(+/-)-1,12-dimethylbenzophenanthrene-5,8-dinitrile | 219585-81-6

• 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: (+/-)-1,12-dimethylbenzophenanthrene-5,8-dinitrile
• 英文别名: (+/-)-1,12-dimethylbenzo[c]phenanthrene-5,8-dicarbonitrile；1,12-Dimethylbenzo[c]phenanthrene-5,8-dicarbonitrile
• CAS: 219585-81-6
• 化学式: C₂₂H₁₄N₂
• 分子量: 306.367
• InChiKey: FYGKAZRLMNPXKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-1,12-dimethylbenzophenanthrene-5,8-dinitrile 在 sodium hydroxide 、 氯化亚砜 作用下， 以 乙二醇 为溶剂， 反应 25.0h， 生成 (P)-1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylic acid dichloride
  参考文献：
  名称：

  Macrocyclic Amides Consisting of Helical Chiral 1,12-Dimethylbenzo[c]phenanthrene-5,8-dicarboxylate

  摘要：

  Helical chiral 1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylic acid was synthesized and resolved in multigram quantities. The absolute configuration was determined by X-ray analysis of the bis(camphorsultamamide) derivative. A series of optically active macrocyclic amides consisting of the chiral unit and a dianiline spacer were synthesized by one-pot procedures, and their structures were compared by spectroscopy and X-ray crystallography. One of the cycloamides exhibited catalytic activity in the asymmetric addition of diethylzinc to aromatic aldehydes. N-Alkylated derivatives were also synthesized, which possessed folded structures distinct from those of the parent cyclic amides.

  DOI：

  10.1021/jo981720f
• 作为产物：
  描述：

  cis-1,12-Dimethyl-5,6,6a,7,8,12b-hexahydrobenzophenanthrene-5,8-dione 在 吡啶 、 zinc(II) iodide 、 三氯氧磷 作用下， 以 苯 为溶剂， 反应 44.0h， 生成 (+/-)-1,12-dimethylbenzophenanthrene-5,8-dinitrile
  参考文献：
  名称：

  Synthesis of optically active macrocycles consisting of helical chiral unit 1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylate as a novel chiral building block

  摘要：

  以克为单位制备出光学纯度为 1,12-二甲基苯并[c]菲-5,8-二羧酸 1，并合成了一系列由螺旋手性单元组成的大环。

  DOI：

  10.1039/cc9960001771

文献信息

• Synthesis of Symmetrical Polynitrohelicenes and Their Chiral Recognition in the Charge Transfer Complexation
  作者：Hitoshi Okubo、Daisuke Nakano、Shuzo Anzai、Masahiko Yamaguchi

  DOI：10.1021/jo001419a

  日期：2001.1.1

  former compound is converted to a 2,4,9,11-tetranitrohelicene. The tetranitrohelicenes form charge-transfer (CT) complexes with an electron-rich chiral diaminohelicene in solution. The studies on the chiral recognition reveal that the combinations of the same configuration of the helicenes form more stable complexes than that of the enantiomeric helicenes.

  光学活性的1,12-二甲基苯并[c]菲-5,8-二羧酸的衍生物可以被区域选择性地硝化，从而得到对称的多官能团螺旋烯。用发烟硝酸在乙酸的4,9位上将二羧酸或其二甲酯酯化。当反应在发烟硝酸中进行时，得到2,4,9,11-四硝基nitro烯。类似地，根据条件，1,12-二甲基苯并[c]菲-5,8-二腈得到2,11-二硝基或4,9-二硝基nitro烯，前一种化合物被转化为2,4,9,11 -四硝基hel烯。四硝基螺旋酮与溶液中的富电子手性二氨基螺旋烯形成电荷转移（CT）络合物。
• Synthesis and Charge Transfer Complexation of Chiral Polynitrohelicenes
  作者：Hitoshi Okubo、Daisuke Nakano、Masahiko Yamaguchi、Chizuko Kabuto

  DOI：10.1246/cl.2000.1316

  日期：2000.11

  12-Dimethylbenzo[c]phenanthrene-5,8-dinitrile is nitrated at symmetrical positions giving 2,11-dinitro-, 4,9-dinitro, and 2,4,9,11-tetranitrohelicenes depending on the reaction conditions. The electron-deficient helicenes form charge-transfer (CT) complexes with pyrene in the solution as well as in the solid state. Crystal of the CT complex obtained from either (P)- or (±)-tetranitrohelicene possesses

  1,12-二甲基苯并[c]菲-5,8-二腈在对称位置硝化，根据反应条件得到2,11-二硝基-、4,9-二硝基和2,4,9,11-四硝基螺旋。缺电子螺旋在溶液和固态中与芘形成电荷转移 (CT) 络合物。从(P)-或(±)-四硝基螺旋烯获得的CT复合物晶体具有柱状结构，但具有不同的螺旋度、直径和螺距。
• Folding of dihelicenetriamines in water
  作者：Shinobu Honzawa、Hitoshi Okubo、Keiichi Nakamura、Shuzo Anzai、Masahiko Yamaguchi、Chizuko Kabuto

  DOI：10.1016/s0957-4166(02)00249-5

  日期：2002.6

  Diastereomeric triamines containing two helicene moieties, 1,12-dimethylbenzo[c]phenanthrene, were synthesized and found to form folded structures in the water. Such folding was not observed for an achiral compound possessing a naphthalene moiety. The (M,M)-dihelicenetriamine with matching configuration at the helicene moieties formed a more stable folded structure than the (P,M)-isomer containing two enantiomeric helicene groups. The most stable folded conformation was predicted by the Monte Carlo method with Amber force field of the dihelicenetriamine. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Macrocyclic Amides Consisting of Helical Chiral 1,12-Dimethylbenzo[<i>c</i>]phenanthrene-5,8-dicarboxylate
  作者：Hitoshi Okubo、Masahiko Yamaguchi、Chizuko Kabuto

  DOI：10.1021/jo981720f

  日期：1998.12.1

  Helical chiral 1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylic acid was synthesized and resolved in multigram quantities. The absolute configuration was determined by X-ray analysis of the bis(camphorsultamamide) derivative. A series of optically active macrocyclic amides consisting of the chiral unit and a dianiline spacer were synthesized by one-pot procedures, and their structures were compared by spectroscopy and X-ray crystallography. One of the cycloamides exhibited catalytic activity in the asymmetric addition of diethylzinc to aromatic aldehydes. N-Alkylated derivatives were also synthesized, which possessed folded structures distinct from those of the parent cyclic amides.
• Synthesis of optically active macrocycles consisting of helical chiral unit 1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylate as a novel chiral building block
  作者：Masahiko Yamaguchi、Hitoshi Okubo、Masahiro Hirama

  DOI：10.1039/cc9960001771

  日期：——

  Optically pure 1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylic acid 1 is prepared in gram quantities, and a series of macrocycles consisting of the helical chiral unit are synthesized.

  以克为单位制备出光学纯度为 1,12-二甲基苯并[c]菲-5,8-二羧酸 1，并合成了一系列由螺旋手性单元组成的大环。