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3,5-diacetoxy-2-bromo-[1,4]naphthoquinone | 161621-00-7

中文名称
——
中文别名
——
英文名称
3,5-diacetoxy-2-bromo-[1,4]naphthoquinone
英文别名
3,5-Diacetoxy-2-brom-[1,4]naphthochinon
3,5-diacetoxy-2-bromo-[1,4]naphthoquinone化学式
CAS
161621-00-7
化学式
C14H9BrO6
mdl
——
分子量
353.126
InChiKey
KMXWDGXMJMSPFZ-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):
    2.16
  • 重原子数:
    21.0
  • 可旋转键数:
    2.0
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.14
  • 拓扑面积:
    86.74
  • 氢给体数:
    0.0
  • 氢受体数:
    6.0

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

反应信息

  • 作为反应物:
    描述:
    3,5-diacetoxy-2-bromo-[1,4]naphthoquinone(2-三甲基stannanyl-苯基)-carbamic acid 叔丁酯四(三苯基膦)钯 、 copper(I) bromide 作用下, 以 1,4-二氧六环 为溶剂, 反应 6.0h, 以60%的产率得到2-<2-<(tert-Butoxycarbonyl)amino>phenyl>-3,5-bis(acetyloxy)-1,4-naphthoquinone
    参考文献:
    名称:
    Synthesis of Antibiotics WS 5995 A and C and Related Compounds by Palladium-Catalyzed Coupling of 2-Bromonaphthoquinones with Organostannanes
    摘要:
    The synthesis of arylnaphthoquinones can be performed simply by using as the key reaction the Pd(0)- and Cu(I)-catalyzed coupling of arylstannanes with 2-bromonaphthoquinones as the electrophiles. The palladium-catalyzed coupling reaction is general and allows for the functionalization of the unprotected quinone nucleus with alkyl, alkenyl, and aryl substituents. The coupling process tolerates the presence of a chelated peri hydroxyl and steric crowding of a 2,6-disubstituted arylstannane, although the preparation of a 2,6,2',6'-tetrasubstituted biaryl by coupling of 2-bromo-3,5-bis(acetyloxy)-1,4-naphthoquinone as the electrophile with 2,6-disubstituted arylstannanes was unsuccessful. The syntheses of quinonoid antibiotics WS 5995 A and C was accomplished by using this method as the key step. Benz[b]phenanthridinone 1, hypothetical intermediate in the biosynthesis of benz[b]phenanthridine alkaloids, was also prepared from antibiotic WS 5995 C or by addition of ammonia to the 2-aryl-1,4-naphthoquinone 41 followed by heterocyclization.
    DOI:
    10.1021/jo00099a045
  • 作为产物:
    参考文献:
    名称:
    Synthesis of Antibiotics WS 5995 A and C and Related Compounds by Palladium-Catalyzed Coupling of 2-Bromonaphthoquinones with Organostannanes
    摘要:
    The synthesis of arylnaphthoquinones can be performed simply by using as the key reaction the Pd(0)- and Cu(I)-catalyzed coupling of arylstannanes with 2-bromonaphthoquinones as the electrophiles. The palladium-catalyzed coupling reaction is general and allows for the functionalization of the unprotected quinone nucleus with alkyl, alkenyl, and aryl substituents. The coupling process tolerates the presence of a chelated peri hydroxyl and steric crowding of a 2,6-disubstituted arylstannane, although the preparation of a 2,6,2',6'-tetrasubstituted biaryl by coupling of 2-bromo-3,5-bis(acetyloxy)-1,4-naphthoquinone as the electrophile with 2,6-disubstituted arylstannanes was unsuccessful. The syntheses of quinonoid antibiotics WS 5995 A and C was accomplished by using this method as the key step. Benz[b]phenanthridinone 1, hypothetical intermediate in the biosynthesis of benz[b]phenanthridine alkaloids, was also prepared from antibiotic WS 5995 C or by addition of ammonia to the 2-aryl-1,4-naphthoquinone 41 followed by heterocyclization.
    DOI:
    10.1021/jo00099a045
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文献信息

  • STUDIES IN THE JUGLONE SERIES. II. HYDROXY AND HYDROXYHALOGENO DERIVATIVES
    作者:R. H. THOMSON
    DOI:10.1021/jo01164a015
    日期:1948.11
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