萘并萘-5,12-二甲醛 | 71440-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 中文名称: 萘并萘-5,12-二甲醛
• 英文名称: 5,12-diformylnaphthacene
• 英文别名: 5,12-diformyltetracene；5,12-benz[b]anthracene dicarboxaldehyde；Benzoanthracendicarbaldehyd-5,12；Benzo[b]anthracendicarbaldehyd-5,12；Tetracene-5,12-dicarbaldehyde
• CAS: 71440-79-4
• 化学式: C₂₀H₁₂O₂
• 分子量: 284.314
• InChiKey: RXDJVBXMOZKSHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  萘并萘-5,12-二甲醛 在 吡啶 、 盐酸羟胺 、 乙酸酐 作用下， 反应 6.5h， 生成 5,12-dicyanonaphthacene
  参考文献：
  名称：

  Synthesis, Properties, and Ambipolar Organic Field-Effect Transistor Performances of Symmetrically Cyanated Pentacene and Naphthacene as Air-Stable Acene Derivatives

  摘要：

  5,12-Dicyanonaphthacene and 6,13-dicyanopentacene have been synthesized for the first time. The LUMO and HOMO levels are deepened as predicted and fabricated organic field-effect transistors (OFETs) showed ambipolar responses with carrier mobilities of 10(-3) cm(2)/V.s.

  DOI：

  10.1021/ol200145r
• 作为产物：
  描述：

  并四苯 在 lead(IV) acetate 、 氢氧化钾 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 萘并萘-5,12-二甲醛
  参考文献：
  名称：

  Antitumor agents. II. Bis(guanylhydrazones) of anthracene-9,10-dicarboxaldehydes

  摘要：

  9,10-Anthracenedicarboxaldehyde bis[(4,5-dihydro-1H-imidazol-2-yl)hydrazone] (bisantrene, VI-1) showed anticancer activity in mice vs. both leukemias and solid tumors. Increases in life span vs. the following neoplasms were: P-388 leukemia, 137%; B-16 melanoma, 122%; Lieberman plasma cell tumor, greater than 85%; colon tumor 26, 150%; Ridgway osteogenic sarcoma, 85%. There were significant numbers of long-term survivors. Both DNA and RNA synthesis were strongly inhibited. The drug was resistant to biodegradation and was bound strongly to tissues; in monkeys the half-life for disappearance from serum was 6 days. Related hydrazones were synthesized, and structure-activity relationships are discussed. Two routes to ring-substituted anthracene-9,10-dicarboxaldehyde intermediates were developed.

  DOI：

  10.1021/jm00347a006

文献信息

• Synthesis of pentacene-, tetracene- and anthracene bisimides using double-cyclization reaction mediated by bismuth(iii) triflate
  作者：Shuhei Katsuta、Kazuki Tanaka、Yukihiro Maruya、Shigeki Mori、Sadahiro Masuo、Tetsuo Okujima、Hidemitsu Uno、Ken-ichi Nakayama、Hiroko Yamada

  DOI：10.1039/c1cc13980k

  日期：——

  Novel bisimide-fused acenes were synthesized via bismuth triflate mediated double-cyclization reaction of acid chlorides and isocyanates. Their optical and electrical properties revealed significantly smaller HOMO-LUMO gaps compared with those of their parent acenes. Fabricated OFET based on tetracene bisimide showed n-type OFET outputs.

  通过三氟甲磺酸铋介导的酰氯和异氰酸酯的双环化反应合成了新型的双酰亚胺融合的并苯。它们的光学和电学性质显示出比其母本苯并乙炔的HOMO-LUMO间隙小得多。基于并四苯双酰亚胺制造的OFET显示出n型OFET输出。
• Novel dihydrobenzanthracene derivatives
  申请人：American Cyanamid Company

  公开号：US04187373A1

  公开（公告）日：1980-02-05

  This disclosure describes benzanthracene-5,12(or 7,12)-dicarboxaldehyde-bis-hydrazones and the 5,12(or 7,12)-dihydrobenzanthracene-5,12(or 7,12)-dicarboxaldehyde-bis-hydrazones useful as antibacterial agents, for inhibiting the growth of transplanted mouse tumors, and for inducing the regression and/or pallation of leukemia and related cancers.

  本公开描述了苯并蒽-5,12（或7,12）-二甲酰肼双肼和5,12（或7,12）-二氢苯并蒽-5,12（或7,12）-二甲酰肼双肼，它们可用作抗菌剂，用于抑制移植小鼠肿瘤的生长，并诱导白血病和相关癌症的退缩和/或缓解。
• FR2446285
  申请人：——

  公开号：——

  公开（公告）日：——
• US4187373A
  申请人：——

  公开号：US4187373A

  公开（公告）日：1980-02-05
• Antitumor agents. II. Bis(guanylhydrazones) of anthracene-9,10-dicarboxaldehydes
  作者：K. C. Murdock、R. G. Child、Yang I Lin、J. D. Warren、P. F. Fabio、Ving J. Lee、P. T. Izzo、S. A. Lang、Robert B. Angier

  DOI：10.1021/jm00347a006

  日期：1982.5

  9,10-Anthracenedicarboxaldehyde bis[(4,5-dihydro-1H-imidazol-2-yl)hydrazone] (bisantrene, VI-1) showed anticancer activity in mice vs. both leukemias and solid tumors. Increases in life span vs. the following neoplasms were: P-388 leukemia, 137%; B-16 melanoma, 122%; Lieberman plasma cell tumor, greater than 85%; colon tumor 26, 150%; Ridgway osteogenic sarcoma, 85%. There were significant numbers of long-term survivors. Both DNA and RNA synthesis were strongly inhibited. The drug was resistant to biodegradation and was bound strongly to tissues; in monkeys the half-life for disappearance from serum was 6 days. Related hydrazones were synthesized, and structure-activity relationships are discussed. Two routes to ring-substituted anthracene-9,10-dicarboxaldehyde intermediates were developed.