Ethyl 2-[2-(cyclohexen-1-yl)ethylamino]cyclohexene-1-carboxylate | 1061735-70-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酰胺
• 英文名称: Ethyl 2-[2-(cyclohexen-1-yl)ethylamino]cyclohexene-1-carboxylate
• 英文别名: ethyl 2-[2-(cyclohexen-1-yl)ethylamino]cyclohexene-1-carboxylate
• CAS: 1061735-70-3
• 化学式: C₁₇H₂₇NO₂
• 分子量: 277.407
• InChiKey: WZRZBVQHVDQVRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[2-(cyclohexen-1-yl)ethylamino]cyclohexene-1-carboxylate 、 衣康酸酐 以 氯仿 为溶剂， 以1.12 g的产率得到
  参考文献：
  名称：

  通过 Prins 环化、Au 催化的烯炔环异构化和自动酰胺合成实现四个不同杂环文库的组装

  摘要：

  我们描述了有效组装四个新杂环库的统一合成策略。合成开始于创建一系列结构不同的吡咯烷酮或哌啶酮。此类化合物是从容易获得的胺、酮酯和不饱和酸酐开始的简单单瓶操作中获得的。使用由我们的 Prins 环化方案快速组装的含四氢吡喃的酮酯，能够有效地融合吡喃和哌啶酮核心。新开发的 Au(I) 催化的含炔烯酰胺的环异构化通过提供快速进入广泛的双环和三环二酰胺进一步扩展了杂环的多样性。

  DOI：

  10.1021/jo301061r
• 作为产物：
  描述：

  2-环己酮甲酸乙酯 、 2-(1-环己烯基)乙胺 以 氯仿 为溶剂， 生成 Ethyl 2-[2-(cyclohexen-1-yl)ethylamino]cyclohexene-1-carboxylate
  参考文献：
  名称：

  通过 Prins 环化、Au 催化的烯炔环异构化和自动酰胺合成实现四个不同杂环文库的组装

  摘要：

  我们描述了有效组装四个新杂环库的统一合成策略。合成开始于创建一系列结构不同的吡咯烷酮或哌啶酮。此类化合物是从容易获得的胺、酮酯和不饱和酸酐开始的简单单瓶操作中获得的。使用由我们的 Prins 环化方案快速组装的含四氢吡喃的酮酯，能够有效地融合吡喃和哌啶酮核心。新开发的 Au(I) 催化的含炔烯酰胺的环异构化通过提供快速进入广泛的双环和三环二酰胺进一步扩展了杂环的多样性。

  DOI：

  10.1021/jo301061r

文献信息

• A Pairwise Chemical Genetic Screen Identifies New Inhibitors of Glucose Transport
  作者：Olesya A. Ulanovskaya、Jiayue Cui、Stephen J. Kron、Sergey A. Kozmin

  DOI：10.1016/j.chembiol.2010.12.015

  日期：2011.2

  Oxidative phosphorylation (OXPHOS) and glycolysis are the two main pathways that control energy metabolism of a cell. The Warburg effect, in which glycolysis remains active even under aerobic conditions, is considered a key driver for cancer cell proliferation, malignancy, metastasis, and therapeutic resistance. To target aerobic glycolysis, we exploited the complementary roles of OXPHOS and glycolysis in ATP synthesis as the basis for a chemical genetic screen, enabling rapid identification of novel small-molecule inhibitors of facilitative glucose transport. Blocking mitochondrial electron transport with antimycin A or leucascandrolide A had little effect on highly glycolytic A549 lung carcinoma cells, but adding known glycolytic inhibitors 2-deoxy-D-glucose, iodoacetate or cytochalasin B, rapidly depleted intracellular ATP, displaying chemical synthetic lethality. Based on this principle, we exposed antimycin A-treated A549 cells to a newly synthesized 955 member diverse scaffold small-molecule library, screening for compounds that rapidly depleted ATP levels. Two compounds potently suppressed ATP synthesis, induced G1 cell-cycle arrest and inhibited lactate production. Pathway analysis revealed that these novel probes inhibited GLUT family of facilitative transmembrane transporters but, unlike cytochalasin B, had no effect on the actin cytoskeleton. Our work illustrated the utility of a pairwise chemical genetic screen for discovery of novel chemical probes, which would be useful not only to study the system-level organization of energy metabolism but could also facilitate development of drugs targeting upregulation of aerobic glycolysis in cancer.
• Assembly of Four Diverse Heterocyclic Libraries Enabled by Prins Cyclization, Au-Catalyzed Enyne Cycloisomerization, and Automated Amide Synthesis
  作者：Jiayue Cui、David I. Chai、Christopher Miller、Jason Hao、Christopher Thomas、JingQi Wang、Karl A. Scheidt、Sergey A. Kozmin

  DOI：10.1021/jo301061r

  日期：2012.9.7

  simple one-flask operation starting with readily available amines, ketoesters, and unsaturated anhydrides. The use of tetrahydropyran-containing ketoesters, which were rapidly assembled by our Prins cyclization protocol, enabled efficient fusion of pyran and piperidinone cores. A newly developed Au(I)-catalyzed cycloisomerization of alkyne-containing enamides further expanded heterocyclic diversity by

  我们描述了有效组装四个新杂环库的统一合成策略。合成开始于创建一系列结构不同的吡咯烷酮或哌啶酮。此类化合物是从容易获得的胺、酮酯和不饱和酸酐开始的简单单瓶操作中获得的。使用由我们的 Prins 环化方案快速组装的含四氢吡喃的酮酯，能够有效地融合吡喃和哌啶酮核心。新开发的 Au(I) 催化的含炔烯酰胺的环异构化通过提供快速进入广泛的双环和三环二酰胺进一步扩展了杂环的多样性。