N-(propargyl)-1,4,7-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecan-10-ylacetamide | 1312185-53-7

• 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: N-(propargyl)-1,4,7-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecan-10-ylacetamide
• 英文别名: Tritert-butyl 10-[2-oxo-2-(prop-2-ynylamino)ethyl]-1,4,7,10-tetrazacyclododecane-1,4,7-tricarboxylate；tritert-butyl 10-[2-oxo-2-(prop-2-ynylamino)ethyl]-1,4,7,10-tetrazacyclododecane-1,4,7-tricarboxylate
• CAS: 1312185-53-7
• 化学式: C₂₈H₄₉N₅O₇
• 分子量: 567.726
• InChiKey: GKVLSFXAXUFGRB-UHFFFAOYSA-N

物化性质

• 沸点：
  659.9±55.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,5-bis(azidomethyl)acridine 、 N-(propargyl)-1,4,7-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecan-10-ylacetamide 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 以55%的产率得到hexa-tert-butyl 10,10'-((((1,1'-(acridine-4,5-diylbis(methylene))bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene))bis(azanediyl))bis(2-oxoethane-2,1-diyl))bis(1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate)
  参考文献：
  名称：

  Fluorescent bis-cyclen tweezer receptors for inositol (1,4,5)-trisphosphate

  摘要：

  Herein, we report the development of two fluorescent sensors for inositol 1,4,5-trisphosphate (InsP(3)), containing either two free cyclen or zinc(II)/cyclen groups preorganized into a binding cleft. Preorganization was achieved using a rigid acridine backbone, which was also exploited for fluorescence signal transduction. In addition, click chemistry was used to facilitate receptor synthesis and produce triazole moieties that add to structural rigidity and recognition. In binding studies, both receptors were found to bind InsP(3) with high affinity (K-a = 0.5-1.0 x 10(6) M-1) in competitive media (1:1 methanol/water). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.092
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 轮环藤宁 在 potassium carbonate 、 三乙胺 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 48.0h， 生成 N-(propargyl)-1,4,7-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecan-10-ylacetamide
  参考文献：
  名称：

  Fluorescent bis-cyclen tweezer receptors for inositol (1,4,5)-trisphosphate

  摘要：

  Herein, we report the development of two fluorescent sensors for inositol 1,4,5-trisphosphate (InsP(3)), containing either two free cyclen or zinc(II)/cyclen groups preorganized into a binding cleft. Preorganization was achieved using a rigid acridine backbone, which was also exploited for fluorescence signal transduction. In addition, click chemistry was used to facilitate receptor synthesis and produce triazole moieties that add to structural rigidity and recognition. In binding studies, both receptors were found to bind InsP(3) with high affinity (K-a = 0.5-1.0 x 10(6) M-1) in competitive media (1:1 methanol/water). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.092

文献信息

• Fluorescent bis-cyclen tweezer receptors for inositol (1,4,5)-trisphosphate
  作者：Chi-Linh Do-Thanh、Meng M. Rowland、Michael D. Best

  DOI：10.1016/j.tet.2011.03.092

  日期：2011.5

  Herein, we report the development of two fluorescent sensors for inositol 1,4,5-trisphosphate (InsP(3)), containing either two free cyclen or zinc(II)/cyclen groups preorganized into a binding cleft. Preorganization was achieved using a rigid acridine backbone, which was also exploited for fluorescence signal transduction. In addition, click chemistry was used to facilitate receptor synthesis and produce triazole moieties that add to structural rigidity and recognition. In binding studies, both receptors were found to bind InsP(3) with high affinity (K-a = 0.5-1.0 x 10(6) M-1) in competitive media (1:1 methanol/water). (C) 2011 Elsevier Ltd. All rights reserved.