phenanthrene-8,9-dicarboxylic acid anhydride | 25540-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: phenanthrene-8,9-dicarboxylic acid anhydride
• 英文别名: phenanthrene-1,10-dicarboxylic acid-anhydride；Phenanthren-1,10-dicarbonsaeure-anhydrid；4H,6H-Phenanthro[1,10-cd]pyran-4,6-dione；11-oxatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,8,13,15-heptaene-10,12-dione
• CAS: 25540-67-4
• 化学式: C₁₆H₈O₃
• 分子量: 248.238
• InChiKey: KDJNNXVYWZFSKX-UHFFFAOYSA-N

物化性质

• 沸点：
  502.5±19.0 °C(Predicted)
• 密度：
  1.453±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenanthrene-8,9-dicarboxylic acid anhydride 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 、 硝酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 为溶剂， -10.0~85.0 ℃ 、275.79 kPa 条件下， 反应 4.25h， 生成 8-Chloro-5-(2-dimethylamino-ethyl)-5-aza-benzo[de]anthracene-4,6-dione
  参考文献：
  名称：

  Analogues of Amonafide and Azonafide with Novel Ring Systems

  摘要：

  Three new types of amonafide and azonafide analogues were synthesized and screened in a panel of human solid tumor cells and murine L1210 leukemia cells. The structural types included tetrahydroazonafides, which have the naphthalene chromophore of amonafide within the anthracene nucleus of azonafide; phenanthrene analogues, in which the linear anthracene nucleus is replaced by the bent phenanthrene nucleus; and azaphenanthrenes. The tetrahydroazonafides were generally intermediate in potencies between amonafide and azonafide against the tumor cells, but some of them had high potencies against the L1210 cells and were more potent against the MDR strain than the sensitive strain. The phenanthrene and azaphenanthrene analogues showed no improvement on the potencies of the anthracenes.

  DOI：

  10.1021/jm9905817
• 作为产物：
  描述：

  4,5,9,10-tetrahydro-8H-acephenanthrylen-7-one 在 sodium dichromate 、 溶剂黄146 、 锌 作用下， 生成 phenanthrene-8,9-dicarboxylic acid anhydride
  参考文献：
  名称：

  CONDENSATIONS AND RING CLOSURES IN THE NAPHTHALENE SERIES. IV. A SYNTHESIS OF ACEPHENANTHRENE

  摘要：

  DOI：

  10.1021/ja01350a035

文献信息

• HEAT-SENSITIVE CHROMOGENIC COMPOSITION AND HEAT-SENSITIVE RECORDING MATERIAL FORMED USING SAID COMPOSITION
  申请人：Yamamoto Chemicals, Inc.

  公开号：EP2617578A1

  公开（公告）日：2013-07-24

  [Problem to be Solved] To provide a heat-sensitive recording material having high fastness and a vivid hue. [Solution] A heat-sensitive color-developing composition containing a hydroxyquinoline compound having a methyl group and an acid anhydride compound represented by general formula (1): wherein ring A represents a substituted or unsubstituted aromatic hydrocarbon ring, and n represents an integer of 1 to 3, and a heat-sensitive recording material containing the composition in a recording layer.

  [有待解决的问题］ 提供一种牢度高、色调鲜艳的热敏记录材料。 [解决方案］ 一种热敏显色组合物，含有一种具有甲基的羟基喹啉化合物和一种酸酐化合物，由通式（1）表示： 其中环 A 代表取代或未取代的芳香烃环，n 代表 1 至 3 的整数，以及在记录层中含有该组合物的热敏记录材料。
• Pschorr, Chemische Berichte, 1906, vol. 39, p. 3115
  作者：Pschorr

  DOI：——

  日期：——
• The synthesis and antitumor evaluation of unsymmetrical bis-imides
  作者：Robert J. Cherney、Stephen G. Swartz、Arthur D. Patten、Emeka Akamike、Jung-Hui Sun、Robert F. Kaltenbach、Steven P. Seitz、Carl H. Behrens、Zelleka Getahun、George L. Trainor、Mike Vavala、Mindy R. Kirshenbaum、Lisa M. Papp、Margaret P. Stafford、Philip M. Czerniak、Richard J. Diamond、Ronald J. McRipley、Roni J. Page、Janet L. Gross

  DOI：10.1016/s0960-894x(96)00591-4

  日期：1997.1

  Unsymmetrical bis-imides 1 were synthesized and evaluated as potential antitumor agents. These novel bis-imides were assessed using three criteria: in vitro cytotoxicity (L1210), in vitro DNA binding, and in vivo studies with human tumor xenografts in mice. These studies identified DMP 315 as a potent, water soluble antitumor agent. (C) 1997, Elsevier Science Ltd.
• BIS-IMIDE POLYCYCLIC AND HETEROCYCLIC CHROMOPHORES USEFUL AS TUMORICIDALS
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0705250A1

  公开（公告）日：1996-04-10
• HEAT-SENSITIVE COLOR-DEVELOPING COMPOSITION AND HEAT-SENSITIVE RECORDING MATERIAL COMPRISING THE COMPOSITION
  申请人：Yamaguchi Ryoji

  公开号：US20130180430A1

  公开（公告）日：2013-07-18

  [Problem to be Solved] To provide a heat-sensitive recording material having high fastness and a vivid hue. [Solution] A heat-sensitive color-developing composition containing a hydroxyquinoline compound having a methyl group and an acid anhydride compound represented by general formula (1): wherein ring A represents a substituted or unsubstituted aromatic hydrocarbon ring, and n represents an integer of 1 to 3, and a heat-sensitive recording material containing the composition in a recording layer.