1-bromo-2-(bromomethyl)-4-(dimethylamino)benzene | 163914-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-bromo-2-(bromomethyl)-4-(dimethylamino)benzene
• 英文别名: 2-bromo-5-(N,N-dimethylamino)benzyl bromide；4-bromo-3-(bromomethyl)-N,N-dimethylaniline；1-Bromo-2-bromomethyl-4-dimethylaminobenzene
• CAS: 163914-14-5
• 化学式: C₉H₁₁Br₂N
• 分子量: 293.001
• InChiKey: HQGBZABSGLHNSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-bromo-2-(bromomethyl)-4-(dimethylamino)benzene 在 4-二甲氨基吡啶 potassium tert-butylate 、 叔丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 1.25h， 生成 (2E)-2-[1-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]propan-2-ylidene]-5-(dimethylamino)-3H-inden-1-one
  参考文献：
  名称：

  Preparation of E-(2-substituted-1-methylethylidene)indanones derived from monic acid

  摘要：

  Alkylation of the lithium dienolate of the monic acid hydroxamate (3) with o-bromo(bromomethyl) benzene or heteroaromatic derivatives gave alpha-alkylated products (5). This alkylation procedure wa surprisingly catalysed by 4-dimethylaminopyridine. Metal-halogen exchange with t-butyl lithium occurred with concomitant intramolecular cyclisation to give a mixture of the deconjugated ketones (6). Reconjugation with potassium t-butoxide stereoselectively produced with the E-isomer (7). Deprotection gave the monic acid derived ketone (1).

  DOI：

  10.1016/s0040-4039(00)73095-4
• 作为产物：
  描述：

  2-溴-5-(二甲基氨基)苯甲酸甲酯 在 溴 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-bromo-2-(bromomethyl)-4-(dimethylamino)benzene
  参考文献：
  名称：

  Preparation of E-(2-substituted-1-methylethylidene)indanones derived from monic acid

  摘要：

  Alkylation of the lithium dienolate of the monic acid hydroxamate (3) with o-bromo(bromomethyl) benzene or heteroaromatic derivatives gave alpha-alkylated products (5). This alkylation procedure wa surprisingly catalysed by 4-dimethylaminopyridine. Metal-halogen exchange with t-butyl lithium occurred with concomitant intramolecular cyclisation to give a mixture of the deconjugated ketones (6). Reconjugation with potassium t-butoxide stereoselectively produced with the E-isomer (7). Deprotection gave the monic acid derived ketone (1).

  DOI：

  10.1016/s0040-4039(00)73095-4

文献信息

• Antiangiogenic versus cytotoxic activity in analogues of aeroplysinin-1
  作者：Rubén Córdoba、Nélida Salvador Tormo、Antonio Fernández Medarde、Joaquín Plumet

  DOI：10.1016/j.bmc.2007.05.011

  日期：2007.8

  A series of analogues of the potentially angiogenic inhibitor aeroplysinin-l 1 were synthesized and their in vitro antiangiogenic and cytotoxic activities evaluated. In the case of epoxy ketone 6 and azlactone 36 the relationship sprouting inhibition assayl cytotoxicity in BAE cells was enhanced by one order and two orders of magnitude, respectively, with respect to the reference. These results imply more specific antiangiogenic properties for the synthesized derivatives. (c) 2007 Elsevier Ltd. All rights reserved.
• (HETERO)-ARYL KETONES DERIVATIVES WITH ANTIBACTERIAL PROPERTIES
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0652875A1

  公开（公告）日：1995-05-17
• US5536745A
  申请人：——

  公开号：US5536745A

  公开（公告）日：1996-07-16
• [EN] (HETERO)-ARYL KETONES DERIVATIVES WITH ANTIBACTERIAL PROPERTIES<br/>[FR] DERIVES DE CETONES D'(HETERO)-ARYLE A CARACTERISTIQUES ANTIBACTERIENNES
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1994002478A1

  公开（公告）日：1994-02-03

  (EN) Conformationally restricted aryl and heteroaryl ketones derived from monic acid have useful antibacterial properties.(FR) Des cétones d'aryle et d'hétéroaryle à structure restreinte, dérivées d'acide monique, présentent des caractéristiques antibactériennes.
• Preparation of E-(2-substituted-1-methylethylidene)indanones derived from monic acid
  作者：Neil D. Pearson、Nigel J.P. Broom、Peter J. O'Hanlon

  DOI：10.1016/s0040-4039(00)73095-4

  日期：1994.5

  Alkylation of the lithium dienolate of the monic acid hydroxamate (3) with o-bromo(bromomethyl) benzene or heteroaromatic derivatives gave alpha-alkylated products (5). This alkylation procedure wa surprisingly catalysed by 4-dimethylaminopyridine. Metal-halogen exchange with t-butyl lithium occurred with concomitant intramolecular cyclisation to give a mixture of the deconjugated ketones (6). Reconjugation with potassium t-butoxide stereoselectively produced with the E-isomer (7). Deprotection gave the monic acid derived ketone (1).