EOPZ | 94437-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: EOPZ
• 英文别名: 2-ethoxypromazine；[3-(2-ethoxy-phenothiazin-10-yl)-propyl]-dimethyl-amine；[3-(2-Aethoxy-phenothiazin-10-yl)-propyl]-dimethyl-amin；3-Aethoxy-10-<3-dimethylamino-propyl>-phenothiazin
• CAS: 94437-15-7
• 化学式: C₁₉H₂₄N₂OS
• 分子量: 328.478
• InChiKey: VMZKGIGWULRWJT-UHFFFAOYSA-N

物化性质

• 沸点：
  473.2±45.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  15.71
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  乙醇 、 盐酸氯丙嗪 以66%的产率得到盐酸丙嗪
  参考文献：
  名称：

  Photodegradation of 2-chloro Substituted Phenothiazines in Alcohols

  摘要：

  AbstractThe mechanisms that trigger the phototoxic response to 2‐chlorophenothiazine derivatives are still unknown. To better understand the relationship between the molecular structure of halogenated phenothiazines and their phototoxic activity, their photophysics and photochemistry were studied in several alcohols. The photodestruction quantum yields were determined under anaerobic conditions using monochromatic light (313 nm). Absorption‐ and emission‐spectroscopy, 1H‐ and 13C‐NMR and GC‐MS were used to characterize the photoproducts and reference compounds. An electron transfer mechanism had been previously proposed by Bunce et al. (J. Med. Chem. 22, 202–204) to explain the large difference between the photodestruction quantum yield of 2‐chlorpromazine (ϕ = 0.46) and 2‐chlorphenothiazine (ϕ = 0.20). According to these authors, the alkylamino chain transfers an electron to the phenothiazine moiety. Our results demonstrate that this mechanism is incorrect, because the photodestruction quantum yields of all chlorinated derivatives of this study are the same under the same conditions of solvent and irradiation wavelength. The quantum yield has no dependence on the 10‐substituent, but it depends on the solvent. The percentage of each photoproduct, on the other hand, strongly depends on that substituent, but not very much on the solvent. Finally, it is demonstrated that the phototoxic effect of chlorinated phenothiazines is not related to the photodechlorination, although both processes share the same transient.

  DOI：

  10.1111/j.1751-1097.2008.00412.x

文献信息

• Photodegradation of 2-chloro Substituted Phenothiazines in Alcohols
  作者：Carmelo García、Luis Piñero、Rolando Oyola、Rafael Arce

  DOI：10.1111/j.1751-1097.2008.00412.x

  日期：2009.1

  AbstractThe mechanisms that trigger the phototoxic response to 2‐chlorophenothiazine derivatives are still unknown. To better understand the relationship between the molecular structure of halogenated phenothiazines and their phototoxic activity, their photophysics and photochemistry were studied in several alcohols. The photodestruction quantum yields were determined under anaerobic conditions using monochromatic light (313 nm). Absorption‐ and emission‐spectroscopy, 1H‐ and 13C‐NMR and GC‐MS were used to characterize the photoproducts and reference compounds. An electron transfer mechanism had been previously proposed by Bunce et al. (J. Med. Chem. 22, 202–204) to explain the large difference between the photodestruction quantum yield of 2‐chlorpromazine (ϕ = 0.46) and 2‐chlorphenothiazine (ϕ = 0.20). According to these authors, the alkylamino chain transfers an electron to the phenothiazine moiety. Our results demonstrate that this mechanism is incorrect, because the photodestruction quantum yields of all chlorinated derivatives of this study are the same under the same conditions of solvent and irradiation wavelength. The quantum yield has no dependence on the 10‐substituent, but it depends on the solvent. The percentage of each photoproduct, on the other hand, strongly depends on that substituent, but not very much on the solvent. Finally, it is demonstrated that the phototoxic effect of chlorinated phenothiazines is not related to the photodechlorination, although both processes share the same transient.