenious acid oxidation and reports the first derivatives of the new ring system 2,3-diselenabicyclo[3.2.1]octane.
• Synthesis of new benzo[c]phenanthridine derivatives
  作者：A. N. Pyrko

  DOI：10.1134/s1070428010120134

  日期：2010.12

  Three-component condensation of naphthalen-1-amine with triethyl orthoformate and dimedone or cyclopentane-1,3-dione, as well as the reaction of naphthalen-1-amine with 2-acetyl-5,5-dimethylcyclohexane-1,3-dione, gave the corresponding 2-[1-(alpha-naphthylamino)alkylidene]cycloalkane-1,3-diones which underwent intramolecular cyclization to 7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-one derivatives on heating in polyphosphoric acid. 9,9-Dimethyl-7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-one was reduced to 9,9-dimethyl-7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-ol with sodium tetrahydridoborate.