5-溴-1H-异苯并吡喃-1-酮 | 245677-36-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 中文名称: 5-溴-1H-异苯并吡喃-1-酮
• 英文名称: 5-bromoisocoumarin
• 英文别名: 5-bromo-1H-isochromen-1-one；5-bromoisochromen-1-one
• CAS: 245677-36-5
• 化学式: C₉H₅BrO₂
• 分子量: 225.041
• InChiKey: WHYKRNIHXWPVRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  5-溴-1H-异苯并吡喃-1-酮 在 氨 作用下， 以 乙二醇甲醚 为溶剂， 反应 8.0h， 以71%的产率得到5-溴-1(2H)-异喹啉酮
  参考文献：
  名称：

  2-Nitroimidazol-5-ylmethyl as a potential bioreductively activated prodrug system: reductively triggered release of the parp inhibitor 5-bromoisoquinolinone

  摘要：

  5-Chloromethyl-1-methyl-2-nitroimidazole reacted efficiently with the anion derived from 5-bromo-isoquinolin-1-one to give 5-bromo-2-((1-methyl-2-nitroimidazol-5-yl)methyl)isoquinolin-1-one. Biomimetic reduction effected release of the 5-bromoisoquinolin-1-one. The 2-nitroimidazol-5-ylmethyl unit thus has potential for development as a general prodrug system for selective drug delivery to hypoxic tissues. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00306-6
• 作为产物：
  描述：

  5-硝基-1H-异色烯-1-酮 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 、 potassium bromide 、 copper(I) bromide 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 5-溴-1H-异苯并吡喃-1-酮
  参考文献：
  名称：

  2-Nitroimidazol-5-ylmethyl as a potential bioreductively activated prodrug system: reductively triggered release of the parp inhibitor 5-bromoisoquinolinone

  摘要：

  5-Chloromethyl-1-methyl-2-nitroimidazole reacted efficiently with the anion derived from 5-bromo-isoquinolin-1-one to give 5-bromo-2-((1-methyl-2-nitroimidazol-5-yl)methyl)isoquinolin-1-one. Biomimetic reduction effected release of the 5-bromoisoquinolin-1-one. The 2-nitroimidazol-5-ylmethyl unit thus has potential for development as a general prodrug system for selective drug delivery to hypoxic tissues. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00306-6

文献信息

• N- and O-Alkylation of isoquinolin-1-ones in the Mitsunobu reaction: development of potential drug delivery systems
  作者：Sandra Ferrer、Declan P. Naughton、Ifat Parveen、Michael D. Threadgill

  DOI：10.1039/b109776h

  日期：2002.1.23

  Regioselective methods were investigated to prepare N- and O-alkylated isoquinolin-1-ones efficiently. The predicted regioselective alkylation of the nitrogen with (hetero)benzyl halides was complemented using (hetero)benzylic Mitsunobu electrophiles to alkylate predominantly at the oxygen. A series of drug-delivery conjugates was prepared demonstrating control over the site of alkylation. The Mitsunobu reaction provides a new approach to 1-alkoxyisoquinolines that were unavailable via previous harsher synthetic methods.

  研究了区域选择性方法，以高效制备N-和O-烷基化的异喹啉-1-酮。通过使用（杂）苄基 Mitsunobu 亲电试剂，补充了氮的区域选择性烷基化，主要在氧处进行烷基化。制备了一系列药物输送偶联物，展示了烷基化位点的控制。Mitsunobu 反应为通过先前较为苛刻的合成方法无法获得的1-烷氧基异喹啉提供了一种新途径。
• 2-Nitroimidazol-5-ylmethyl as a potential bioreductively activated prodrug system: reductively triggered release of the parp inhibitor 5-bromoisoquinolinone
  作者：Ifat Parveen、Declan P Naughton、William J.D Whish、Michael D Threadgill

  DOI：10.1016/s0960-894x(99)00306-6

  日期：1999.7

  5-Chloromethyl-1-methyl-2-nitroimidazole reacted efficiently with the anion derived from 5-bromo-isoquinolin-1-one to give 5-bromo-2-((1-methyl-2-nitroimidazol-5-yl)methyl)isoquinolin-1-one. Biomimetic reduction effected release of the 5-bromoisoquinolin-1-one. The 2-nitroimidazol-5-ylmethyl unit thus has potential for development as a general prodrug system for selective drug delivery to hypoxic tissues. (C) 1999 Elsevier Science Ltd. All rights reserved.