1,9-bis(N,N-dimethylaminomethyl)-5-(p-tolyl)dipyrromethane | 869192-96-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,9-bis(N,N-dimethylaminomethyl)-5-(p-tolyl)dipyrromethane
• 英文别名: 1-[5-[[5-[(dimethylamino)methyl]-1H-pyrrol-2-yl]-(4-methylphenyl)methyl]-1H-pyrrol-2-yl]-N,N-dimethylmethanamine
• CAS: 869192-96-1
• 化学式: C₂₂H₃₀N₄
• 分子量: 350.507
• InChiKey: KFAUEFLULHXHPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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-(p-tolyl)dipyrromethane 、 2-(二吡咯-2-基)甲基三甲苯 在 air 、 zinc diacetate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 为溶剂， 反应 3.25h， 以18%的产率得到
  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：

  对甲基苯甲醛 在 indium(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,9-bis(N,N-dimethylaminomethyl)-5-(p-tolyl)dipyrromethane
  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

文献信息

• Methods and intermediates for the synthesis of porphyrins
  申请人：Lindsey S. Jonathan

  公开号：US20070027311A1

  公开（公告）日：2007-02-01

  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.

  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。
• 1,9-Bis(N,N-dimethylaminomethyl)dipyrromethanes in the synthesis of porphyrins bearing one or two meso substituents
  作者：Dazhong Fan、Masahiko Taniguchi、Zhen Yao、Savithri Dhanalekshmi、Jonathan S. Lindsey

  DOI：10.1016/j.tet.2005.08.028

  日期：2005.10

  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.