4-nitrophenyl [2,3,8,9-tetrakis(2-hydroxyethoxy)-5,6-dihydro-11,12-didehydrodibenzo[a,e][8]annulen-5-yl] carbonate | 1443674-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-nitrophenyl [2,3,8,9-tetrakis(2-hydroxyethoxy)-5,6-dihydro-11,12-didehydrodibenzo[a,e][8]annulen-5-yl] carbonate
• 英文别名: (4-Nitrophenyl) [6,7,14,15-tetrakis(2-hydroxyethoxy)-2-tricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-ynyl] carbonate
• CAS: 1443674-36-9
• 化学式: C₃₁H₃₁NO₁₃
• 分子量: 625.586
• InChiKey: XBQXWVPPHVKMOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  199
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 4-nitrophenyl [2,3,8,9-tetrakis(2-hydroxyethoxy)-5,6-dihydro-11,12-didehydrodibenzo[a,e][8]annulen-5-yl] carbonate 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以94%的产率得到2,3,8,9-tetrakis(2-hydroxyethoxy)-5,6-dihydro-11,12-didehydrodibenzo[a,e][8]annulen-5-yl 4-methylpiperazine-1-carboxylate
  参考文献：
  名称：

  Synthesis of Tetra(2-hydroxyethoxy)-Substituted Dibenzocyclooctyne Derivatives as Novel, Highly Hydrophilic Tool Compounds for Strain-Promoted Alkyne-Azide Cycloaddition Applications

  摘要：

  The synthesis of a novel, hydrophilic dibenzocyclooctyne derivative for strain-promoted alkyne-azide cycloaddition (SPAAC) is described. Starting from 2-(3,4-dimethoxyphenyl)acetaldehyde, the corresponding activated carbonate of 2,3,8,9-tetrakis(2-hydroxyethoxy)-5,6-dihydro-11,12-didehydrodibenzo[a,e][8]annulene, termed THE-DIBO, was prepared in seven steps and 24% overall yield. A water-soluble THE-DIBO analogue showed a k(2) value of (21.9 +/- 0.2) x 10(-2) M-1 s(-1) for SPAAC with 2-azidoethanol in water. The high hydrophilicity and steric bulk of THE-DIBO derivatives should to suppress nonspecific thiol-yne addition of proteins to strained alkynes observed for SPAAC labeling in complex proteomes.

  DOI：

  10.1055/s-0032-1316875
• 作为产物：
  描述：

  2',3',2'',3''-tetramethoxy-2,3:6,7-dibenzo-9-oxabicyclo<3.3.1>nona-2,6-diene 在 吡啶 、 咪唑 、 正丁基锂 、 三溴化硼 、 溴-1,4-二氧六环复合物 、 caesium carbonate 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 119.5h， 生成 4-nitrophenyl [2,3,8,9-tetrakis(2-hydroxyethoxy)-5,6-dihydro-11,12-didehydrodibenzo[a,e][8]annulen-5-yl] carbonate
  参考文献：
  名称：

  Synthesis of Tetra(2-hydroxyethoxy)-Substituted Dibenzocyclooctyne Derivatives as Novel, Highly Hydrophilic Tool Compounds for Strain-Promoted Alkyne-Azide Cycloaddition Applications

  摘要：

  The synthesis of a novel, hydrophilic dibenzocyclooctyne derivative for strain-promoted alkyne-azide cycloaddition (SPAAC) is described. Starting from 2-(3,4-dimethoxyphenyl)acetaldehyde, the corresponding activated carbonate of 2,3,8,9-tetrakis(2-hydroxyethoxy)-5,6-dihydro-11,12-didehydrodibenzo[a,e][8]annulene, termed THE-DIBO, was prepared in seven steps and 24% overall yield. A water-soluble THE-DIBO analogue showed a k(2) value of (21.9 +/- 0.2) x 10(-2) M-1 s(-1) for SPAAC with 2-azidoethanol in water. The high hydrophilicity and steric bulk of THE-DIBO derivatives should to suppress nonspecific thiol-yne addition of proteins to strained alkynes observed for SPAAC labeling in complex proteomes.

  DOI：

  10.1055/s-0032-1316875