(P)-1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylic acid chloride

• 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: (P)-1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylic acid chloride
• 英文别名: (P)-1,12-dimethylbenzophenanthrene-5,8-dicarboxylic acid dichloride；(P)-1,12-dimethylbenzo[c]phenanthrene-5,8-dicarbonyl dichloride；1,12-Dimethylbenzo[c]phenanthrene-5,8-dicarbonyl chloride；1,12-dimethylbenzo[c]phenanthrene-5,8-dicarbonyl chloride
• 化学式: C₂₂H₁₄Cl₂O₂
• 分子量: 381.258
• InChiKey: PANGWUXDUPVJCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  (P)-1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylic acid chloride 在 氯化亚砜 、 硫酸 、 氨 、 硝酸 作用下， 以 甲苯 为溶剂， 反应 15.5h， 生成 1,12-Dimethyl-2,11-dinitro-benzo[c]phenanthrene-5,8-dicarbonitrile
  参考文献：
  名称：

  对称聚硝基螺旋烯的合成及其在电荷转移络合中的手性识别。

  摘要：

  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。

  DOI：

  10.1021/jo001419a
• 作为产物：
  描述：

  (P)-1-(4-benzyloxycarbonylamino-3,5-dimethylphenyl)-1-{4-(8-carboxy-1,12-dimethylbenzo[c]phenanthrene-5-carbonylamino)-3,5-dimethylphenyl}cyclohexane 在 氯化亚砜 作用下， 反应 7.0h， 以72%的产率得到(P)-1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylic acid chloride
  参考文献：
  名称：

  A Building Block Method for the Synthesis of Higher Cycloamides

  摘要：

  Series of cyclic amides containing optically active helicene, (P)-1, 12-dimethylbenzo[c]phenanthrene, are synthesized using a building block method. The building block consists of one (P)-helicene unit and one dianiline unit with its amino-terminal-protected with benzyloxycarbonyl and its acid terminal activated as acid chloride. The coupling with (P,P....)-[(n - 3) + (n - 2)]diamine followed by deprotection gives (P,P....)-[(n - 1) + n]diamine, which possesses n - 1 parts of (P)-helicene and n parts of dianiline. Cyclization of the (PP....)-[(n - 1) + n]diamine with helicenediacid dichloride gives (P,P....)-[n + n]cycloamide. All the members of (P,P)-[2 + 2]cycloamide to (P,P,P,P,P,P,P,P,P,P)-[10 + 10]cycloamide are synthesized using this method, and are compared spectroscopically.

  DOI：

  10.1021/jo0013047

文献信息

• Synthesis and monolayer behaviors of optically active 1,12- dimethylbenzo[c]phenanthrene-5,8-diamides and the formation of chiral langmuir-blodgett films
  作者：Hitoshi Okubo、Fei Feng、Daisuke Nakano、Tomokazu Hirata、Masahiko Yamaguchi、Tokuji Miyashita

  DOI：10.1016/s0040-4020(99)00969-2

  日期：1999.12

  previously reported that an optically active cyclic amide consisting of a helical chiral 1,12-dimethylbenzo[c]phenanthrene-5, 8-dicarboxylic acid forms a stable monolayer on the water surface, and that the monolayer can be transferred on a solid support giving optically active Langmuir-Blodgett (LB) films. In this study, several related amides were synthesized, and their monolayer behaviors were investigated

  我们以前曾报道过，由螺旋手性1,12-二甲基苯并[ c ]菲-5，8-二羧酸组成的旋光环状酰胺在水表面形成稳定的单层，并且该单层可以转移到固体载体上得到光学活性的朗缪尔-布洛杰特（LB）膜。在这项研究中，合成了几种相关的酰胺，并对其单层行为进行了研究，以期制备具有官能团的光学活性LB膜。结果表明，环状酰胺结构和环己基部分对于在水表面形成稳定的单分子层至关重要。仲酰胺的N-烷基化不会严重影响单层的形成，而手性LB膜可通过N，N获得环酰胺的-双（3-巯基丙基）衍生物。
• Ferroelectric Alkylamide-Substituted Helicene Derivative with Two-Dimensional Hydrogen-Bonding Lamellar Phase
  作者：Hayato Anetai、Takashi Takeda、Norihisa Hoshino、Higashi Kobayashi、Nozomi Saito、Masanori Shigeno、Masahiko Yamaguchi、Tomoyuki Akutagawa

  DOI：10.1021/jacs.8b11222

  日期：2019.2.13

  liquid crystallinity for the optically active derivative because of the different molecular assembly structure. The racemic phase is constructed through a two-dimensional (2D) N-H···O═ hydrogen-bonding network, which shows ferroelectric P- E hysteresis curves at above 340 K. The collective dipole inversion in the 2D layer contributes to the ferroelectricity in the lamellar phase. The remanent polarization

  烷基酰胺（-CONHC nH2 n+1）-取代苯及其芘衍生物通过一维（1D）分子间NH…O=氢键相互作用显示出盘状六方柱状液晶相，其方向通过施加交流电压反转。极性氢键链和偶极子反转揭示了铁电极极化电场 (P-E) 滞后曲线。带有两个 -CONHC14H29 链的非 π 平面螺旋衍生物也表明铁电响应。外消旋螺旋烯衍生物在330-420 K的温度范围内显示出双层层状液晶相，而旋光衍生物由于不同的分子组装结构而没有液晶性。外消旋相是通过二维 (2D) NH…O= 氢键网络构建的，在 340 K 以上显示铁电 P-E 滞后曲线。 2D 层中的集体偶极反转有助于铁电性层状相。11.1 μC cm-2 的剩余极化 (Pr) 是 π 平面苯和芘基 1D 铁电体的 6 倍。二维系统中氢键位点的密度和畴取向均高于一维柱状系统。1 μC cm-2 比基于 π 平面苯和芘的一维铁电体高约 6 倍。二维系统中氢键
• 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。
• 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.
• Cyclic Anhydrides Formed from 1,12-Dimethylbenzo[c]phenanthrene-5,8-dicarboxylic Acid and1,3-Benzene-dicarboxylic Acids
  作者：Masahiko Yamaguchi、Hitoshi Okubo

  DOI：10.3987/com-99-s97

  日期：——