3,7-dimethyl-5-hydroxyindole | 196616-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,7-dimethyl-5-hydroxyindole
• 英文别名: 3,7-dimethyl-1H-indol-5-ol
• CAS: 196616-58-7
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: OBPJOFCSWRNVDD-UHFFFAOYSA-N

物化性质

• 沸点：
  350.2±37.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,7-dimethyl-5-hydroxyindole 在 potassium dihydrogenphosphate 、 potassium nitrososulfonate 作用下， 以 水 、 乙腈 为溶剂， 以76%的产率得到3,7-二甲基-1H-吲哚-4,5-二酮
  参考文献：
  名称：

  Synthesis, Physicochemical Properties, and Amine-Oxidation Reaction of Indolequinone Derivatives as Model Compounds of Novel Organic Cofactor TTQ of Amine Dehydrogenases

  摘要：

  3,4-Disubstituted 6,7-indolequinones [1,3-dimethyl-4-(3'-methylindol-2'-yl)indole-6,7-dione (2), 3-methyl-4-phenylindole-6,7-dione (3), and 3,4-dimethyl-6,7-dione (4)] and a 3,7-disubstituted 4,5-indolequinone [3,7-dimethylindole-4,5-dione (5)] have been synthesized as models for the novel organic cofactor TTQ of bacterial amine dehydrogenases. The substituent and structural effects on the physicochemical properties of the quinones have been investigated in detail by comparing the spectroscopic data (UV-vis, IR, H-1- and C-13-NMR), pK(a) values of the pyrrole proton, and the two-electron redox potentials with those of model compound 1 [3-methyl-4-(3'-methylindol-2'-yl)indole-6,7-dione] previously reported (ref 5). Reactivity of each quinone in the transamination process [iminoquinone formation (k(1)), rearrangement to product-imine (k(2)), and aminophenol formation (k(3))] has been investigated kinetically, revealing that the substituent and structural effects on the amine-oxidation reaction are not so significant. In the aerobic catalytic oxidation of benzylamine, however, the aromatic substituents on the quinone ring play an important role to protect the quinone from the deactivation process of a Michael-type addition by the amine, making it act as an efficient turnover catalyst.

  DOI：

  10.1021/jo970716l
• 作为产物：
  描述：

  4-(苄氧基)-2-甲基苯胺 在 palladium on activated charcoal 氢氧化钾 、 CuO/Cr₂O₃ 、 氢气 作用下， 以 喹啉 、 甲醇 、 水 、 乙腈 为溶剂， 60.0~200.0 ℃ 、405.3 kPa 条件下， 反应 14.0h， 生成 3,7-dimethyl-5-hydroxyindole
  参考文献：
  名称：

  Synthesis, Physicochemical Properties, and Amine-Oxidation Reaction of Indolequinone Derivatives as Model Compounds of Novel Organic Cofactor TTQ of Amine Dehydrogenases

  摘要：

  3,4-Disubstituted 6,7-indolequinones [1,3-dimethyl-4-(3'-methylindol-2'-yl)indole-6,7-dione (2), 3-methyl-4-phenylindole-6,7-dione (3), and 3,4-dimethyl-6,7-dione (4)] and a 3,7-disubstituted 4,5-indolequinone [3,7-dimethylindole-4,5-dione (5)] have been synthesized as models for the novel organic cofactor TTQ of bacterial amine dehydrogenases. The substituent and structural effects on the physicochemical properties of the quinones have been investigated in detail by comparing the spectroscopic data (UV-vis, IR, H-1- and C-13-NMR), pK(a) values of the pyrrole proton, and the two-electron redox potentials with those of model compound 1 [3-methyl-4-(3'-methylindol-2'-yl)indole-6,7-dione] previously reported (ref 5). Reactivity of each quinone in the transamination process [iminoquinone formation (k(1)), rearrangement to product-imine (k(2)), and aminophenol formation (k(3))] has been investigated kinetically, revealing that the substituent and structural effects on the amine-oxidation reaction are not so significant. In the aerobic catalytic oxidation of benzylamine, however, the aromatic substituents on the quinone ring play an important role to protect the quinone from the deactivation process of a Michael-type addition by the amine, making it act as an efficient turnover catalyst.

  DOI：

  10.1021/jo970716l

文献信息

• Synthesis, Physicochemical Properties, and Amine-Oxidation Reaction of Indolequinone Derivatives as Model Compounds of Novel Organic Cofactor TTQ of Amine Dehydrogenases
  作者：Shinobu Itoh、Naoki Takada、Takeya Ando、Shigenobu Haranou、Xin Huang、Yasushi Uenoyama、Yoshiki Ohshiro、Mitsuo Komatsu、Shunichi Fukuzumi

  DOI：10.1021/jo970716l

  日期：1997.8.1

  3,4-Disubstituted 6,7-indolequinones [1,3-dimethyl-4-(3'-methylindol-2'-yl)indole-6,7-dione (2), 3-methyl-4-phenylindole-6,7-dione (3), and 3,4-dimethyl-6,7-dione (4)] and a 3,7-disubstituted 4,5-indolequinone [3,7-dimethylindole-4,5-dione (5)] have been synthesized as models for the novel organic cofactor TTQ of bacterial amine dehydrogenases. The substituent and structural effects on the physicochemical properties of the quinones have been investigated in detail by comparing the spectroscopic data (UV-vis, IR, H-1- and C-13-NMR), pK(a) values of the pyrrole proton, and the two-electron redox potentials with those of model compound 1 [3-methyl-4-(3'-methylindol-2'-yl)indole-6,7-dione] previously reported (ref 5). Reactivity of each quinone in the transamination process [iminoquinone formation (k(1)), rearrangement to product-imine (k(2)), and aminophenol formation (k(3))] has been investigated kinetically, revealing that the substituent and structural effects on the amine-oxidation reaction are not so significant. In the aerobic catalytic oxidation of benzylamine, however, the aromatic substituents on the quinone ring play an important role to protect the quinone from the deactivation process of a Michael-type addition by the amine, making it act as an efficient turnover catalyst.