Methyl 2-Decylamidoacetate | 62248-80-0

• 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: Methyl 2-Decylamidoacetate
• 英文别名: Methyl 2-decanamidoacetate；methyl 2-(decanoylamino)acetate
• CAS: 62248-80-0
• 化学式: C₁₃H₂₅NO₃
• mdl: MFCD12563965
• 分子量: 243.346
• InChiKey: HOZZVVLREMJPBA-UHFFFAOYSA-N

物化性质

• 沸点：
  365.0±15.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.846
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2-Decylamidoacetate 在 lithium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 N-decanoylglycine
  参考文献：
  名称：

  Structure and Thermotropic Phase Behavior of a Homologous Series ofN-Acylglycines: Neuroactive and Antinociceptive Constituents of Biomembranes

  摘要：

  N-Acylglycines (NAGs) with different acyl chains have been found in the mammalian brain and other tissues. They exhibit significant biological and pharmacological properties and appear to play important roles in communication and signaling pathways within and between cells. In view of this, a homologous series of NAGs have been synthesized and characterized in the present study. Differential scanning calorimetric (DSC) studies show that the transition enthalpies and entropies of dry as well as hydrated NAGs exhibit a linear dependence on the acyl chain length. Most of the NAGs show a minor transition below the chain-melting phase transition, suggesting the presence of polymorphism in the solid state. Structures of N-myristoylglycine (NMG) and N-palmitoylglycine (NPG) were solved in monoclinic system with C2/c and P2(1) space groups, respectively. Analysis of the crystal structures show that NAGs are organized in a bilayer fashion, with head-to-head (and tail-to-tail) arrangement of molecules. The acyl chains in both structures are essentially perpendicular to the bilayer plane, which is consistent with a lack of oddeven alternation in the thermodynamic properties. The bilayer is stabilized by strong hydrogen bonding interactions between -COOH groups of the molecules from opposite leaflets as well as NH center dot center dot center dot O hydrogen bonds between the amide groups of adjacent molecules in the same leaflet and dispersion interactions among the acyl chains. Powder X-ray diffraction data show that the d-spacings for the NAGs with different acyl chains (n = 820) exhibit a linear dependence on the chain length, suggesting that all the NAGs investigated here adopt a similar packing arrangement in the crystal lattice. These observations are relevant for understanding the role of N-acylglycines in biological membranes.

  DOI：

  10.1021/cg500481u
• 作为产物：
  描述：

  正癸酸 在 草酰氯 、 碳酸氢钠 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 2.0h， 生成 Methyl 2-Decylamidoacetate
  参考文献：
  名称：

  Structure and Thermotropic Phase Behavior of a Homologous Series ofN-Acylglycines: Neuroactive and Antinociceptive Constituents of Biomembranes

  摘要：

  N-Acylglycines (NAGs) with different acyl chains have been found in the mammalian brain and other tissues. They exhibit significant biological and pharmacological properties and appear to play important roles in communication and signaling pathways within and between cells. In view of this, a homologous series of NAGs have been synthesized and characterized in the present study. Differential scanning calorimetric (DSC) studies show that the transition enthalpies and entropies of dry as well as hydrated NAGs exhibit a linear dependence on the acyl chain length. Most of the NAGs show a minor transition below the chain-melting phase transition, suggesting the presence of polymorphism in the solid state. Structures of N-myristoylglycine (NMG) and N-palmitoylglycine (NPG) were solved in monoclinic system with C2/c and P2(1) space groups, respectively. Analysis of the crystal structures show that NAGs are organized in a bilayer fashion, with head-to-head (and tail-to-tail) arrangement of molecules. The acyl chains in both structures are essentially perpendicular to the bilayer plane, which is consistent with a lack of oddeven alternation in the thermodynamic properties. The bilayer is stabilized by strong hydrogen bonding interactions between -COOH groups of the molecules from opposite leaflets as well as NH center dot center dot center dot O hydrogen bonds between the amide groups of adjacent molecules in the same leaflet and dispersion interactions among the acyl chains. Powder X-ray diffraction data show that the d-spacings for the NAGs with different acyl chains (n = 820) exhibit a linear dependence on the chain length, suggesting that all the NAGs investigated here adopt a similar packing arrangement in the crystal lattice. These observations are relevant for understanding the role of N-acylglycines in biological membranes.

  DOI：

  10.1021/cg500481u

文献信息

• A Macrocyclic Enzyme Model System. An Electrostatic-Hydrophobic Double-Field Catalysis by a [20]Paracyclophane in the Deacylation of<i>p</i>-Nitrophenyl Hexadecanoate
  作者：Yukito Murakami、Yasuhiro Aoyama、Kazuyuki Dobashi、Masaaki Kida

  DOI：10.1246/bcsj.49.3633

  日期：1976.12

  The catalytic functions of 10-oxo[20]paracyclophanyl-22(23)-methyltrimethylammonium chloride (1) in the hydrolysis and aminolysis reactions of p-nitrophenyl hexadecanoate (PNPP) were investigated in 1%(v/v)methanol–1%(v/v)dioxane-water over the pH 9–10 region at 40.0 °C and μ=0.2 (NaCl) with the initial PNPP concentration of 1.00×10−5 M. The paracyclophane (0.88×10−5 M) accelerated the hydrolysis of

  10-氧代[20]对环芳基-22(23)-甲基三甲基氯化铵(1)在1%(v/v)甲醇-1%对硝基苯十六酸酯(PNPP)水解和氨解反应中的催化作用(v/v) 二恶烷-水在 40.0 °C 和 μ=0.2 (NaCl) 的 pH 9–10 范围内，初始 PNPP 浓度为 1.00×10−5 M。对环烷 (0.88×10−5 M) 加速PNPP 在 pH 9.7 时水解一个数量级。在 PNPP 的 1-催化脱酰中乙醇胺或甘氨酸的存在导致进一步的速率提高。产物分析证实，PNPP 与胺的氨解反应导致了速率的提高。
• Glycopeptide derivatives
  申请人：——

  公开号：US20030008812A1

  公开（公告）日：2003-01-09

  Disclosed are derivatives of glycopeptide antibiotic compounds having at least one substituent of the formula: —R a —Y—R b —(Z) x where R a , R b , Y, Z and x are as defined, and having a group W at the glucose C-6 position, where W is as defined; and pharmaceutical compositions containing such glycopeptide derivatives. The disclosed glycopeptide derivatives are useful as antibacterial agents.

  揭示了具有至少一个取代基的糖肽抗生素化合物的衍生物，该取代基的公式为：—Ra—Y—Rb—（Z）x，其中Ra，Rb，Y，Z和x如定义所述，并在葡萄糖C-6位置具有W基团，其中W如定义所述;以及包含这种糖肽衍生物的药物组合物。揭示的糖肽衍生物可用作抗菌剂。
• Intermediate for preparing glycopeptide derivatives
  申请人：——

  公开号：US20040204346A1

  公开（公告）日：2004-10-14

  This invention provides compounds of the formula: 1 wherein A and B are as defined; and Fmoc is 9-fluorenylmethoxycarbonyl. Such compounds are useful as intermediates for preparing glycopeptide derivatives which are useful as antibiotics.

  该发明提供了以下式子的化合物：1其中A和B的定义如上；Fmoc是9-芴甲氧羰基。这些化合物可用作制备糖肽衍生物的中间体，这些糖肽衍生物可用作抗生素。
• Glycopeptide derivatives and pharmaceutical compositions containing the same
  申请人：——

  公开号：US20030060598A1

  公开（公告）日：2003-03-27

  Disclosed are derivatives of glycopeptide compounds having at least one substituent of the formula: —R a —Y—R b —(Z) x where R a , R b , Y, Z and x are as defined, and pharmaceutical compositions containing such glycopeptide derivatives. The disclosed glycopeptide derivatives are useful as antibacterial agents.

  本发明涉及一种含有至少一个配基的糖肽衍生物化合物，其配基的公式如下：—Ra—Y—Rb—(Z)x，其中Ra、Rb、Y、Z和x的定义如上所述，并且包含这种糖肽衍生物的药物组合物。所述的糖肽衍生物可用作抗菌剂。
• GLYCOPEPTIDE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
  申请人：Judice J. Kevin

  公开号：US20090215982A1

  公开（公告）日：2009-08-27

  Disclosed are derivatives of glycopeptide compounds having at least one substituent of the formula: —R a —Y—R b -(Z) x where R a , R b , Y, Z and x are as defined, and pharmaceutical compositions containing such glycopeptide derivatives. The disclosed glycopeptide derivatives are useful as antibacterial agents.

  本发明涉及具有至少一个以下式子的取代基的糖肽化合物衍生物：—Ra—Y—Rb-(Z)x，其中Ra、Rb、Y、Z和x如定义所述，并且含有这种糖肽衍生物的药物组合物。所述的糖肽衍生物可用作抗菌剂。