dipropylcarbamoylmethoxyacetic acid | 290309-79-4

• 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: dipropylcarbamoylmethoxyacetic acid
• 英文别名: [2-(Dipropylamino)-2-oxoethoxy]acetic acid；2-[2-(dipropylamino)-2-oxoethoxy]acetic acid
• CAS: 290309-79-4
• 化学式: C₁₀H₁₉NO₄
• mdl: MFCD14618911
• 分子量: 217.265
• InChiKey: DAPQRVHYWNCVIC-UHFFFAOYSA-N

物化性质

• 熔点：
  55-56 °C
• 沸点：
  383.3±22.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dipropylcarbamoylmethoxyacetic acid 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、482.63 kPa 条件下， 反应 102.0h， 生成 {[(S)-1-(2-{2-[2-(2-Dipropylcarbamoylmethoxy-acetylamino)-acetylamino]-acetylamino}-acetyl)-pyrrolidine-2-carbonyl]-amino}-acetic acid
  参考文献：
  名称：

  Cation Dependence of Chloride Ion Complexation by Open-Chained Receptor Molecules in Chloroform Solution

  摘要：

  Seventeen peptides, most having the sequence GGGPGGG, but differing in the C- and N-terminal ends, have been studied as anion-complexing agents. These relatively simple, open-chained peptide systems interact with both chloride and the associated cation. Changes, in the N- and C-terminal side chains appear to make little difference in the efficacy of binding. NMR studies suggest that the primary interactions involve amide NH contacts with the chloride anion, and CD spectral analyses suggest a concomitant conformational change upon binding. Changes in binding constants, which are expected in different solvents, also suggest selective solvent interactions with the unbound host that helps to preorganize the open-chained peptide system. Significant differences are apparent in complexation strengths when the heptapeptide chain is shortened or lengthened or when the relative position of proline within the heptapeptide is varied.

  DOI：

  10.1021/ja0558894
• 作为产物：
  描述：

  二甘醇酐 、 二正丙胺 以 四氢呋喃 为溶剂， 反应 48.0h， 以75%的产率得到dipropylcarbamoylmethoxyacetic acid
  参考文献：
  名称：

  The C-and N-terminal residues of synthetic heptapeptide ion channels influence transport efficacy through phospholipid bilayers

  摘要：

  合成肽R2N-COCH2OCH2CO-Gly-Gly-Gly-Pro-Gly-Gly-Gly-OR′在R为n-十八烷基且R′为苄基时，对Cl−相对于K+表现出选择性。目前已制备出十九种七肽，其中N端和C端残基有所不同。所有N端残基均为二烷基，而C端链为酯、二级酰胺或三级酰胺。N端锚和C端苄基不同的化合物如下：1，R = n-丙基；2，R = n-己基；3，R = n-戊基；4，R = n-癸基；5，R = n-十二烷基；6，R = n-十四烷基；7，R = n-十六烷基；8，R = n-十八烷基。化合物9–19中R = n-十八烷基，C端残基如下：9，OR′ = OCH2CH3；10，OR′ = OCH(CH3)2；11，OR′ = O(CH2)6CH3；12，OR′ = OCH2–c-C6H11；13，OR′ = O(CH2)9CH3；14，OR′ = O(CH2)17CH3；15，NR′2 = N[(CH2)6CH3]2；16，NHR′ = NH(CH2)9CH3；17，NR′2 = N[(CH2)9CH3]2；18，NHR′ = NH(CH2)17CH3；19，NR′2 = N[(CH2)17CH3]2。观察到的最高阴离子转运活性如下：对于N端残基变量的苄基酯，i.e.1–8，化合物3活性最强。对于C18锚定的酯10–14，n-庚基酯11活性最强。对于C18锚定的C端酰胺15–19，二-n-癸酰胺17活性最强。结论是C端和N端锚对双层膜中的通道功能十分重要，但只有其中一个锚定基团占主导时活性才存在。

  DOI：

  10.1039/b417091c

文献信息

• The Selective Reaction of Primary Amines with Carbonyl Imidazole Containing Compounds:  Selective Amide and Carbamate Synthesis
  作者：Steve P. Rannard、Nicola J. Davis

  DOI：10.1021/ol006020n

  日期：2000.7.1

  A new highly selective synthesis of amides and carbamates is described. In both cases the syntheses involve the formation of carbonyl imidazole intermediates which subsequently undergo previously unreported selective reactions with primary amines. Acid imidazolides with sufficient chain length will exclusively react with primary amines even in the presence of secondary and tertiary functionality. The

  描述了酰胺和氨基甲酸酯的新的高选择性合成。在两种情况下，合成都涉及形成羰基咪唑中间体，该中间体随后与伯胺进行先前未报道的选择性反应。即使在存在仲和叔官能度的情况下，具有足够链长的酸咪唑啉化物也将仅与伯胺反应。仲或叔醇的咪唑羧酸酯还与伯胺选择性反应，形成受控的氨基甲酸酯结构。
• Gamma radiolysis of hydrophilic diglycolamide ligands in concentrated aqueous nitrate solution
  作者：Gregory P. Horne、Andreas Wilden、Stephen P. Mezyk、Liam Twight、Michelle Hupert、Andrea Stärk、Willem Verboom、Bruce J. Mincher、Giuseppe Modolo

  DOI：10.1039/c9dt03918j

  日期：——

  and (iii) radiolysis is driven by hydroxyl and nitrate radical oxidation chemistry moderated by secondary degradation product scavenging reactions. Overall, the radiolysis of hydrophilic DGAs in concentrated, aqueous nitrate solutions is significantly slower and less structurally sensitive than under pure water conditions, similar to their lipophilic analogs. Acid hydrolysis, not radiolysis, is expected

  在中性pH，浓硝酸水溶液条件下，研究了一系列亲水性二甘醇酰胺（DGA：TEDGA，Me-TEDGA，Me 2 -TEDGA和TPDGA）的辐射化学。先进的分析技术和多尺度建模计算支持的稳态伽马和时间分辨脉冲电子辐照实验相结合，证明：（i）所研究的亲水DGA经历一阶衰减，平均剂量常数为。 （-3.18±0.23）×10 -6 Gy -1 ; （ii）它们的降解产物分布类似于纯水条件下的分布，只是出现了NO x加合物; （iii）通过二级降解产物清除反应调节的羟基和硝酸根自由基氧化化学作用来驱动放射分解。总的来说，与纯脂条件下相比，在纯硝酸盐水溶液中亲水性DGA的辐射分解要慢得多，结构敏感性也要低得多，这与它们的亲脂类似物类似。酸水解而不是放射水解有望限制其使用寿命。这些发现对于将亲水性DGA用作act系元素水相汽提和阻滞剂是很有希望的，因为在设想的大规模工艺条件下存在高浓度的硝酸盐。
• Cation Dependence of Chloride Ion Complexation by Open-Chained Receptor Molecules in Chloroform Solution
  作者：Robert Pajewski、Riccardo Ferdani、Jolanta Pajewska、Ruiqiong Li、George W. Gokel

  DOI：10.1021/ja0558894

  日期：2005.12.1

  Seventeen peptides, most having the sequence GGGPGGG, but differing in the C- and N-terminal ends, have been studied as anion-complexing agents. These relatively simple, open-chained peptide systems interact with both chloride and the associated cation. Changes, in the N- and C-terminal side chains appear to make little difference in the efficacy of binding. NMR studies suggest that the primary interactions involve amide NH contacts with the chloride anion, and CD spectral analyses suggest a concomitant conformational change upon binding. Changes in binding constants, which are expected in different solvents, also suggest selective solvent interactions with the unbound host that helps to preorganize the open-chained peptide system. Significant differences are apparent in complexation strengths when the heptapeptide chain is shortened or lengthened or when the relative position of proline within the heptapeptide is varied.
• The C-and N-terminal residues of synthetic heptapeptide ion channels influence transport efficacy through phospholipid bilayers
  作者：Natasha Djedovi?、Riccardo Ferdani、Egan Harder、Jolanta Pajewska、Robert Pajewski、Michelle E. Weber、Paul H. Schlesinger、George W. Gokel

  DOI：10.1039/b417091c

  日期：——

  The synthetic peptide, R2N-COCH2OCH2CO-Gly-Gly-Gly-Pro-Gly-Gly-Gly-OR′, was shown to be selective for Cl− over K+ when R is n-octadecyl and R′ is benzyl. Nineteen heptapeptides have now been prepared in which the N-terminal and C-terminal residues have been varied. All of the N-terminal residues are dialkyl but the C-terminal chains are esters, 2° amides, or 3° amides. The compounds having varied N-terminal anchors and C-terminal benzyl groups are as follows: 1, R = n-propyl; 2, R = n-hexyl; 3, R = n-octyl; 4, R = n-decyl; 5, R = n-dodecyl; 6, R = n-tetradecyl; 7, R = n-hexadecyl; 8, R = n-octadecyl. Compounds 9–19 have R = n-octadecyl and C-terminal residues as follows: 9, OR′ = OCH2CH3; 10, OR′ = OCH(CH3)2; 11, OR′ = O(CH2)6CH3; 12, OR′ = OCH2–c-C6H11; 13, OR′ = O(CH2)9CH3; 14, OR′ = O(CH2)17CH3; 15, NR′2 = N[(CH2)6CH3]2; 16, NHR′ = NH(CH2)9CH3; 17, NR′2 = N[(CH2)9CH3]2; 18, NHR′ = NH(CH2)17CH3; 19, NR′2 = N[(CH2)17CH3]2. The highest anion transport activities were observed as follows. For the benzyl esters whose N-terminal residues were varied, i.e.1–8, compound 3 was most active. For the C18 anchored esters 10–14, n-heptyl ester 11 was most active. For the C18 anchored, C-terminal amides 15–19, di-n-decylamide 17 was most active. It was concluded that both the C-and N-terminal anchors were important for channel function in the bilayer but that activity was lost unless only one of the two anchoring groups was dominant.

  合成肽R2N-COCH2OCH2CO-Gly-Gly-Gly-Pro-Gly-Gly-Gly-OR′在R为n-十八烷基且R′为苄基时，对Cl−相对于K+表现出选择性。目前已制备出十九种七肽，其中N端和C端残基有所不同。所有N端残基均为二烷基，而C端链为酯、二级酰胺或三级酰胺。N端锚和C端苄基不同的化合物如下：1，R = n-丙基；2，R = n-己基；3，R = n-戊基；4，R = n-癸基；5，R = n-十二烷基；6，R = n-十四烷基；7，R = n-十六烷基；8，R = n-十八烷基。化合物9–19中R = n-十八烷基，C端残基如下：9，OR′ = OCH2CH3；10，OR′ = OCH(CH3)2；11，OR′ = O(CH2)6CH3；12，OR′ = OCH2–c-C6H11；13，OR′ = O(CH2)9CH3；14，OR′ = O(CH2)17CH3；15，NR′2 = N[(CH2)6CH3]2；16，NHR′ = NH(CH2)9CH3；17，NR′2 = N[(CH2)9CH3]2；18，NHR′ = NH(CH2)17CH3；19，NR′2 = N[(CH2)17CH3]2。观察到的最高阴离子转运活性如下：对于N端残基变量的苄基酯，i.e.1–8，化合物3活性最强。对于C18锚定的酯10–14，n-庚基酯11活性最强。对于C18锚定的C端酰胺15–19，二-n-癸酰胺17活性最强。结论是C端和N端锚对双层膜中的通道功能十分重要，但只有其中一个锚定基团占主导时活性才存在。