methyl α-aminodecanoate hydrochloride | 106590-43-6

• 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 α-aminodecanoate hydrochloride
• 英文别名: methyl 2-aminodecanoate hydrochloride；Methyl 2-aminodecanoate;hydrochloride
• CAS: 106590-43-6
• 化学式: C₁₁H₂₃NO₂*ClH
• 分子量: 237.77
• InChiKey: NOINBGGSHQEPAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl α-aminodecanoate hydrochloride 在 甲醇 、 sodium hydroxide 、 tributylcosanoyl ammonium sulphate 、 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 二氯甲烷 为溶剂， 反应 13.0h， 生成 α-tert-butoxycarbonyl-ω-hydroxybis
  参考文献：
  名称：

  Gibbons, William A.; Hughes, Richard A.; Charalambous, Mario, Liebigs Annalen der Chemie, 1990, # 12, p. 1175 - 1183

  摘要：

  DOI：
• 作为产物：
  描述：

  acetylamino-octyl-malonic acid diethyl ester 在 盐酸 、 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 methyl α-aminodecanoate hydrochloride
  参考文献：
  名称：

  Gibbons, William A.; Hughes, Richard A.; Charalambous, Mario, Liebigs Annalen der Chemie, 1990, # 12, p. 1175 - 1183

  摘要：

  DOI：

文献信息

• Nitrogen Alkylation of schiff bases and amidines as a route to N-alkyl amino acids
  作者：Martin J. O'Donnell、William A. Bruder、Byron W. Daugherty、Deshan Liu、Krzysztof Wojciechowski

  DOI：10.1016/0040-4039(84)80096-9

  日期：1984.1

  Schiff base and amidine ester 3 are alkylated and then hydrolyzed to yield N-alkyl amino acids 4 in 41–75% yield with high to complete retention of optical activity.

  将席夫碱和am酸酯3烷基化，然后水解，以41-75％的收率得到N-烷基氨基酸4，并具有完全保留的光学活性。
• A new type of chiral-pyridoxamines for catalytic asymmetric transamination of α-keto acids
  作者：Jianfeng Chen、Junyu Zhao、Xing Gong、Dongfang Xu、Baoguo Zhao

  DOI：10.1016/j.tetlet.2016.09.005

  日期：2016.10

  A new type of chiral pyridoxamines bearing an adjacent chiral stereocenter has been developed via multi-step synthesis. The pyridoxamines displayed catalytic activity in asymmetric transamination of α-keto acids to give a variety of optically active amino acids in 27–78% yields with 34–62% ee’s under very mild conditions. This work provides a synthetic strategy to construct new chiral pyridoxamines

  通过多步合成已经开发了一种新型的带有相邻手性立体中心的手性吡ido胺。吡ido胺在非常温和的条件下，在α-酮酸的不对称转氨反应中显示出催化活性，从而以27-78％的产率提供了34-62％ee的多种光学活性氨基酸。这项工作提供了使用溴吡啶7作为关键合成子来构建新的手性吡ido胺的合成策略，也代表了手性吡x胺在不对称催化中的早期应用实例。
• Lipidic peptides X. Synthesis, structural and physico-chemical elucidation of lipidic amino acid conjugates with hydrophilic compounds
  作者：Istvan Toth、Graeme J. Anderson、Rohanah Hussain、Ian P. Wood、Esther del Olmo Fernandez、Peter Ward、William A. Gibbons

  DOI：10.1016/s0040-4020(01)88194-1

  日期：——

  Lipidic amino acids 1a, c and dimer 1b were coupled to highly hydrophilic compounds, lactic, glycolic and gluconic acids and protected gulonic acid, yielding conjugates 1d,f,h,i,j,l and o. After carboxyl deprotection, acids e,g and m and were obtained. Physico-chemical investigations of these compounds were carried out using proton nuclear magnetic resonance. Plots of chemical shift versus concentration

  脂质氨基酸1a，c和二聚体1b与高度亲水的化合物，乳酸，乙醇酸和葡萄糖酸以及受保护的古洛糖酸偶联，得到缀合物1d，f，h，i，j，l和o。羧基脱保护后，得到酸e，g和m 1和m。使用质子核磁共振对这些化合物进行了物理化学研究。化学位移对浓度的图揭示了在高浓度下形成聚集体或胶束而在低浓度下形成单体。
• Hussain, Rohanah; Toth, Istvan; Gibbons, William A., Liebigs Annalen der Chemie, 1991, # 9, p. 963 - 966
  作者：Hussain, Rohanah、Toth, Istvan、Gibbons, William A.

  DOI：——

  日期：——
• Pro-apoptotic activity of lipidic α-amino acids isolated from Protopalythoa variabilis
  作者：Diego Veras Wilke、Paula Christine Jimenez、Renata Mendonça Araújo、Wildson Max Barbosa da Silva、Otília Deusdênia Loiola Pessoa、Edilberto Rocha Silveira、Claudia Pessoa、Manoel Odorico de Moraes、Mariusz Skwarczynski、Pavla Simerska、Istvan Toth、Letícia Veras Costa-Lotufo

  DOI：10.1016/j.bmc.2010.09.027

  日期：2010.11

  Lipidic alpha-amino acids (LAAs) have been described as non-natural amino acids with long saturated or unsaturated aliphatic chains. In the continuing prospect to discover anticancer agents from marine sources, we have obtained a mixture of two cytotoxic LAAs (1a and 1b) from the zoanthid Protopalythoa variabilis. The anti-proliferative potential of 14 synthetic LAAs and 1a/1b were evaluated on four tumor cell lines (HCT-8, SF-295, MDA-MB-435, and HL-60). Five of the synthetic LAAs showed high percentage of tumor cell inhibition, while 1a/1b completely inhibited tumor cell growth. Additionally, apoptotic effects of 1a/1b were studied on HL-60 cell line. 1a/1b-treated cells showed apoptosis morphology, loss of mitochondrial potential, and DNA fragmentation. (C) 2010 Elsevier Ltd. All rights reserved.