1-carboxymethyl-1,4-diazabicyclo[2.2.2]octane inner salt | 152063-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-carboxymethyl-1,4-diazabicyclo[2.2.2]octane inner salt
• 英文别名: N-carboxymethyl-1,4-diazabicyclo[2.2.2]octane；DABCO mono betaine
• CAS: 152063-17-7
• 化学式: C₈H₁₄N₂O₂
• 分子量: 170.211
• InChiKey: SZQSNLXGYAENBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.12
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-carboxymethyl-1,4-diazabicyclo[2.2.2]octane inner salt 、 方酸 以 甲醇 、 水 为溶剂， 生成 2-(1,4-diazabicyclo[2.2.2]octan-1-ium-1-yl)acetate compound with 3,4-dihydroxycyclobut-3-ene-1,2-dione (1:1)
  参考文献：
  名称：

  Interactions of squaric acid with DABCO mono-betaine: Structural, spectroscopic and calculation studies

  摘要：

  The 1:1 complex of squaric acid (3,4-dihydroxy-3-cyclobutene-1,2-dion) with DABCO mono-betaine (1-carboxymethyl-1,4-diazabicyclo[2.2.2]octane inner salt), 1, has been characterized by single-crystal X-ray analysis, FTIR and NMR spectroscopies and by DFT calculations. The crystal of 1 is triclinic, space group P (1) over bar. Short COOH center dot center dot center dot O and N-H center dot center dot center dot O hydrogen bonds of 2.445(2) and 2.582(2) angstrom. respectively, link the diprotonated DABCO mono-betaine dications and squarate dianions into chain. The structure is additionally stabilized by the N+center dot center dot center dot O electrostatic interactions and weak C-H center dot center dot center dot O hydrogen bonds. The FTIR spectrum shows two broad absorptions in the 3000-2000 cm(-1) region assigned to the nu N-H center dot center dot center dot O vibration and in the 1900-500 cm(-1) region attributed to the nu(OHO) and gamma(OHO) vibrations of the short hydrogen bonds. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.12.041
• 作为产物：
  描述：

  Ethyl 2-(4-aza-1-azoniabicyclo[2.2.2]octan-1-yl)acetate 在 Amberlite IRA 400 anion exchange resin 作用下， 以 水 为溶剂， 反应 1.0h， 以10 g的产率得到1-carboxymethyl-1,4-diazabicyclo[2.2.2]octane inner salt
  参考文献：
  名称：

  次氯酸对次胺在甲基4-脱氧-β-L-苏-hex-4-enopyranosiduronic酸氧化中的催化效率和稳定性

  摘要：

  叔胺可通过次氯酸（HOCl）有效催化不饱和有机物的氧化。然而，作为反应性物种自发形成的季氯铵阳离子经常经历平行自分解，这增加了所需的催化剂用量。因此，在HOCl的存在下，另一种可能的工业催化剂1,4-二氮杂双环[2.2.2]辛烷（DABCO）会在几秒钟内分解。在本文中，我们表明用烷基取代DABCO的一个氨基（在这种情况下用羧甲基）完全稳定了多环氯铵阳离子的自分解。氮的催化效率在弱酸条件（pH 3-6）下，-羧甲基-1,4-二氮杂双环[2.2.2]辛烷值与DABCO相似，或仅略低于DABCO。尽管我们仅研究了甲基4-脱氧-β-L-苏-hex-4-enopyranosiduronicuronic的氧化，但关于N-烷基化对催化剂稳定性和活性的影响的主要结论应该可以转化为任何其他底物的催化转化氯化氢。

  DOI：

  10.1016/j.mcat.2019.110413

文献信息

• DABCO mono-betaine hydrate studied by X-ray diffraction, DFT calculations and spectroscopic methods
  作者：P. Barczyński、Z. Dega-Szafran、A. Katrusiak、W. Perdoch、M. Szafran

  DOI：10.1016/j.molstruc.2009.05.050

  日期：2009.9

  A new DABCO mono-betaine (1-carboxymethyl-1,4-diazabicyclo[2.2.2]octane inner salt) has been synthesized. It crystallizes as monohydrate in orthorhombic space group Pmn2(1). The DABCO mono-betaine and water molecules are located on a mirror plane. The water molecules link DABCO mono-betaine into linear chains through the H-O-H center dot center dot center dot OOC and H-O-H center dot center dot center dot N hydrogen bonds of 2.709(2) and 2.875(2) angstrom. The structure of the title compound optimized at B3LYP/6-31G(d,p) level of theory is consistent with X-ray diffraction. The absorption bands in the FTIR spectrum have been assigned. The calculated magnetic isotropic shielding tensors confirm the assignments of the C-13 NMR resonance signals. (C) 2009 Elsevier B.V. All rights reserved.