2-chloro-5-methoxy-4,6-dimethylindanone | 134379-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-chloro-5-methoxy-4,6-dimethylindanone
• 英文别名: 2-chloro-5-methoxy-4,6-dimethylindan-1-one；2-Chloro-5-methoxy-4,6-dimethyl-2,3-dihydroinden-1-one
• CAS: 134379-27-4
• 化学式: C₁₂H₁₃ClO₂
• 分子量: 224.687
• InChiKey: BZHDSZMSBUABEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-5-methoxy-4,6-dimethylindanone 在 potassium tert-butylate 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 5,6-dihydro-3-hydroxy-2,4-dimethylindeno<2,1-b>indole
  参考文献：
  名称：

  New antioxidants incorporating indole and indoline chromophores

  摘要：

  Syntheses of potent antioxidants utilising indenoindole or indenoindoline pharmacophores are described. The antioxidant behaviour and the oxidation potentials of these compounds are correlated, and some of their reactions with radicals are noted.

  DOI：

  10.1016/s0040-4020(01)87108-8
• 作为产物：
  描述：

  5-甲氧基-4,6-二甲基-1-茚满酮 在 磺酰氯 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以14%的产率得到2,2-Dichloro-5-methoxy-4,6-dimethyl-indan-1-one
  参考文献：
  名称：

  New antioxidants incorporating indole and indoline chromophores

  摘要：

  Syntheses of potent antioxidants utilising indenoindole or indenoindoline pharmacophores are described. The antioxidant behaviour and the oxidation potentials of these compounds are correlated, and some of their reactions with radicals are noted.

  DOI：

  10.1016/s0040-4020(01)87108-8

文献信息

• Indenoindole compounds I
  申请人：UNIVERSITY OF BATH

  公开号：EP0404536A1

  公开（公告）日：1990-12-27

  Compounds of the formula wherein R is hydrogen or a lower alkyl group, R¹ and R² are independently selected from hydrogen or a lower alkyl group, R³, R⁴ and R⁶ are independently selected from hydrogen, halogen or a lower alkyl group, R⁵ is hydrogen, hydroxy, halogen, a lower alkyl group, a lower alkoxy group, a mono- or di-lower alkylamino group, NH₂ or NR¹¹ COR¹², R⁷, R⁸, R⁹ and R¹⁰ are independently selected from hydrogen, hydroxy, a lower alkyl group, a lower alkoxy group, a mono- or di-lower alkylamino group, NH₂ or NR¹¹ COR¹², R¹¹ is a hydrogen or a lower alkyl group, R¹² is a lower alkyl group, with the proviso that when R is hydrogen then at least one of the substituents R¹ to R¹⁰ is not hydrogen, or a salt thereof, are useful as antioxidants, within the medical and non medical field, and that when R is hydrogen, methyl or neopentyl in formula IA, then at least one of R¹ to R¹⁰ is not hydrogen. Many of the compounds of formula IA and IB are new and various methods for preparing them are described.

  式中的化合物 其中 R 是氢或低级烷基、 R¹ 和 R² 独立选自氢或低级烷基，R³、R⁴ 和 R⁶ 独立选自氢、卤素或低级烷基、 R⁵ 是氢、羟基、卤素、低级烷基、低级烷氧基、单或双低级烷基氨基、NH₂ 或 NR¹¹ COR¹²、 R⁷、R⁸、R⁹ 和 R¹⁰ 独立选自氢、羟基、低级烷基、低级烷氧基、单或双低级烷基氨基、NH₂ 或 NR¹¹ COR¹²、 R¹¹ 是氢或低级烷基、 R¹² 是低级烷基、 但当 R 为氢时，R¹ 至 R¹⁰ 中至少有一个取代基不为氢，或其盐类在医疗和非医疗领域可用作抗氧化剂；当式 IA 中 R 为氢、甲基或新戊基时，R¹ 至 R¹⁰ 中至少有一个取代基不为氢。式 IA 和 IB 的许多化合物都是新化合物，并介绍了制备它们的各种方法。
• The synthesis of dihydroindenoindoles
  作者：Jeremy Graham、Aleyamma Ninan、Khalid Reza、Malcolm Sainsbury、Howard G. Shertzer

  DOI：10.1016/s0040-4020(01)80589-5

  日期：1992.1

  The Wender and Bischler indole syntheses have been investigated as potential routes to dihydroindenoindoles. Thus a Wender reaction between N,2-dilithio-N-trifluoroacetylaniline and 2-bromo-5-methoxy-4,6-dimethylindanone affords the corresponding dihydroindeno[1,2-b]indole. In general, however, indolisations of this type are limited to 2-halogenoindanones bearing electron donating groups conjugated with the carbonyl function since these depress enolate anion formation. When such groups are absent the products are N-trifluoroacetylaniline and compounds arising from deprotonation of the 2-halogenoindanones. This problem is offset, but not solved, if the reactions are carried out in the presence of cerium (III) chloride. In a Bischler reaction between 4-methoxyaniline and 2-bromoindanone both 8-methoxydihydroindeno[1,2-b]-indole and 9-methoxydihydroindeno[2,1-b]indole were formed in low yields, together with related pentacyclic compounds.
• US5185360A
  申请人：——

  公开号：US5185360A

  公开（公告）日：1993-02-09
• [EN] INDENOINDOLE COMPOUNDS
  申请人：UNIVERSITY OF BATH

  公开号：WO1990015800A1

  公开（公告）日：1990-12-27

  (EN) Compounds of formulae (IA) and (IB), wherein R is hydrogen or a lower alkyl group, R1 and R2 are independently selected from hydrogen or a lower alkyl group, R3, R4 and R6 are independently selected from hydrogen, halogen or a lower alkyl group, R5 is hydrogen, hydroxy, halogen, a lower alkyl group, a lower alkoxy group, a mono- or di-lower alkylamino group, NH2 or NR11 COR12, R7, R8, R9 and R10 are independently selected from hydrogen, hydroxy, a lower alkyl group, a lower alkoxy group, a mono- or di-lower alkylamino group, NH2 or NR11 COR12, R11 is a hydrogen or a lower alkyl group, R12 is a lower alkyl group, with the proviso that when R is hydrogen then at least one of the substituents R1 to R10 is not hydrogen, or a salt thereof, are useful as antioxidants, within the medical and non-medical field, and that when R is hydrogen, methyl or neopentyl in formula (IA), then at least one of R1 to R10 is not hydrogen. Many of the compounds of formulae (IA) and (IB) are new and various methods for preparing them are described.(FR) Composés selon les formules (IA) et (IB), dans lesquelles R représente l'hydrogène ou un groupe alkyle inférieur, R1 et R2 sont indépendamment choisis entre hydrogène ou un groupe alkyle inférieur R3, R4 et R6 sont choisis indépendamment entre hydrogène, halogène ou un groupe alkyle inférieur, R5 représente hydrogène, hydroxy, halogène, un groupe alkyle inférieur, un groupe alcoxy inférieur, un groupe mono- ou dialkylamino inférieur, NH2 ou NR11 COR12, R7, R8, R9 et R10 sont indépendamment choisis parmi hydrogène, hydroxy, un groupe alkyle inférieur, un groupe alcoxy inférieur, un groupe mono- ou dialkylamino inférieur, NH2 ou NR11 COR12, R11 représente un hydrogène ou un groupe alkyle inférieur, R12 représente un groupe alkyle inférieur, à condition que, lorsque R représente hydrogène, au moins un des substituants compris entre R1 et R10 ne représente pas hydrogène. Ces composés, ainsi qu'un de leurs sels, sont utiles en tant que antioxydants, dans les domaines médicaux et non médicaux. Lorsque R représente hydrogène, méthyle ou néopentyle dans la formule (IA), alors au moins un des éléments compris entre R1 et R10 ne représente pas hydrogène. Nombre des composés de la formule (IA) et $i(IB) sont nouveaux et l'on a mis point divers procédés permettant leur préparation.
• New antioxidants incorporating indole and indoline chromophores
  作者：David W Brown、Paul R Graupner、Malcolm Sainsbury、Howard G Shertzer

  DOI：10.1016/s0040-4020(01)87108-8

  日期：1991.1

  Syntheses of potent antioxidants utilising indenoindole or indenoindoline pharmacophores are described. The antioxidant behaviour and the oxidation potentials of these compounds are correlated, and some of their reactions with radicals are noted.