1-(溴甲基)苊 | 130800-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(溴甲基)苊
• 英文名称: 1-(Bromomethyl)acenaphthene
• 英文别名: 1-(Bromomethyl)-1,2-dihydroacenaphthylene
• CAS: 130800-06-5
• 化学式: C₁₃H₁₁Br
• 分子量: 247.134
• InChiKey: PYIHWZMKXKRUBB-UHFFFAOYSA-N

物化性质

• 沸点：
  373.1±11.0 °C(Predicted)
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  N-Cyclohexenylcyclohexanimine 、 1-(溴甲基)苊 生成 4H-cyclopentachrysene
  参考文献：
  名称：

  A new general synthesis of polycyclic aromatic compounds based on enamine chemistry

  摘要：

  Alkylation of enamines and enamine salts by benzylic and (beta-haloethyl)aryl halides, respectively, followed by acidic cyclodehydration and dehydrogenation provides an efficient synthetic approach to a wide range of polycyclic aromatic compounds of diverse structural types. Specific polycyclic hydrocarbons synthesized by this route include benzo[a]- and benzo[c]fluorene, 7H-dibenzo[c,g]-, 13H-dibenzo[a,i]-, and 13H-dibenzo[a,g]fluorene, 15H-tribenzo[a,c,i]fluorene, dibenzo[b,def]chrysene, benzo[rst]pentaphene, indeno[1,2-b]fluorene, fluoreno[3,4-c]fluorene, octahydrodibenz[a,j]anthracene, dibenz[a,j]anthracene, octahydrodibenz[a,h]anthracene, dibenz[a,h]anthracene, dibenz[a,h]anthracene, picene, benzo[c]picene, 1H-benz[bc]aceanthrylene, and 4H-cyclopenta[def]chrysene. This method with appropriate modifications appears to be potentially broader in scope than established traditional methods of polycyclic hydrocarbon synthesis.

  DOI：

  10.1021/jo00003a050
• 作为产物：
  描述：

  1-bromoacenaphthylene 在 palladium on activated charcoal sodium tetrahydroborate 、 正丁基锂 、 四甲基乙二胺 、 氢气 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 环己烷 为溶剂， -78.0~25.0 ℃ 、275.79 kPa 条件下， 反应 4.75h， 生成 1-(溴甲基)苊
  参考文献：
  名称：

  An Efficient Synthesis of 1-Substituted Acenaphthylenes and Acenaphthenes, Synthesis of Acenaphthene-1-carboxylic acid

  摘要：

  DOI：

  10.1021/jo00099a047

文献信息

• HARYEY, RONALD G.;PATAKI, JOHN;CORTEZ, CECILIA;DI, RADDO PASQUALE;YANG, C+, J. ORG. CHEM., 56,(1991) N, C. 1210-1217
  作者：HARYEY, RONALD G.、PATAKI, JOHN、CORTEZ, CECILIA、DI, RADDO PASQUALE、YANG, C+

  DOI：——

  日期：——
• Haddad Nizar, Abu-Shqara Elias, J. Org. Chem., 59 (1994) N 20, S 6090-6092
  作者：Haddad Nizar, Abu-Shqara Elias

  DOI：——

  日期：——
• An Efficient Synthesis of 1-Substituted Acenaphthylenes and Acenaphthenes, Synthesis of Acenaphthene-1-carboxylic acid
  作者：Nizar Haddad、Elias Abu-Shqara

  DOI：10.1021/jo00099a047

  日期：1994.10
• A new general synthesis of polycyclic aromatic compounds based on enamine chemistry
  作者：Ronald G. Harvey、John Pataki、Cecilia Cortez、Pasquale Di Raddo、Cheng Xi Yang

  DOI：10.1021/jo00003a050

  日期：1991.2

  Alkylation of enamines and enamine salts by benzylic and (beta-haloethyl)aryl halides, respectively, followed by acidic cyclodehydration and dehydrogenation provides an efficient synthetic approach to a wide range of polycyclic aromatic compounds of diverse structural types. Specific polycyclic hydrocarbons synthesized by this route include benzo[a]- and benzo[c]fluorene, 7H-dibenzo[c,g]-, 13H-dibenzo[a,i]-, and 13H-dibenzo[a,g]fluorene, 15H-tribenzo[a,c,i]fluorene, dibenzo[b,def]chrysene, benzo[rst]pentaphene, indeno[1,2-b]fluorene, fluoreno[3,4-c]fluorene, octahydrodibenz[a,j]anthracene, dibenz[a,j]anthracene, octahydrodibenz[a,h]anthracene, dibenz[a,h]anthracene, dibenz[a,h]anthracene, picene, benzo[c]picene, 1H-benz[bc]aceanthrylene, and 4H-cyclopenta[def]chrysene. This method with appropriate modifications appears to be potentially broader in scope than established traditional methods of polycyclic hydrocarbon synthesis.