1,9-bis(N,N-dimethylaminomethyl)-5-phenyldipyrromethane | 869192-92-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,9-bis(N,N-dimethylaminomethyl)-5-phenyldipyrromethane
• 英文别名: 1-[5-[[5-[(dimethylamino)methyl]-1H-pyrrol-2-yl]-phenylmethyl]-1H-pyrrol-2-yl]-N,N-dimethylmethanamine
• CAS: 869192-92-7
• 化学式: C₂₁H₂₈N₄
• 分子量: 336.48
• InChiKey: HSRZAPIUPLQPQW-UHFFFAOYSA-N

物化性质

• 熔点：
  76-78 °C
• 沸点：
  465.6±40.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,9-bis(N,N-dimethylaminomethyl)-5-phenyldipyrromethane 在 air 、 zinc diacetate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 19.25h， 生成 zinc(II)-5-(4-methylphenyl)-15-phenylporphyrin
  参考文献：
  名称：

  1,9-Bis(N,N-dimethylaminomethyl)dipyrromethanes in the synthesis of porphyrins bearing one or two meso substituents

  摘要：

  A synthesis of 5,15-disubstituted zinc-porphyrins has been developed that employs condensation of a 1,9-bis(N,N-dimethylaminomethyl)dipyrromethane+a dipyrromethane in refluxing ethanol containing zinc acetate followed by oxidation with DDQ. The NN-dimethylaminomethylation of the dipyrromethane was achieved via Eschenmoser's reagent (N,N-dimethylmethyleneammonium iodide) in CH2Cl2 at room temperature. The synthesis is compatible with diverse substituents (e.g., alkyl, aryl, ester, acetal) and enables rapid synthesis of trans-AB-, A(2)-, and A-porphyrins. The synthesis of > 40 zinc porphyrins has been surveyed; 13 zinc porphyrins were isolated in yields of 5-20% without detectable scrambling. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.028
• 作为产物：
  描述：

  1,9-bis(N,N-dimethylaminomethyl)-5-phenyldipyrromethane hydroiodide 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 1,9-bis(N,N-dimethylaminomethyl)-5-phenyldipyrromethane
  参考文献：
  名称：

  Methods and intermediates for the synthesis of porphyrins

  摘要：

  通过以下步骤进行制备卟啉的方法：(a) 缩合(i) 公式II中的1,9-双(N,N-)二烷氨甲基二吡咯甲烷与(ii) 二吡咯甲烷以产生反应产物；然后(b) 氧化反应产物；然后(c) 可选择性地去金属化所述反应产物以产生卟啉。该反应特别适用于制备在A和/或B(第5和/或15)位置具有广泛取代基的取代卟啉。

  公开号：

  US20070027311A1

文献信息

• Effects of <i>meso</i>-diarylamino group of porphyrins on optical and electrochemical properties
  作者：Tomohiro Higashino、Yamato Fujimori、Issei Nishimura、Hiroshi Imahori

  DOI：10.1142/s1088424619500652

  日期：2020.1

  Introduction of an electron-donating meso-diarylamino group into a porphyrin core affords its broadened and red-shifted absorption and raises the HOMO level of the porphyrin. In this regard, porphyrins with multiple meso-diarylamino groups are expected to show unique optical and electrochemcial properties depending on the number of the meso-diarylamino groups. Herein, we report a series of porphyrins with a different number of the meso-diarylamino groups. They were prepared by the iodine(III)-mediated oxidative amination reaction of the corresponding meso-free porphyrins. With increasing the number of the meso-diarylamino groups, both red shifts and broadening in the absorption and negative shifts in the oxidation potential were observed. Notably, the oxidation potential of the porphyrin with four meso-diarylamino groups is comparable to that of tetrathiafulvalene, which is one of representative electron donors, suggesting the potential utility of multiply meso-aminated porphyrins as hole-transporting materials and as electron donors forming charge-transfer complexes with electron acceptors. We believe that this study sheds light on porphyrins with multiple electron-donating groups as organic functional materials.

  在卟啉核心中引入一个供电子的介二叉氨基，可使卟啉的吸收变宽、变红，并提高卟啉的 HOMO 水平。因此，具有多个间位二芳基氨基的卟啉有望根据间位二芳基氨基的数量显示出独特的光学和电化学性质。在此，我们报告了一系列具有不同数量介观二芳基氨基的卟啉。这些卟啉是通过碘（III）介导的相应无间氨基卟啉的氧化胺化反应制备的。随着介基-二芳基氨基基团数量的增加，可观察到吸收的红移和展宽以及氧化电位的负移。值得注意的是，含有四个间位二酰胺基团的卟啉的氧化电位与具有代表性的电子供体之一的四硫富勒烯的氧化电位相当，这表明多重间位酰胺卟啉作为空穴传输材料和电子供体与电子受体形成电荷转移复合物的潜在用途。我们认为这项研究揭示了具有多个电子供体基团的卟啉作为有机功能材料的前景。
• METHODS AND INTERMEDIATES FOR THE SYNTHESIS OF PORPHYRINS
  申请人：Lindsey Jonathan S.

  公开号：US20090198049A1

  公开（公告）日：2009-08-06

  A method of making a porphyrin is carried out by: (a) condensing (i) a 1,9-bis(N,N-)dialkylaminomethyl)dipyrromethane of Formula II: with (ii) a dipyrromethane to produce a reaction product; then (b) oxidizing the reaction product; and then (c) optionally demetallating said reaction product to produce the porphyrin. The reaction is particularly useful for making substituted porphyrins with a wide range of substituents at the A and/or B (the 5 and/or 15) positions.
• US7501508B2
  申请人：——

  公开号：US7501508B2

  公开（公告）日：2009-03-10
• US7951939B2
  申请人：——

  公开号：US7951939B2

  公开（公告）日：2011-05-31
• US8212023B2
  申请人：——

  公开号：US8212023B2

  公开（公告）日：2012-07-03