5,6-dihydro-11,12-didehydrodibenzo[a,e][8]annulen-5-yl 4-methylpiperazine-1-carboxylate | 1443674-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5,6-dihydro-11,12-didehydrodibenzo[a,e][8]annulen-5-yl 4-methylpiperazine-1-carboxylate
• 英文别名: 2-Tricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-ynyl 4-methylpiperazine-1-carboxylate
• CAS: 1443674-44-9
• 化学式: C₂₂H₂₂N₂O₂
• 分子量: 346.429
• InChiKey: PAWPQSSPPWPJLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-叠氮基乙醇 、 5,6-dihydro-11,12-didehydrodibenzo[a,e][8]annulen-5-yl 4-methylpiperazine-1-carboxylate 以 甲醇 为溶剂， 生成 、
  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：

  N-甲基哌嗪 、 11,12-didehydro-5,6-dihydrodibenzo[a,e]cycloocten-5-yl carbonic acid 4-nitrophenyl ester 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以99%的产率得到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