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5-溴-1H-异苯并吡喃-1-酮 | 245677-36-5

中文名称
5-溴-1H-异苯并吡喃-1-酮
中文别名
——
英文名称
5-bromoisocoumarin
英文别名
5-bromo-1H-isochromen-1-one;5-bromoisochromen-1-one
5-溴-1H-异苯并吡喃-1-酮化学式
CAS
245677-36-5
化学式
C9H5BrO2
mdl
——
分子量
225.041
InChiKey
WHYKRNIHXWPVRG-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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

SDS

SDS:16251e866d2819516e59a1190fc4a903
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上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
    —— 5-aminoisocoumarin 70758-25-7 C9H7NO2 161.16

反应信息

  • 作为反应物:
    描述:
    5-溴-1H-异苯并吡喃-1-酮 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
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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.
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