2-(1,4,7,10-Tetraazacyclododec-1-yl)propanol | 138884-13-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(1,4,7,10-Tetraazacyclododec-1-yl)propanol
• 英文别名: 2-(1,4,7,10-Tetrazacyclododec-1-yl)propan-1-ol
• CAS: 138884-13-6
• 化学式: C₁₁H₂₆N₄O
• 分子量: 230.354
• InChiKey: UTOPCRMLUWTQCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  59.6
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  溴乙酸 、 2-(1,4,7,10-Tetraazacyclododec-1-yl)propanol 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 以77%的产率得到2,2',2''-(10-(1-Hydroxypropan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid
  参考文献：
  名称：

  Synthesis of gadolinium (±)-10-(1-hydroxypropan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyltriacetate via tribenzyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate

  摘要：

  The synthesis of monogadolinium 10-(1-hydroxypropan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyltriacetate 12 has been achieved through a multistep sequence. The key step in the synthesis was the reaction of the previously unknown tribenzyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate 6 with ethyl 2-(trifluoromethylsulphonyloxy)propionate 4 to give 7. Reduction of 7 with LiBH4/9-OMe-BBN, followed by hydrogenolysis of the protecting groups (Z groups) yielded 2-(1,4,7,10-tetraazacyclododec-1-yl)propanol 10. The monosubstituted macrocycle 10 was alkylated with bromoacetic acid and then complexed with gadolinium oxide to yield the title compound.

  DOI：

  10.1039/p19910003329
• 作为产物：
  描述：

  Tribenzyl 10-<1-(Ethoxycarbonyl)ethyl>-1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate 在 palladium on activated charcoal 锂硼氢 、 9-OMe-BBN 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 32.0h， 生成 2-(1,4,7,10-Tetraazacyclododec-1-yl)propanol
  参考文献：
  名称：

  Synthesis of gadolinium (±)-10-(1-hydroxypropan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyltriacetate via tribenzyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate

  摘要：

  The synthesis of monogadolinium 10-(1-hydroxypropan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyltriacetate 12 has been achieved through a multistep sequence. The key step in the synthesis was the reaction of the previously unknown tribenzyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate 6 with ethyl 2-(trifluoromethylsulphonyloxy)propionate 4 to give 7. Reduction of 7 with LiBH4/9-OMe-BBN, followed by hydrogenolysis of the protecting groups (Z groups) yielded 2-(1,4,7,10-tetraazacyclododec-1-yl)propanol 10. The monosubstituted macrocycle 10 was alkylated with bromoacetic acid and then complexed with gadolinium oxide to yield the title compound.

  DOI：

  10.1039/p19910003329

文献信息

• MACROCYCLIC CHELATING AGENTS AND CHELATES THEREOF
  申请人：BRACCO INDUSTRIA CHIMICA Società per Azioni

  公开号：EP0440606A1

  公开（公告）日：1991-08-14
• WO1989005802A1
  申请人：——

  公开号：WO1989005802A1

  公开（公告）日：1989-06-29
• Synthesis of gadolinium (±)-10-(1-hydroxypropan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyltriacetate via tribenzyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate
  作者：J. Siva Prasad、Frank J. Okuniewicz、Edward J. Delaney、Douglas D. Dischino

  DOI：10.1039/p19910003329

  日期：——

  The synthesis of monogadolinium 10-(1-hydroxypropan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyltriacetate 12 has been achieved through a multistep sequence. The key step in the synthesis was the reaction of the previously unknown tribenzyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate 6 with ethyl 2-(trifluoromethylsulphonyloxy)propionate 4 to give 7. Reduction of 7 with LiBH4/9-OMe-BBN, followed by hydrogenolysis of the protecting groups (Z groups) yielded 2-(1,4,7,10-tetraazacyclododec-1-yl)propanol 10. The monosubstituted macrocycle 10 was alkylated with bromoacetic acid and then complexed with gadolinium oxide to yield the title compound.