2-hydroxy-3(γ-chloropropyl)-1,4-naphthoquinone | 114521-74-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-3(γ-chloropropyl)-1,4-naphthoquinone
• 英文别名: 2-oxy-3-(3'-chloropropyl)-1,4-naphthoquinone；2-(3-chloro-propyl)-3-hydroxy-[1,4]naphthoquinone；2-(3-Chlor-propyl)-3-hydroxy-[1,4]naphthochinon
• CAS: 114521-74-3
• 化学式: C₁₃H₁₁ClO₃
• 分子量: 250.682
• InChiKey: UNESMTJFVWTKIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3(γ-chloropropyl)-1,4-naphthoquinone 、 乙醛 在 boron trichloride-diethyl ether 作用下， 生成 2-Acetoxy-3-(3'-chlorpropyl)-1,4-naphthochinon
  参考文献：
  名称：

  Synthesis of 2-chloroalkyl-1,4-naphthoquinones and their reactivity in the formation of autocomplexes

  摘要：

  A series of the chloroalkyl derivatives of 1,4-naphtoquinone were synthesized and the electronic absorption spectra in 200-350 nm of these compounds were studied with the purpose of obtaining autocomplexes. The electronic absorption spectra of 1,4-naphtoquinones are characterized by four pi-pi* bands which have different sensitivity of lambda(max) to the electronic effects of the substituents. Some of the rules of the substituent influence on the spectral characteristics were found. Both steric factors, such as the formation of the cyclic structures due to the local interaction between the chloroethyl and chloropropyl radicals and the carbonyl of the quinone ring, and electronic effects, such as the insufficient delocalization of the extra change in -CH2-CH2+ leading to the poor stability of the carbocation, encumber the course of the reaction of complex formation.

  DOI：

  10.1016/0584-8539(95)01517-5
• 作为产物：
  描述：

  2-羟基-1,4-萘醌 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙醚 、 溶剂黄146 作用下， 生成 2-hydroxy-3(γ-chloropropyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Naphthoquinone Antimalarials. XXVI.¹ Thioether Naphthoquinones²

  摘要：

  DOI：

  10.1021/ja01168a015

文献信息

• Prezhdo, V. V.; Bogunets, N. P.; Chaikovskaya, V. A., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 7, p. 1366 - 1372
  作者：Prezhdo, V. V.、Bogunets, N. P.、Chaikovskaya, V. A.、Shevchenko, T. N.、Surov, Yu. N.

  DOI：——

  日期：——