(1,4,7,10-四氮杂-环十二-1-基)-烯丙基乙酸酯 | 1023970-58-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (1,4,7,10-四氮杂-环十二-1-基)-烯丙基乙酸酯
• 英文名称: (1,4,7,10-tetraaza-cyclododec-1-yl)-acetic acid allyl ester
• 英文别名: 1,4,7,10-tetraazacyclododecane-1-yl-acetic acid allyl ester；(1,4,7,10Tetraaza-cyclododec-1-yl)-acetic acid allyl ester；prop-2-enyl 2-(1,4,7,10-tetrazacyclododec-1-yl)acetate
• CAS: 1023970-58-2
• 化学式: C₁₃H₂₆N₄O₂
• 分子量: 270.375
• InChiKey: MLBRGPOWBHLFRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  65.6
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (1,4,7,10-四氮杂-环十二-1-基)-烯丙基乙酸酯 在 N-甲基吗啉 、 四(三苯基膦)钯 、 三异丙基硅烷 、 水 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 21.0h， 生成 1,4,7,10-四氮杂环十二烷-1,4,7,10-四乙酸
  参考文献：
  名称：

  DOTA-tris(OPp ester) as a bifunctional prochelator for the preparation of DOTA–peptide conjugates

  摘要：

  Peptides containing the chelator DOTA have gained importance for molecular imaging and therapy with radionuclides. However, all synthons described for the convergent solid phase synthesis of DOTA-peptide conjugates show windows of stability that are too narrow to allow a clean and convergent deprotection process. The synthesis of the new prochelator DOTA-tris(OPp ester) starting from cyclen is reported. Using this prochelator for the synthesis of several DOTA peptide conjugates revealed that its cleavage-in contrast to the cleavage of DOTA-tris(tBu ester) conjugates-does not require an extended deprotection time, and therefore results in clean and homogenous products. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.10.007
• 作为产物：
  描述：

  氯乙酸丙烯酯 、 轮环藤宁 以 氯仿 为溶剂， 反应 6.0h， 以66%的产率得到(1,4,7,10-四氮杂-环十二-1-基)-烯丙基乙酸酯
  参考文献：
  名称：

  Improved syntheses and applicability of different DOTA building blocks for multiply derivatized scaffolds

  摘要：

  DOTA (1,4,7,10-tetraazacyclodocecane-N,N',N",N'''-tetraacetic acid), which forms extremely stable complexes with a large number of metal ions, is one of the most important and most commonly used chelators for in vivo applications such as cancer diagnosis and therapy. However, many of the published synthesis protocols for DOTA derivatives are complicated and give the products in low yields. Here we report improved synthesis routes for tris-tBu-DOTA, tris-benzyl-DOTA, and thiol-DOTA, and also describe the synthesis of the novel compound tris-4-nitro-benzyl-DOTA. In addition, we determined the applicability of the DOTA derivatives tris-tBu-DOTA, thiol-DOTA, tris-benzyl-DOTA, tris-4-nitrobenzyl-DOTA, tris-allyl-DOTA, DOTA-PFP-ester, and DOTA-PNP-ester for multimerization reactions using amino functionalized PAMAM dendrimers of different sizes. Thiol-DOTA was found to be the best compound for efficient reactions with dendritic scaffolds generating highly homogeneous DOTA-multimers. This DOTA derivative could be quantitatively conjugated to a 128-mer dendrimer. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.044

文献信息

• DOTA-tris(OPp ester) as a bifunctional prochelator for the preparation of DOTA–peptide conjugates
  作者：Mazen Jamous、Uwe Haberkorn、Walter Mier

  DOI：10.1016/j.tetlet.2012.10.007

  日期：2012.12

  Peptides containing the chelator DOTA have gained importance for molecular imaging and therapy with radionuclides. However, all synthons described for the convergent solid phase synthesis of DOTA-peptide conjugates show windows of stability that are too narrow to allow a clean and convergent deprotection process. The synthesis of the new prochelator DOTA-tris(OPp ester) starting from cyclen is reported. Using this prochelator for the synthesis of several DOTA peptide conjugates revealed that its cleavage-in contrast to the cleavage of DOTA-tris(tBu ester) conjugates-does not require an extended deprotection time, and therefore results in clean and homogenous products. (C) 2012 Published by Elsevier Ltd.
• Improved syntheses and applicability of different DOTA building blocks for multiply derivatized scaffolds
  作者：C. Wängler、B. Wängler、M. Eisenhut、U. Haberkorn、W. Mier

  DOI：10.1016/j.bmc.2007.11.044

  日期：2008.3

  DOTA (1,4,7,10-tetraazacyclodocecane-N,N',N",N'''-tetraacetic acid), which forms extremely stable complexes with a large number of metal ions, is one of the most important and most commonly used chelators for in vivo applications such as cancer diagnosis and therapy. However, many of the published synthesis protocols for DOTA derivatives are complicated and give the products in low yields. Here we report improved synthesis routes for tris-tBu-DOTA, tris-benzyl-DOTA, and thiol-DOTA, and also describe the synthesis of the novel compound tris-4-nitro-benzyl-DOTA. In addition, we determined the applicability of the DOTA derivatives tris-tBu-DOTA, thiol-DOTA, tris-benzyl-DOTA, tris-4-nitrobenzyl-DOTA, tris-allyl-DOTA, DOTA-PFP-ester, and DOTA-PNP-ester for multimerization reactions using amino functionalized PAMAM dendrimers of different sizes. Thiol-DOTA was found to be the best compound for efficient reactions with dendritic scaffolds generating highly homogeneous DOTA-multimers. This DOTA derivative could be quantitatively conjugated to a 128-mer dendrimer. (C) 2007 Elsevier Ltd. All rights reserved.