N,N'-(propane-1,3-diylbis{[(tert-butoxycarbonyl)imino]ethylene})bis(trifluoroacetamide) | 556082-11-2

• 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
• 英文名称: N,N'-(propane-1,3-diylbis{[(tert-butoxycarbonyl)imino]ethylene})bis(trifluoroacetamide)
• 英文别名: tert-butyl propane-1,3-diylbis(2-(2,2,2-trifluoroacetamido)ethylcarbamate)；Di-tert-butylpropane-1,3-diylbis(2-(2,2,2-trifluoroacetamido)-ethylcarbamate；tert-butyl N-[3-[(2-methylpropan-2-yl)oxycarbonyl-[2-[(2,2,2-trifluoroacetyl)amino]ethyl]amino]propyl]-N-[2-[(2,2,2-trifluoroacetyl)amino]ethyl]carbamate
• CAS: 556082-11-2
• 化学式: C₂₁H₃₄F₆N₄O₆
• 分子量: 552.515
• InChiKey: FQICKRLWFXXDPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N,N'-(propane-1,3-diylbis{[(tert-butoxycarbonyl)imino]ethylene})bis(trifluoroacetamide) 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以91%的产率得到2,2'-{propane-1,3-diylbis[(tert-butoxycarbonyl)imino]}diethan-1-amine
  参考文献：
  名称：

  A Facile Synthesis of Selectively Protected Linear Oligoamines

  摘要：

  一种方便的多克隆制备方法用于合成具有未保护的末端初级氨基团和中心次级氨基功能受到tert-丁氧羰基团保护的线性寡胺。同时，还开发了α，ω-双(三氟乙酰胺)中间体2的简单一锅制备方法。还讨论了新型选择性保护寡胺的NMR光谱。

  DOI：

  10.1135/cccc20030744
• 作为产物：
  描述：

  N,N'-二(2-氨乙基)-1,3-丙二胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 N,N'-(propane-1,3-diylbis{[(tert-butoxycarbonyl)imino]ethylene})bis(trifluoroacetamide)
  参考文献：
  名称：

  A Facile Synthesis of Selectively Protected Linear Oligoamines

  摘要：

  一种方便的多克隆制备方法用于合成具有未保护的末端初级氨基团和中心次级氨基功能受到tert-丁氧羰基团保护的线性寡胺。同时，还开发了α，ω-双(三氟乙酰胺)中间体2的简单一锅制备方法。还讨论了新型选择性保护寡胺的NMR光谱。

  DOI：

  10.1135/cccc20030744

文献信息

• Polyamines Inhibit Carbonic Anhydrases by Anchoring to the Zinc-Coordinated Water Molecule
  作者：Fabrizio Carta、Claudia Temperini、Alessio Innocenti、Andrea Scozzafava、Kai Kaila、Claudiu T. Supuran

  DOI：10.1021/jm1003667

  日期：2010.8.12

  Carbonic anhydrases (CAs, EC 4.2.1.1) are inhibited by sulfonamides, phenols, and coumarins. Polyamines such as spermine, spermidine, and many synthetic congeners are described to constitute a novel class of CA inhibitors (CAIs), interacting with the different CA isozymes with efficiency from the low nanomolar to millimolar range. The main structure activity relationship for these CAIs have been delineated: the length of the molecule, number of amine moieties, and their functionalization are the main parameters controlling activity. The X-ray crystal structure of the CA II spermine adduct allowed understanding of the inhibition mechanism. Spermine anchors to the nonprotein zinc ligand through a network of hydrogen bonds. Its distal amine moiety makes hydrogen bonds with residues Thr200 and Pro201, which further stabilize the adduct. Spermine binds differently compared to sulfonamides, phenols, or coumarins, rendering possible to develop CAIs with a diverse inhibition mechanism, profile, and selectivity for various isoforms.
• A Facile Synthesis of Selectively Protected Linear Oligoamines
  作者：Simona Koščová、Miloš Buděšínský、Jana Hodačová

  DOI：10.1135/cccc20030744

  日期：——

  A convenient multi-gram preparative method for the synthesis of linear oligoamines having the terminal primary amino groups unprotected and the central secondary amino functions protected with tert-butoxycarbonyl groups is presented. At the same time, simple one-pot preparation of the α,ω-bis(trifluoroacetamide) intermediates 2 has been developed. NMR spectra of the novel selectively protected oligoamines are also discussed.

  一种方便的多克隆制备方法用于合成具有未保护的末端初级氨基团和中心次级氨基功能受到tert-丁氧羰基团保护的线性寡胺。同时，还开发了α，ω-双(三氟乙酰胺)中间体2的简单一锅制备方法。还讨论了新型选择性保护寡胺的NMR光谱。