N,N'-Bis(1-deoxy-D-glucitolyl)ethylenediamine | 87157-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N'-Bis(1-deoxy-D-glucitolyl)ethylenediamine
• 英文别名: N,N'-ethylenedi-(1-imino-1-deoxy-D-glucitol)；1,2-bis(1-deoxy-D-glucitol-1-ylamino)ethane；1,2-bis-(D-gluco-2,3,4,5,6-pentahydroxy-hexylamino)-ethane；1.2-Bis-D-glucamino-aethan；1,2-Bis-(D-gluco-2,3,4,5,6-pentahydroxy-hexylamino)-aethan；N.N'-Bis-(D-gluco-2.3.4.5.6-pentahydroxy-hexyl)-aethylendiamin；(2R,3R,4R,5S)-6-[2-[[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]ethylamino]hexane-1,2,3,4,5-pentol
• CAS: 87157-57-1
• 化学式: C₁₄H₃₂N₂O₁₀
• 分子量: 388.415
• InChiKey: SEQUYHNFILCATB-XKYMMBCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  226
• 氢给体数：
  12
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N,N'-Bis(1-deoxy-D-glucitolyl)ethylenediamine 、 辛基缩水甘油醚 以 水 、 乙腈 为溶剂， 反应 9.25h， 生成 N,N'-di[2-hydroxy-3-(2-ethyl)hexyloxypropyl]-N,N'-di(1-deoxyglucityl)-1,2-diaminoethane
  参考文献：
  名称：

  Gemini glycidyl ether adducts of polyhydroxyalkyl alkylenediamines

  摘要：

  公开号：

  EP1457481B1
• 作为产物：
  描述：

  (2R,3R,4R,5S)-6-{(E)-2-[(2S,3R,4R,5R)-2,3,4,5,6-Pentahydroxy-hex-(E)-ylideneamino]-ethylimino}-hexane-1,2,3,4,5-pentaol 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 N,N'-Bis(1-deoxy-D-glucitolyl)ethylenediamine
  参考文献：
  名称：

  超分子化学，62.配体和共底物对磷酸酯和DNA与镧系元素水解的影响† ‡

  摘要：

  已描述了通过提供具有增加数量的亲核基团的共底物或通过将相应的多元醇共价连接至更强的金属结合中心（如二氮杂冠醚）来增强镧系离子的催化活性的尝试。尽管对双（4-硝基苯基）磷酸酯（BNPP）和超螺旋质粒DNA水解的动力学影响只是中等程度，但它们对共底物结构和多元醇构型的依赖性明确表明它们参与了反应的缓慢步骤。因此，向LaCl 3溶液中添加葡萄糖酸会导致DNA切割从20％显着增加到71％​​。与二氮杂皇冠共价结合的萘单元对BNPP的影响很小水解，但再次将DNA水解从38％（RF II）提高到60％。使用溴化乙锭的荧光测定法对小牛胸腺DNA进行的初步亲和力测量显示，多胺对配体电荷的依赖性如先前观察到的那样。萘化合物的特征是高亲和力。初步的NMR数据表明，萘基单元插入到DNA中。

  DOI：

  10.1002/jlac.199619961109

文献信息

• Synthesis of nonionic reduced-sugar based bola amphiphiles and gemini surfactants with an α,ω-diamino-(oxa)alkyl spacer
  作者：Anno Wagenaar、Jan B.F.N. Engberts

  DOI：10.1016/j.tet.2007.08.023

  日期：2007.10

  Reduced-sugar based gemini surfactants with an alpha,omega-diamino-(oxa) alkyl spacer exhibit a rich pH-dependent aggregation behavior and are efficient DNA carriers in gene transfection. Herein, we describe an improved synthetic procedure for these amphiphiles. First, a series of novel nonionic bolaform amphiphiles with identical headgroups and alpha,omega-diamino-(oxa) alkyl spacers were synthesized by reductive aminations involving alpha,omega-diaminoalkanes and the appropriate sugars or aldehydes. The bolaform compounds were used as starting materials for the synthesis of the corresponding reduced-sugar based gemini surfactants in a reductive alkylation reaction employing a polymer-bound cyanoborohydride. A series of new gemini surfactants have been synthesized and characterized. (C) 2007 Elsevier Ltd. All rights reserved.
• The Reaction of Glucose with Some Amines
  作者：Eleanor Mitts、R. M. Hixon

  DOI：10.1021/ja01231a055

  日期：1944.3
• Reductive amination of aldohexoses with mono- and bifunctional alkyl amines: conversion of carbohydrates into EDTA type complexing agents
  作者：Hendrik Lammers、Joop A. Peters、Herman van Bekkum

  DOI：10.1016/s0040-4020(01)85293-5

  日期：1994.1

  It is shown by H-1 and C-13 NMR spectroscopy (1D and 2D) that beta-N-propylgalactosylamine (5a) is the major species present in an equimolar aqueous solution of D-galactose (1a) and propylamine (PA). In equimolar solutions of aldohexoses (1a-c) and ethylenediamine (EN) or 1,3-diaminopropane (DAP) in addition to mono- (9) and diglycosylamines (12) tetra-imidazole (8, n=1) and hexahydropyrimidine derivatives (8, n=2), respectively, are formed. Hydrogenation of equimolar solutions of aldohexoses (1a-c) and primary amines (PA, EN, and DAP) at 100 atm. and 50 degrees C, using 5% Pt on carbon as the catalyst, gave amino sugars 13-16 in good yields. Carboxymethylation of 14a-b resulted in sugar based EDTA type complexing agents (17a-b) with promising chelating abilities towards Cd(II) and Ca(II) at high pH.
• Gemini glycidyl ether adducts of polyhydroxyalkyl alkylenediamines
  申请人：AIR PRODUCTS AND CHEMICALS, INC.

  公开号：EP1457481B1

  公开（公告）日：2007-05-23
• Supramolecular Chemistry, 62. Ligand and Cosubstrate Effects on the Hydrolysis of Phosphate Esters and DNA with Lanthanoids
  作者：Jörg Rammo、Hans-Jörg Schneider

  DOI：10.1002/jlac.199619961109

  日期：1996.11

  an increasing number of nucleophilic groups or by attaching corresponding polyols covalently to stronger metal-binding centers like diazacrown ethers. Although the kinetic effects on the hydrolysis of bis(4-nitrophenyl) phosphate (BNPP) and of super-coiled plasmid DNA are only moderate, their dependence on cosubstrate structure and polyol configuration unambiguously demonstrates that these are involved

  已描述了通过提供具有增加数量的亲核基团的共底物或通过将相应的多元醇共价连接至更强的金属结合中心（如二氮杂冠醚）来增强镧系离子的催化活性的尝试。尽管对双（4-硝基苯基）磷酸酯（BNPP）和超螺旋质粒DNA水解的动力学影响只是中等程度，但它们对共底物结构和多元醇构型的依赖性明确表明它们参与了反应的缓慢步骤。因此，向LaCl 3溶液中添加葡萄糖酸会导致DNA切割从20％显着增加到71％​​。与二氮杂皇冠共价结合的萘单元对BNPP的影响很小水解，但再次将DNA水解从38％（RF II）提高到60％。使用溴化乙锭的荧光测定法对小牛胸腺DNA进行的初步亲和力测量显示，多胺对配体电荷的依赖性如先前观察到的那样。萘化合物的特征是高亲和力。初步的NMR数据表明，萘基单元插入到DNA中。