dimethyl 14-benzyl-6,6,7,7-tetramethyl-3,4,6,7,10,11-hexahydro-2H,9H,14H-[1,4,8,11]tetraoxacyclotetradecino[2,3-c]pyrrole-13,15-dicarboxylate | 376395-22-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 14-benzyl-6,6,7,7-tetramethyl-3,4,6,7,10,11-hexahydro-2H,9H,14H-[1,4,8,11]tetraoxacyclotetradecino[2,3-c]pyrrole-13,15-dicarboxylate
• 英文别名: Dimethyl 16-benzyl-7,7,8,8-tetramethyl-2,6,9,13-tetraoxa-16-azabicyclo[12.3.0]heptadeca-1(17),14-diene-15,17-dicarboxylate
• CAS: 376395-22-1
• 化学式: C₂₇H₃₇NO₈
• 分子量: 503.593
• InChiKey: YNMFYQUJNNKCME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  94.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl 14-benzyl-6,6,7,7-tetramethyl-3,4,6,7,10,11-hexahydro-2H,9H,14H-[1,4,8,11]tetraoxacyclotetradecino[2,3-c]pyrrole-13,15-dicarboxylate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 54.0h， 生成 6,6,7,7-tetramethyl-3,4,6,7,10,11-hexahydro-2H,9H,14H-[1,4,8,11]tetraoxacyclotetradecino[2,3-c]pyrrole-13,15-dicarboxylic acid
  参考文献：
  名称：

  3,4-Alkylenedioxypyrroles:  Functionalized Derivatives as Monomers for New Electron-Rich Conducting and Electroactive Polymers

  摘要：

  New functionalized derivatives of 3,4-ethylenedioxypyrrole (EDOP, 5a) and 3,4-(1,3-propylenedioxy)-pyrrole (ProDOP, 5b) as especially electron-rich monomers which yield highly electroactive and stable conducting polymers useful for a diverse set Of applications have been synthesized. N-Alkylations of ProDOP were carried out to yield a variety of ProDOP derivatives having alkyl, sulfonatoalkoxy, glyme, and glyme alcohol pendant chains. Iodization of EDOP and ProDOP via iodo-decarboxylation afforded iodo-functionalized derivatives useful for subsequent aryl coupling chemistry. N-Protection and formylation of EDOP, followed by Knoevenagel condensation of the resultant 2-formyl-EDOP with aryl acetonitrile derivatives, led to 1-cyano-2-(2-(3,4-ethylenedioxy-pyrryl))-1-(2-thienyl)vinylene (23) (Th-CNV-EDOP) and 1-cyano-2-(2-(3,4-ethylenedioxypyrryl))-1-(2-(3,4-ethylenedioxythienyl)vinylene (26) (EDOT-CNV-EDOP). A 14-crown-4-ether 34 based dioxypyrrole was synthesized with a cavity potentially useful for lithium ion coordination and sensing in the resultant electroactive polymer. C-Alkylated ProDOPs (43a, 43b, and 43c) containing octyl, ethylhexyl, and dioctyl substituents appended to the central methylene of the propylene bridge, were prepared as monomers for potentially soluble pi -conjugated polymers.

  DOI：

  10.1021/jo001620l
• 作为产物：
  描述：

  二甲基1-苄基-3,4-二羟基-1H-吡咯-2,5-二羧酸酯 、 4,7-dioxa-5,5,6,6-tetramethyldecane-1,10-diol bis(p-toluenesulfonate) 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.0h， 以45%的产率得到dimethyl 14-benzyl-6,6,7,7-tetramethyl-3,4,6,7,10,11-hexahydro-2H,9H,14H-[1,4,8,11]tetraoxacyclotetradecino[2,3-c]pyrrole-13,15-dicarboxylate
  参考文献：
  名称：

  3,4-Alkylenedioxypyrroles:  Functionalized Derivatives as Monomers for New Electron-Rich Conducting and Electroactive Polymers

  摘要：

  New functionalized derivatives of 3,4-ethylenedioxypyrrole (EDOP, 5a) and 3,4-(1,3-propylenedioxy)-pyrrole (ProDOP, 5b) as especially electron-rich monomers which yield highly electroactive and stable conducting polymers useful for a diverse set Of applications have been synthesized. N-Alkylations of ProDOP were carried out to yield a variety of ProDOP derivatives having alkyl, sulfonatoalkoxy, glyme, and glyme alcohol pendant chains. Iodization of EDOP and ProDOP via iodo-decarboxylation afforded iodo-functionalized derivatives useful for subsequent aryl coupling chemistry. N-Protection and formylation of EDOP, followed by Knoevenagel condensation of the resultant 2-formyl-EDOP with aryl acetonitrile derivatives, led to 1-cyano-2-(2-(3,4-ethylenedioxy-pyrryl))-1-(2-thienyl)vinylene (23) (Th-CNV-EDOP) and 1-cyano-2-(2-(3,4-ethylenedioxypyrryl))-1-(2-(3,4-ethylenedioxythienyl)vinylene (26) (EDOT-CNV-EDOP). A 14-crown-4-ether 34 based dioxypyrrole was synthesized with a cavity potentially useful for lithium ion coordination and sensing in the resultant electroactive polymer. C-Alkylated ProDOPs (43a, 43b, and 43c) containing octyl, ethylhexyl, and dioctyl substituents appended to the central methylene of the propylene bridge, were prepared as monomers for potentially soluble pi -conjugated polymers.

  DOI：

  10.1021/jo001620l