ethyl 2-(cycloheptylamino)-2-oxoacetate | 349119-51-3

• 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: ethyl 2-(cycloheptylamino)-2-oxoacetate
• 英文别名: Ethyl (cycloheptylamino)(oxo)acetate
• CAS: 349119-51-3
• 化学式: C₁₁H₁₉NO₃
• mdl: MFCD02859915
• 分子量: 213.277
• InChiKey: WKRCGJWGUDSIHW-UHFFFAOYSA-N

物化性质

• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  ethyl 2-(cycloheptylamino)-2-oxoacetate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以79%的产率得到potassium 2-(cycloheptylamino)-2-oxoacetate
  参考文献：
  名称：

  含氮杂环的直接CH氨基甲酰化

  摘要：

  在固有的亲电C（sp 2）中心的亲核自由基加成非常适合杂环的直接功能化。使用长凳稳定的和可商购的草酸烷基酯和草酰胺酸衍生物与光氧化还原催化结合，报道了杂环的直接氨基甲酰基化在单个步骤中产生酰胺官能化的药效基团。报道的反应条件与药学上感兴趣的结构复杂的杂环底物相容。值得注意的是，发现含有与标准酰胺化反应不相容的官能团的衍生物，例如羧酸和未保护的胺，适用于该反应范式。

  DOI：

  10.1002/chem.201806159
• 作为产物：
  描述：

  环庚胺 、 草酰氯单乙酯 生成 ethyl 2-(cycloheptylamino)-2-oxoacetate
  参考文献：
  名称：

  可见光介导的氨基甲酰基向杂芳烃的加成†

  摘要：

  氨基甲酰基自由基的产生，然后将它们加到杂芳烃中，是在温和的条件下通过无金属的草酸的光催化脱羧反应进行的。该方法已被用于使用α-氨基酸衍生的草酰胺酸对杂芳族碱进行氨基甲酰基化，从而得到相应的酰胺而没有外消旋化作用。

  DOI：

  10.1039/c8cc08326f

文献信息

• Discovery of Cytochrome P450 4F11 Activated Inhibitors of Stearoyl Coenzyme A Desaturase
  作者：Sarah E. Winterton、Emanuela Capota、Xiaoyu Wang、Hong Chen、Prema L. Mallipeddi、Noelle S. Williams、Bruce A. Posner、Deepak Nijhawan、Joseph M. Ready

  DOI：10.1021/acs.jmedchem.8b00052

  日期：2018.6.28

  Stearoyl-CoA desaturase (SCD) catalyzes the first step in the conversion of saturated fatty acids to unsaturated fatty acids. Unsaturated fatty acids are required for membrane integrity and for cell proliferation. For these reasons, inhibitors of SCD represent potential treatments for cancer. However, systemically active SCD inhibitors result in skin toxicity, which presents an obstacle to their development

  硬脂酰辅酶A去饱和酶（SCD）催化饱和脂肪酸向不饱和脂肪酸转化的第一步。膜完整性和细胞增殖需要不饱和脂肪酸。由于这些原因，SCD抑制剂代表了潜在的癌症治疗方法。但是，具有内在活性的SCD抑制剂会导致皮肤毒性，这对它们的发展构成了障碍。我们最近描述了一系列草酸二酰胺，它们通过CYP4F11介导的代谢转化为癌症子集内的活性SCD抑制剂。在本文中，我们描述了草酸二酰胺和相关N-酰基脲的优化，以及与代谢活化和SCD抑制有关的结构-活性关系的分析。
• Visible-light mediated carbamoyl radical addition to heteroarenes
  作者：Ashique Hussain Jatoi、Govind Goroba Pawar、Frédéric Robert、Yannick Landais

  DOI：10.1039/c8cc08326f

  日期：——

  The generation of carbamoyl radicals, followed by their addition to heteroarenes, was performed under mild conditions through a metal-free photocatalyzed decarboxylation of oxamic acids. The process has been applied to the carbamoylation of heteroaromatic bases using α-aminoacid-derived oxamic acids, leading to the corresponding amides without racemization.

  氨基甲酰基自由基的产生，然后将它们加到杂芳烃中，是在温和的条件下通过无金属的草酸的光催化脱羧反应进行的。该方法已被用于使用α-氨基酸衍生的草酰胺酸对杂芳族碱进行氨基甲酰基化，从而得到相应的酰胺而没有外消旋化作用。
• Design, Synthesis, and Antiviral Activity of Entry Inhibitors That Target the CD4-Binding Site of HIV-1
  作者：Francesca Curreli、Spreeha Choudhury、Ilya Pyatkin、Victor P. Zagorodnikov、Anna Khulianova Bulay、Andrea Altieri、Young Do Kwon、Peter D. Kwong、Asim K. Debnath

  DOI：10.1021/jm3002247

  日期：2012.5.24

  The CD4 binding site on HIV-1 gp120 has been validated as a drug target to prevent HIV-1 entry to cells. Previously, we identified two small molecule inhibitors consisting of a 2,2,6,6-tetramethylpiperidine ring linked by an oxalamide to a p-halide-substituted phenyl group, which target this site, specifically, a cavity termed "Phe43 cavity". Here we use synthetic chemistry, functional assessment, and structure-based analysis to explore variants of each region of these inhibitors for improved antiviral properties. Alterations of the phenyl group and of the oxalamide linker indicated that these regions were close to optimal in the original lead compounds. Design of a series of compounds, where the tetramethylpiperidine ring was replaced with new scaffolds, led to improved antiviral activity. These new scaffolds provide insight into the surface chemistry at the entrance of the cavity and offer additional opportunities by which to optimize further these potential-next-generation therapeutics and microbicides against HIV-1.
• Direct C−H Carbamoylation of Nitrogen-Containing Heterocycles
  作者：Matthieu Jouffroy、Jongrock Kong

  DOI：10.1002/chem.201806159

  日期：2019.2.11

  additions at innately electrophilic C(sp2) centers are perfectly suited for the direct functionalization of heterocycles. Using bench stable and commercially available alkyl oxamate and oxamic acid derivatives in combination with photoredox catalysis, a direct carbamoylation of heterocycles yielding amide functionalized pharmacophores in a single step is reported. The reaction conditions reported are

  在固有的亲电C（sp 2）中心的亲核自由基加成非常适合杂环的直接功能化。使用长凳稳定的和可商购的草酸烷基酯和草酰胺酸衍生物与光氧化还原催化结合，报道了杂环的直接氨基甲酰基化在单个步骤中产生酰胺官能化的药效基团。报道的反应条件与药学上感兴趣的结构复杂的杂环底物相容。值得注意的是，发现含有与标准酰胺化反应不相容的官能团的衍生物，例如羧酸和未保护的胺，适用于该反应范式。