methyl 3-((2-(methoxycarbonyl)ethyl)amino)propanoate hydrochloride | 67363-88-6

• 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 3-((2-(methoxycarbonyl)ethyl)amino)propanoate hydrochloride
• 英文别名: dimethyl β,β'-imidinodipropionate hydrochloride；3,3'-iminobis(methyl propionate) hydrochloride；dimethyl iminodipropionate hydrochloride；3,3'-imino-di-propionic acid dimethyl ester; hydrochloride；3,3'-Imino-di-propionsaeure-dimethylester; Hydrochlorid；Methyl 3-[(3-methoxy-3-oxopropyl)amino]propanoate hydrochloride；methyl 3-[(3-methoxy-3-oxopropyl)amino]propanoate;hydrochloride
• CAS: 67363-88-6
• 化学式: C₈H₁₅NO₄*ClH
• 分子量: 225.672
• InChiKey: XFYOAIAPAOULRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.12
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  64.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-((2-(methoxycarbonyl)ethyl)amino)propanoate hydrochloride 在 sodium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 107.5h， 生成 N-(7-methylpyridino[3,2-e]pyridin-2-yl)-3-((2-(N-(2-quinolyl)carbamoyl)ethyl)amino)propanamide hydrochloride
  参考文献：
  名称：

  Recognition of Guanine−Guanine Mismatches by the Dimeric Form of 2-Amino-1,8-naphthyridine

  摘要：

  Dimeric 2-amino-1,8-naphthyridine selectively binds to a G-G mismatch with hi-h affinity (K-d = 53 nM). We have investigated a binding mechanism of naphthyridine dimer 2 to a G-G mismatch by spectroscopic studies, thermodynamic analysis, and structure-activity studies for the thermal stabilization of the mismatch. H-1 NMR spectra of a complex of 2 with 9-mer duplex d(CATCGGATG)(2) containing a G-G mismatch showed that all hydrogens in two naphthyridine rings of 2 were observed upfield compared to those C of 2 in a free state. The 2D-NOESY experiments showed that each naphthyridine of 2 binds to a guanine in the, G-G mismatch within the pi -stack. In CD spectra, a large conformational change of the G-G mismatch-containing duplex was observed upon complex formation with 2. Isothermal calorimetry titration of 2 binding to the G-G mismatch showed that the stoichiometry for the binding is about 1:1 and that the binding is enthalpy-controlled. It is clarified by structure-activity studies that show (i) the linker connecting two naphthyridine rings was essential for the stabilization of the G-G mismatch, (ii) the binding efficiency was very sensitive to the linker structure, and (iii) the binding of two naphthyridines to each one of two Gs in the G-G pi -dsmatch is essential for a strong stabilization. These results strongly supported the intercalation of both naphthyridine rings of 2 into DNA base pairs and the formation of a hydrogen bonded complex with the G-G mismatch.

  DOI：

  10.1021/ja0109186
• 作为产物：
  描述：

  甲醇 、 双(2-氰基乙基)胺 在 氯化亚砜 作用下， 以16.27 g的产率得到methyl 3-((2-(methoxycarbonyl)ethyl)amino)propanoate hydrochloride
  参考文献：
  名称：

  Synthesis and physicochemical properties of chelating sorbents containing functional groups of N-aryl-3-aminopropionic acids

  摘要：

  合成了两种不同类型的螯合吸附剂，它们在聚合物基质中引入了亚氨基二丙酸基团：一种是基于线性聚苯乙烯的羧乙基氨基聚苯乙烯（吸附剂1），另一种是基于苯乙烯和二乙烯基苯共聚物的羧乙基氨基甲基聚苯乙烯（吸附剂2）。测定了吸附剂的功能基团的电离常数和浓度（对氢离子的交换容量）。这些吸附剂对铜(II)离子表现出高选择性，从氨-醋酸盐缓冲溶液中吸附铜(II)离子的最大值位于pH 5.0–7.5范围内。对于连续搅拌的铜(II)溶液与吸附剂系统，达到交换平衡所需的时间分别为3.5小时和2小时（吸附剂1和吸附剂2）。对铜(II)离子的交换容量分别为2.54和0.10 mmol g^-1。

  DOI：

  10.1007/s11172-006-0339-3

文献信息

• Oxidative N-nitration of secondary amines
  作者：O. V. Anikin、G. V. Pokhvisneva、D. L. Lipilin、A. V. Mezhenin、V. A. Tartakovsky

  DOI：10.1007/s11172-009-0280-3

  日期：2009.10

  Reaction of secondary amines with the nitrite anion assisted by diacetoxyiodobenzene results in respective N-nitroamines. It is the first example of oxidative nitration of the amino group. N-Nitrosoamines are by-products. The yields and the ratio of the nitration and nitrosation products depend on the nature of the starting amine, cation of the salt used, and the solvent.

  二乙酰氧基碘苯协助亚硝酸根与仲胺反应，生成相应的N-亚硝基胺。这是首次报道的氨基的氧化亚硝化反应。N-亚硝胺是副产物。亚硝化和亚硝基化产物的产率和比例取决于起始胺的性质、所用盐的阳离子及溶剂。
• Ashton, Peter R.; Boyd, Sue E.; Brown, Christopher L., Chemistry - A European Journal, 1996, vol. 2, # 9, p. 1115 - 1128
  作者：Ashton, Peter R.、Boyd, Sue E.、Brown, Christopher L.、Jayaraman, Narayanaswamy、Nepogodiev, Sergey A.、Stoddart, J. Fraser

  DOI：——

  日期：——
• Synthesis and physicochemical properties of chelating sorbents containing functional groups of N-aryl-3-aminopropionic acids
  作者：L. K. Neudachina、Yu. G. Yatluk、N. V. Baranova、A. V. Pestov、A. A. Vshivkov、A. Yu. Plekhanova、M. V. Zorina

  DOI：10.1007/s11172-006-0339-3

  日期：2006.5

  Two types of chelating sorbents with different types of addition of iminodipropionate groups to a polymeric matrix were synthesized: carboxyethylated aminopolystyrene (sorbent 1) based on linear polystyrene and carboxyethylaminomethylpolystyrene (sorbent 2) based on the copolymer of styrene and divinylbenzene. The ionization constants and concentrations of functional groups of the sorbents (exchange capacity for hydrogen ions) were determined. The sorbents exhibit high selectivity for copper(II) ions with the maximum of sorption from ammonia—acetate buffer solutions lying in a range of pH 5.0–7.5. The time needed for a solution of copper(II)—sorbent system with continuous stirring to reach exchange equilibrium is 3.5 and 2 h for sorbents 1 and 2, respectively. The exchange capacity for copper(II) ions is 2.54 and 0.10 mmol g−1, respectively.

  合成了两种不同类型的螯合吸附剂，它们在聚合物基质中引入了亚氨基二丙酸基团：一种是基于线性聚苯乙烯的羧乙基氨基聚苯乙烯（吸附剂1），另一种是基于苯乙烯和二乙烯基苯共聚物的羧乙基氨基甲基聚苯乙烯（吸附剂2）。测定了吸附剂的功能基团的电离常数和浓度（对氢离子的交换容量）。这些吸附剂对铜(II)离子表现出高选择性，从氨-醋酸盐缓冲溶液中吸附铜(II)离子的最大值位于pH 5.0–7.5范围内。对于连续搅拌的铜(II)溶液与吸附剂系统，达到交换平衡所需的时间分别为3.5小时和2小时（吸附剂1和吸附剂2）。对铜(II)离子的交换容量分别为2.54和0.10 mmol g^-1。
• Recognition of Guanine−Guanine Mismatches by the Dimeric Form of 2-Amino-1,8-naphthyridine
  作者：Kazuhiko Nakatani、Shinsuke Sando、Hiroyuki Kumasawa、Jun Kikuchi、Isao Saito

  DOI：10.1021/ja0109186

  日期：2001.12.19

  Dimeric 2-amino-1,8-naphthyridine selectively binds to a G-G mismatch with hi-h affinity (K-d = 53 nM). We have investigated a binding mechanism of naphthyridine dimer 2 to a G-G mismatch by spectroscopic studies, thermodynamic analysis, and structure-activity studies for the thermal stabilization of the mismatch. H-1 NMR spectra of a complex of 2 with 9-mer duplex d(CATCGGATG)(2) containing a G-G mismatch showed that all hydrogens in two naphthyridine rings of 2 were observed upfield compared to those C of 2 in a free state. The 2D-NOESY experiments showed that each naphthyridine of 2 binds to a guanine in the, G-G mismatch within the pi -stack. In CD spectra, a large conformational change of the G-G mismatch-containing duplex was observed upon complex formation with 2. Isothermal calorimetry titration of 2 binding to the G-G mismatch showed that the stoichiometry for the binding is about 1:1 and that the binding is enthalpy-controlled. It is clarified by structure-activity studies that show (i) the linker connecting two naphthyridine rings was essential for the stabilization of the G-G mismatch, (ii) the binding efficiency was very sensitive to the linker structure, and (iii) the binding of two naphthyridines to each one of two Gs in the G-G pi -dsmatch is essential for a strong stabilization. These results strongly supported the intercalation of both naphthyridine rings of 2 into DNA base pairs and the formation of a hydrogen bonded complex with the G-G mismatch.