2-溴-1-(溴甲基)-3,4-二甲氧基苯 | 147912-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-溴-1-(溴甲基)-3,4-二甲氧基苯
• 英文名称: 2-Bromo-1-(bromomethyl)-3,4-dimethoxybenzene
• CAS: 147912-63-8
• 化学式: C₉H₁₀Br₂O₂
• 分子量: 309.985
• InChiKey: WEWGUPGEALYFMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-溴-1-(溴甲基)-3,4-二甲氧基苯 在 lithium hydroxide 、 potassium phosphate 、 lead(II) nitrate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 36.0h， 生成 3-(9-phenylfluoren-9-yl)-4-<(2-bromo-3,4-dimethoxyphenyl)methyl>oxazolidin-5-one
  参考文献：
  名称：

  Synthesis of 2-[N-(9-phenylfluoren-9-yl)amino]-1-indanones by anionic cyclization of phenylalanine-derived oxazolidinones

  摘要：

  A novel preparation of N-(phenylfluorenyl)-2-amino-1-indanones is described. The key step is the cyclization of aryl-substituted o-bromophenylalanine-derived oxazolidinones with n-BuLi by halogen-metal exchange followed by in situ intramolecular acylation of the aryllithium intermediate. When this method was applied to an optically pure oxazolidinone derived from an amino acid, cyclization occurred with complete retention of the integrity of the chiral center.

  DOI：

  10.1021/jo00062a018

文献信息

• A Concise Synthesis of Mono- and Polysubstituted and Diversely N-Function­alized Isoindolinones and Isoquinolones
  作者：Axel Couture、Magali Lorion、Eric Deniau、Pierre Grandclaudon

  DOI：10.1055/s-2008-1067125

  日期：——

  A variety of differently substituted and diversely N-(sulfanyl)hydroxyalkyl functionalized isoindolinones and isoquinol­ones have been obtained by anionic cyclization of cyclic bromobenzyl or bromophenethylcarbamates and thiocarbamates.

  已通过环状溴苄基或溴苯乙基氨基甲酸酯及硫氨基甲酸酯的阴离子环化反应，获得了多种不同取代和多样化N-(硫基)羟基烷基官能化的异吲哚酮和异喹啉酮。
• Intramolecular Heck reaction strategy for the synthesis of functionalised tetrahydroanthracenes: a facile formal total synthesis of the linear abietane diterpene, umbrosone
  作者：Sujaya Sengupta、Ranjan Mukhopadhyay、Basudeb Achari、Asish Kr. Banerjee

  DOI：10.1016/j.tetlet.2005.01.021

  日期：2005.2

  Rapid annulation employing an intramolecular Heck reaction yielded the functionalised 1,1,10-trimethyl-6-methoxy-1,2,3,4-tetrahydroanthracene 4a, a key intermediate for the linear diterpenoid quinone umbrosone (1), and the related compounds 4b-d. A similar strategy was also successfully adopted for the synthesis of the 9-methyl tetrahydroanthracene ester 5 and the tetrahydrodibenzo[a,d]cycloheptene ester 6. (C) 2005 Elsevier Ltd. All rights reserved.
• Paleo M. Rita, Castedo Luis, Dominguez Domingo, J. Org. Chem., 58 (1993) N 10, S 2763-2767
  作者：Paleo M. Rita, Castedo Luis, Dominguez Domingo

  DOI：——

  日期：——
• Synthesis of 2-[N-(9-phenylfluoren-9-yl)amino]-1-indanones by anionic cyclization of phenylalanine-derived oxazolidinones
  作者：M. Rita Paleo、Luis Castedo、Domingo Dominguez

  DOI：10.1021/jo00062a018

  日期：1993.5

  A novel preparation of N-(phenylfluorenyl)-2-amino-1-indanones is described. The key step is the cyclization of aryl-substituted o-bromophenylalanine-derived oxazolidinones with n-BuLi by halogen-metal exchange followed by in situ intramolecular acylation of the aryllithium intermediate. When this method was applied to an optically pure oxazolidinone derived from an amino acid, cyclization occurred with complete retention of the integrity of the chiral center.