2,9-bis(hydroxymethyl)-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid | 214461-84-4

• 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
• 英文名称: 2,9-bis(hydroxymethyl)-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid
• 英文别名: 2-[4,7,10-Tris(carboxymethyl)-3,8-bis(hydroxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid
• CAS: 214461-84-4
• 化学式: C₁₈H₃₂N₄O₁₀
• 分子量: 464.473
• InChiKey: BIBBUBRDLVDCHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11.8
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  203
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  gadolinium(III) chloride hexahydrate 、 1-脱氧-1-(甲氨基)-D-葡萄糖醇 、 2,9-bis(hydroxymethyl)-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid 以 水 为溶剂， 以25%的产率得到[[2,9-bis(hydroxymethyl)-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetato(4-)]gadolinate(1-)]hydrogen*1-deoxy-1-(methylamino)-D-glucitol
  参考文献：
  名称：

  Gd(III) complexes of poly(hydroxymethyl)substituted derivatives of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid

  摘要：

  Gd(III) complexes of 1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid bearing two and four hydroxymethyl moieties on the cyclen ring were prepared to be studied as low toxicity MRI contrast agents. The key intermediates in the syntheses of the two ligands are the corresponding bis and tetrasubstituted cyclen derivatives. Bis(hydroxymetyl)cyclen was obtained according the so-called 'crab-like' cyclization procedure. Photoelectron transfer-induced tetramerization of (R)-2-(benzyloxymethyl)-N-(benzyl) aziridine stereoselectively led to homochiral tetra(hydroxymethyl)cyclen. The X-ray crystal structure of the latter compound unambiguously proved the alike stereochemical configuration of the four stereogenic carbon atoms in the cyclen ring. Carboxymethylation of the cyclen derivatives followed by complexation with either GdCl3 or Gd(OAc)(3) afforded the target complexes. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0020-1693(01)00364-4

文献信息

• Gd(III) complexes of poly(hydroxymethyl)substituted derivatives of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid
  作者：Pier Lucio Anelli、Andrea Beltrami、Maurizio Franzini、Paola Paoli、Patrizia Rossi、Fulvio Uggeri、Mario Virtuani

  DOI：10.1016/s0020-1693(01)00364-4

  日期：2001.5

  Gd(III) complexes of 1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid bearing two and four hydroxymethyl moieties on the cyclen ring were prepared to be studied as low toxicity MRI contrast agents. The key intermediates in the syntheses of the two ligands are the corresponding bis and tetrasubstituted cyclen derivatives. Bis(hydroxymetyl)cyclen was obtained according the so-called 'crab-like' cyclization procedure. Photoelectron transfer-induced tetramerization of (R)-2-(benzyloxymethyl)-N-(benzyl) aziridine stereoselectively led to homochiral tetra(hydroxymethyl)cyclen. The X-ray crystal structure of the latter compound unambiguously proved the alike stereochemical configuration of the four stereogenic carbon atoms in the cyclen ring. Carboxymethylation of the cyclen derivatives followed by complexation with either GdCl3 or Gd(OAc)(3) afforded the target complexes. (C) 2001 Elsevier Science B.V. All rights reserved.
• Chelated complexes of paramagnetic metals with low toxicity
  申请人：BRACCO S.p.A.

  公开号：EP0872479B1

  公开（公告）日：2002-09-04
• US6149890A
  申请人：——

  公开号：US6149890A

  公开（公告）日：2000-11-21
• US6177562B1
  申请人：——

  公开号：US6177562B1

  公开（公告）日：2001-01-23
• USRE38329E1
  申请人：——

  公开号：USRE38329E1

  公开（公告）日：2003-11-25