5,6-二氢苯并[c]蒽 | 36914-99-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 5,6-二氢苯并[c]蒽
• 英文名称: 5,6-dihydro-benz[a]anthracene
• 英文别名: 5,6-Dihydro-benz[a]anthracen；Benz(a)anthracene, 5,6-dihydro-；5,6-dihydrobenzo[a]anthracene
• CAS: 36914-99-5
• 化学式: C₁₈H₁₄
• 分子量: 230.309
• InChiKey: MKDSWPWRFOCIEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  5,6-二氢苯并[c]蒽 在 platinum(IV) oxide 、 iron(II) chloride 氢气 作用下， 以 盐酸 为溶剂， 反应 2.5h， 以85%的产率得到5,6,8,9,10,11-六氢苯并[a]蒽
  参考文献：
  名称：

  Regioselective catalytic hydrogenation of polycyclic aromatic hydrocarbons under mild conditions

  摘要：

  DOI：

  10.1021/jo01302a010
• 作为产物：
  描述：

  苯并[a]蒽 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以45%的产率得到5,6-二氢苯并[c]蒽
  参考文献：
  名称：

  Reactions of (η⁶-Arene)tricarbonylchromium Complexes: Hydrogenation, Nitration, and Bromination

  摘要：

  AbstractIn this study, we explore the reactions of coordinated arenes, e.g., hydrogenation, nitration, and bromination, to prepare compounds which are not accessible from conventional organic synthesis. The reaction products formed from reactions with the coordinated and the uncoordinated arenes are compared. The polycyclic aromatic hydrocarbons (PAHs) employed for this study include phenanthrene, methyl‐ and acetyl‐phenanthrene, and benz[a]anthracene (BA), The tricarbonylchromium group demonstrated various characteristics which influence the reactions in this work, such as an electronic effect to deactivate hydrogenation, a steric effect to exhibit, highly positional selective nitration, and a free radical mechanism to direct bromine to attack at the ring coordinated to tricarbonylchromium.

  DOI：

  10.1002/jccs.199800066

文献信息

• Cycloaromatization of α-oxoketene dithioacetals and β-oxodithioacetals with benzyl-,1-(naphthylmethyl) and 2-(naphthylmethyl)magnesium halides: Synthesis of condensed polynuclear aromatic hydrocarbons
  作者：Ch.Srinivasa Rao、Maliakel P Balu、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1016/s0040-4020(01)86411-5

  日期：1991.1

  An efficient route for the synthesis of substituted naphthalenes, phenanthrenes and other polynuclear aromatic hydrocarbons has been developed. The methodology involves 1,2- (or sequential 1,4- and 1,2-) addition of either benzyl, 1-(naphthylmethyl) or 2-(naphthylmethyl) magnesium halides to α-oxoketene dithioacetals or β-oxodithioacetals followed by borontrifluoride etherate catalyzed cycloaromatization

  已经开发了合成取代的萘，菲和其他多核芳烃的有效途径。该方法包括在α-氧杂环丁烯二硫缩醛或β-氧二硫缩醛中加入苄基，1-（萘基甲基）或2-（萘基甲基）卤化镁的1,2-（或顺序的1,4-和1,2-），然后再加入三氟化硼醚化物催化所得甲醇的环芳构化。
• Vejdelek; Kakac, Collection of Czechoslovak Chemical Communications, 1955, vol. 20, p. 571,575
  作者：Vejdelek、Kakac

  DOI：——

  日期：——
• Regioselective catalytic hydrogenation of polycyclic aromatic hydrocarbons under mild conditions
  作者：Peter P. Fu、Hong M. Lee、Ronald G. Harvey

  DOI：10.1021/jo01302a010

  日期：1980.7
• Reactions of (η⁶-Arene)tricarbonylchromium Complexes: Hydrogenation, Nitration, and Bromination
  作者：Z. Y. Own

  DOI：10.1002/jccs.199800066

  日期：1998.6

  AbstractIn this study, we explore the reactions of coordinated arenes, e.g., hydrogenation, nitration, and bromination, to prepare compounds which are not accessible from conventional organic synthesis. The reaction products formed from reactions with the coordinated and the uncoordinated arenes are compared. The polycyclic aromatic hydrocarbons (PAHs) employed for this study include phenanthrene, methyl‐ and acetyl‐phenanthrene, and benz[a]anthracene (BA), The tricarbonylchromium group demonstrated various characteristics which influence the reactions in this work, such as an electronic effect to deactivate hydrogenation, a steric effect to exhibit, highly positional selective nitration, and a free radical mechanism to direct bromine to attack at the ring coordinated to tricarbonylchromium.