9,10-dihydro-9-methoxy-10-methyl-9-phenylacridine | 99682-60-7

• 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: 9,10-dihydro-9-methoxy-10-methyl-9-phenylacridine
• 英文别名: 9-methoxy-10-methyl-9-phenyl-9,10-dihydroacridine；9-phenyl-9-methoxy-10-methylacridine；9-methoxy-10-methyl-9-phenyl-9,10-dihydro-acridine；9-Methoxy-10-methyl-9-phenyl-9,10-dihydro-acridin；N-methyl-9-phenyl-9-methoxyacridane；9-methoxy-10-methyl-9-phenylacridine
• CAS: 99682-60-7
• 化学式: C₂₁H₁₉NO
• 分子量: 301.388
• InChiKey: AHOPJSYJDBCLIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,10-dihydro-9-methoxy-10-methyl-9-phenylacridine 生成 9-苯基-9-乙氧基-10-甲基吖啶
  参考文献：
  名称：

  Decker, Chemische Berichte, 1902, vol. 35, p. 3077

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基-蒽酮 在 苄基三乙基氯化铵 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 114.0h， 生成 9,10-dihydro-9-methoxy-10-methyl-9-phenylacridine
  参考文献：
  名称：

  Synthèse et activité antinociceptive de dérivés phényl-9-alkoxy-9 ou acyl-oxy-9 de xanthène, thioxanthène et acridine

  摘要：

  DOI：

  10.1016/0223-5234(89)90083-4

文献信息

• Thermal and Photochemical Reactions of 10-Methyl-9-phenylacridinium Chloride in Alcohols
  作者：Bin Zhou、Koji Kano、Shizunobu Hashimoto

  DOI：10.1246/bcsj.61.1633

  日期：1988.5

  The photoreduction of 10-methyl-9-phenylacridinium chloride in methanol containing K2CO3 involves the nucleophilic addition of methanol to the 9-position of the acridinium cation, the photoinduced heterolysis of the methanol adduct, and the hydride transfer from the alkoxide anion to the acridinium cation in the nonrelaxed ground states to give 9,10-dihydro-10-methyl-9-phenylacridine.

  10-甲基-9-苯基吖啶氯化物在含有 K2CO3 的甲醇中的光还原反应包括将甲醇亲核加成到吖啶阳离子的 9-位，甲醇加合物的光诱导异解，以及氢化物从醇盐阴离子转移到吖啶阳离子在非弛豫基态得到 9,10-二氢-10-甲基-9-苯基吖啶。
• Dibbens, Justin A.; Prager, Rolf H.; Schiesser, Carl H., Australian Journal of Chemistry, 1985, vol. 38, # 6, p. 913 - 920
  作者：Dibbens, Justin A.、Prager, Rolf H.、Schiesser, Carl H.、Wells, Andrew J.

  DOI：——

  日期：——
• Mechanistic Study of the Photochemical Hydroxide Ion Release from 9-Hydroxy-10-methyl-9-phenyl-9,10-dihydroacridine
  作者：Dapeng Zhou、Renat Khatmullin、Janitha Walpita、Nicholas A. Miller、Hoi Ling Luk、Shubham Vyas、Christopher M. Hadad、Ksenija D. Glusac

  DOI：10.1021/ja3031888

  日期：2012.7.18

  The excited-state behavior of 9-hydroxy-10-methyl-9-phenyl-9,10-dihydroacridine and its derivative, 9-methoxy-10-methyl-9-phenyl-9,10-dihydroacridine (AcrOR, R = H, Me), was studied via femtosecond and nanosecond UV-vis transient absorption spectroscopy. The solvent effects on C-O bond cleavage were clearly identified: a fast heterolytic cleavage (tau = 108 ps) was observed in protic solvents, while intersystem crossing was observed in aprotic solvents. Fast heterolysis generates 10methyl-9-phenylacridinium (Acr(+)) and -OH, which have a long recombination lifetime (no signal decay was observed within 100 mu s). AcrOH exhibits the characteristic behavior needed for its utilization as a chromophore in the pOH jump experiment.
• The generation of hydroxide and methoxide ions by photo-irradiation: use of aromatization to stabilize ionic photo-products from acridine derivatives
  作者：Aaron J. Ackmann、Jean M. J. Fréchet

  DOI：10.1039/cc9960000605

  日期：——

  The photolysis of 9-hydroxy-10-methyl-9-phenyl-9,10-dihydroacridine 1 or its 9-methoxy derivative 2 occurs with heterolytic cleavage of a C-O bond and formation of the desired strong base together with a cation that stabilizes itself through aromatization.
• NAGAO, YUKINORI;OYAMA, TSUKASA;ABE, YOSHIMOTO;MISONO, TAKAHISA, NIPPON KAGAKU KAJSI,(1988) N 1, 90-96
  作者：NAGAO, YUKINORI、OYAMA, TSUKASA、ABE, YOSHIMOTO、MISONO, TAKAHISA

  DOI：——

  日期：——