13,14-Dimethyldibenzo[b,j][4,7]phenanthrolin | 98628-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 13,14-Dimethyldibenzo[b,j][4,7]phenanthrolin
• 英文别名: 13,14-dimethylquinolino[3,2-a]acridine
• CAS: 98628-28-5
• 化学式: C₂₂H₁₆N₂
• 分子量: 308.382
• InChiKey: IMMBVQODZRGDPC-UHFFFAOYSA-N

物化性质

• 熔点：
  211.5-213.0 °C(Solv: ethanol (64-17-5))
• 沸点：
  563.2±23.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  13,14-Dimethyldibenzo[b,j][4,7]phenanthrolin 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 13,14-dimethyl-6,7 dihydrodibenzo[b,j][4,7]phenanthroline
  参考文献：
  名称：

  Optically active aromatics possessing helical chirality: one-pot synthesis, optical resolution and crystal structure of 13,14-dimethyldibenzo[b, j ][4,7]phenanthroline and its dihydro form as a novel chiral building block

  摘要：

  通过一步反应合成了螺旋芳烃13,14-二甲基二苯并[b,j][4,7]菲啰啉1及其二氢形式2，通过HPLC分离出各自的对应体，并确定了它们的单晶结构。

  DOI：

  10.1039/a805076g
• 作为产物：
  描述：

  N,N'-二苯基-1,4-苯二胺 在 sodium acetate 、 zinc(II) chloride 作用下， 生成 13,14-Dimethyldibenzo[b,j][4,7]phenanthrolin
  参考文献：
  名称：

  One-Pot Synthesis of Helical Aromatics:  Stereoselectivity, Stability against Racemization, and Assignment of Absolute Configuration Assisted by Experimental and Theoretical Circular Dichroism

  摘要：

  Helical aromatics (1) were synthesized via one step in good quantity by solvent-free condensation of NY-p-phenylenediamine (2) and various carboxylic acids in the presence of a Lewis acid. Microwave irradiation greatly facilitated the condensation reaction to furnish 1 with a 100% diastereo- and a 50% enantioselectivity, when a chiral carboxylic acid was utilized. If, derived from 2-methylglutaric acid, was quite stable, no racemization taking place even at 200 degreesC. The assignment of the absolute configurations to the helical aromatics has been achieved by experimental and theoretical CD spectra calculated by time-dependent density functional theory.

  DOI：

  10.1021/jo048858k

文献信息

• Optically active aromatics possessing helical chirality: one-pot synthesis, optical resolution and crystal structure of 13,14-dimethyldibenzo[b, j ][4,7]phenanthroline and its dihydro form as a novel chiral building block
  作者：Yasutaka Tanaka、Akemi Sekita、Hiroshi Suzuki、Mitsuji Yamashita、Tatsuo Oshikawa、Tadashi Yonemitsu、Akiyoshi Torii

  DOI：10.1039/a805076g

  日期：——

  Helical aromatics, 13,14-dimethyldibenzo[b,j][4,7]phenanthroline 1 and its dihydro form 2 were synthesized via a one-step reaction, resolved into each of the enantiomers by HPLC and their single crystal structures were determined.

  通过一步反应合成了螺旋芳烃13,14-二甲基二苯并[b,j][4,7]菲啰啉1及其二氢形式2，通过HPLC分离出各自的对应体，并确定了它们的单晶结构。
• Aromatic condensation compounds useful as opticaly active building blocks
  申请人：Japan Science and Technology Corporation

  公开号：EP0861840A1

  公开（公告）日：1998-09-02

  Disclosed are aromatic condensation compounds useful as building blocks for construction of various types of optically active substances and reagent, wherein the aromatic condensation compounds are represented by general formula (1) below and capable of forming enantiomeric isomers. In the formula, two Rs are the same or different functional groups and selected from among linear, branched and cyclic hydrocarbon groups of 1-16 carbon atoms, either of which R may be hydrogen. A portion of the aromatic nucleus may be reduced, or at least one of the two nitrogen atoms may be quaternary. The aromatic condensation compounds can be produced by heating and reacting N,N'-diphenyl-p-phenylenediamine with a carboxylic acid represented by the general formula-RCOOH in an amount of at least 2 molar equivalents with respect to the diamine, at 180-210°C in the presence of a Lewis acid such as zinc chloride.

  本发明公开了芳香族缩合化合物，可作为构建各类光学活性物质和试剂的构件，其中芳香族缩合化合物由以下通式（1）表示，并能形成对映异构体。式中，两个 R 是相同或不同的官能团，选自 1-16 个碳原子的线性、支链和环状烃基，其中任一 R 可以是氢。芳香族核的一部分可以被还原，或者两个氮原子中至少有一个可以是四价氮原子。在路易斯酸（如氯化锌）存在下，将 N,N'-二苯基对苯二胺与通式-RCOOH 所代表的羧酸在 180-210°C 下加热反应，反应物的摩尔当量至少为二元胺的 2 摩尔当量，即可制得芳香族缩合化合物。
• Hellwinkel, Dieter; Ittemann, Peter, Liebigs Annalen der Chemie, 1985, # 7, p. 1501 - 1507
  作者：Hellwinkel, Dieter、Ittemann, Peter

  DOI：——

  日期：——
• HELLWINKEL, D.;ITTEMANN, P., LIEBIGS ANN. CHEM., 1985, N 7, 1501-1507
  作者：HELLWINKEL, D.、ITTEMANN, P.

  DOI：——

  日期：——
• JPH10245382A
  申请人：——

  公开号：JPH10245382A

  公开（公告）日：1998-09-14