15H-Tribenzofluorene | 201-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 15H-Tribenzofluorene
• 英文别名: 15H-benz[4,5]indeno[1,2-l]phenanthrene；15H-Benz[4,5]indeno[1,2-l]phenanthren；Hexacyclo[12.11.0.02,7.08,13.015,24.018,23]pentacosa-1(14),2,4,6,8,10,12,15(24),16,18,20,22-dodecaene
• CAS: 201-50-3
• 化学式: C₂₅H₁₆
• 分子量: 316.402
• InChiKey: AHLKTUXBHDFQGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  15H-Tribenzofluorene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 溶剂黄146 为溶剂， 以86%的产率得到15H-Tribenzofluorenone
  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：

  15H-Tribenzofluorenone 在 肼 作用下， 生成 15H-Tribenzofluorene
  参考文献：
  名称：

  Martin; Vassart, Bulletin des Societes Chimiques Belges, 1951, vol. 60, p. 325,330

  摘要：

  DOI：

文献信息

• An Efficient Synthesis of Benzofluorenes Via α-Alkoxycarbonyldiarylmethyl Cations
  作者：A. C. Hopkinson、E. Lee-Ruff、M. Maleki

  DOI：10.1055/s-1986-31637

  日期：——

  Rearrangements of α-alkoxycarbonyldiarylmethyl cations lead to 9-fluorenecarboxylic esters. Decarboxylation of these esters generates the fluorene derivatives 9a-f. The precursors to the cations are the α-hydroxyesters 6a-g.This conversion constitutes a facile synthesis of benzofluorenes.

  α-烷氧基羧基二芳基甲基阳离子的重排导致9-芴酸酯的生成。这些酯的脱羧反应生成氟烯衍生物9a-f。这些阳离子的前驱体是α-羟基酯6a-g。这一转化构成了苯并芴类化合物的简便合成。
• The Cyclization of Di- and Triaryl Carbinols. I. Contribution to the Mechanism of Cyclization Reactions
  作者：Felix Bergmann、Shalom Israelashwili

  DOI：10.1021/ja01205a001

  日期：1946.1
• 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：——
• HOPKINSON A. C.; LEE-RUFF E.; MALEKI M., SYNTHESIS,(1986) N 5, 366-371
  作者：HOPKINSON A. C.、 LEE-RUFF E.、 MALEKI M.

  DOI：——

  日期：——
• 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.