(E)-1-(imidazolyl)-2-(ethoxycarbonyl)ethane | 211099-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-1-(imidazolyl)-2-(ethoxycarbonyl)ethane
• 英文别名: ethyl (E)-3-(imidazol-1-yl)-propenoate；(E)-ethyl 3-(1H-imidazol-1-yl)acrylate；ethyl (E)-3-imidazol-1-ylprop-2-enoate
• CAS: 211099-03-5
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: PFBNSWWZXGYJSV-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  咪唑 、 ethyl (E)-3-iodopropenoate 在 三乙烯二胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以96%的产率得到(E)-1-(imidazolyl)-2-(ethoxycarbonyl)ethane
  参考文献：
  名称：

  碱介导的芳氧基和氨基取代丙烯酸乙酯的立体定向合成

  摘要：

  芳氧基和氨基取代的E-和Z-乙基-3-丙烯酸酯的立体定向合成因其在聚合物工业和药物化学中的潜力而受到关注。在铜催化 ( E )- 和 ( Z )-3-碘代丙烯酸乙酯与苯酚和N-杂环的交叉偶联反应过程中，我们发现了一种非常简单的（非金属）方法用于芳氧基和氨基取代的立体定向合成丙烯酸酯。为了研究芳氧基和氨基取代的丙烯酸酯的立体选择性这个长期存在的问题，一系列O-和N-取代的亲核试剂被允许与( E )-和( Z )-3-碘代丙烯酸乙酯反应。不同碱的筛选表明，DABCO（1,4-二氮杂双环[2.2.2]辛烷）以立体有择方式成功地将( E )-和( Z )-3-碘代丙烯酸乙酯转化为芳氧基和氨基取代的丙烯酸乙酯。本文详细介绍了这种 DABCO 介导的芳氧基和氨基取代的E-或Z-丙烯酸酯的立体定向合成。

  DOI：

  10.1021/jo201948e

文献信息

• Green H2O-Promoted Solvent-Free Synthesis of Enaminocarbonyl Compounds with High Stereoselectivity from Electron-Deficient Terminal Alkynes
  作者：Xiao Yun Chen、Luming Zhang、Yaonan Tang、Shuxia Yuan、Baocheng Zhu、Guang Chen、Xiaofang Cheng

  DOI：10.1055/s-0040-1707968

  日期：2020.6

  A green H2O-promoted solvent-free hydroamination of electron-deficient terminal alkynes with amines has been developed. All secondary amines, including aliphatic and aromatic amines, gave the corresponding (E)-enamines in good to excellent yields, whereas primary aromatic amines afforded Z-configured products in moderate yields. Propiolates, propyn-1-ones, propynamides, and 1-(ethynylsulfonyl)-4-methylbenzene

  已开发出一种绿色 H2O 促进的缺电子末端炔烃与胺的无溶剂加氢胺化。所有仲胺，包括脂肪族和芳族胺，都以良好到极好的产率得到相应的 (E)-烯胺，而伯芳胺以中等产率提供 Z-构型的产物。在此迈克尔加成中探索了丙炔酸酯、丙炔-1-酮、丙炔酰胺和 1-（乙炔基磺酰基）-4-甲基苯。
• Phosphine-Catalyzed Vinylation at Low Acetylene Pressure
  作者：Nikolai A. Sitte、Maximilian Menche、Pavel Tužina、Frank Bienewald、Ansgar Schäfer、Peter Comba、Frank Rominger、A. Stephen K. Hashmi、Thomas Schaub

  DOI：10.1021/acs.joc.1c01807

  日期：2021.9.17

  The vinylation of various nucleophiles with acetylene at a maximum pressure of 1.5 bar is achieved by organocatalysis with easily accessible phosphines like tri-n-butylphosphine. A detailed mechanistic investigation by quantum-chemical and experimental methods supports a nucleophilic activation of acetylene by the phosphine catalyst. At 140 °C and typically 5 mol % catalyst loading, cyclic amides,

  与乙炔各种亲核试剂在1.5巴的最大压力的乙烯化是通过用有机催化方便膦等三-实现ñ丁基膦。通过量子化学和实验方法进行的详细机理研究支持膦催化剂对乙炔的亲核活化。在 140 °C 和通常 5 mol% 催化剂负载下，环酰胺、恶唑烷酮、脲、不饱和环胺和醇成功乙烯基化。此外，乙烯基鏻物种的原位生成也可用于醛的 Wittig 型官能化。
• NUCLEAR TRANSPORT MODULATORS AND USES THEREOF
  申请人：Shacham Sharon

  公开号：US20110275607A1

  公开（公告）日：2011-11-10

  The invention generally relates to the field of nuclear transport modulators, e.g., CRM1 inhibitors, and more particularly to new substituted-heterocyclic azole compounds, the synthesis and use of these compounds and their pharmaceutical compositions, e.g., in the treatment, modulation and/or prevention of physiological conditions associated with CRM1 activity such as in treating cancer and other neoplastic disorders, inflammatory diseases, disorders of abnormal tissue growth and fibrosis including cardiomyopathy, pulmonary fibrosis, hepatic fibrosis, glomerulonephritis, and other renal disorders, and for the treatment of viral infections (both acute and chronic).

  本发明通常涉及核运输调节剂领域，例如CRM1抑制剂，更具体地涉及新的取代杂环唑类化合物，这些化合物的合成和使用以及它们的制药组合物，例如在治疗、调节和/或预防与CRM1活性相关的生理状况方面的用途，例如治疗癌症和其他肿瘤性疾病、炎症性疾病、异常组织生长和纤维化疾病，包括心肌病、肺纤维化、肝纤维化、肾小球肾炎和其他肾脏疾病，以及治疗病毒感染（急性和慢性）。
• Inhibition of the CRM1-mediated nucleocytoplasmic transport by N-azolylacrylates: Structure–activity relationship and mechanism of action
  作者：Tine Van Neck、Christophe Pannecouque、Els Vanstreels、Miguel Stevens、Wim Dehaen、Dirk Daelemans

  DOI：10.1016/j.bmc.2008.09.051

  日期：2008.11

  CRM1-mediated nucleocytoplasmic transport plays an important role in many cellular processes and diseases. To investigate the structural basis required for the inhibition of the CRM1-mediated nuclear export we have synthesized analogs of a previously identified small molecule lead compound and monitored their activity against the Rev function of the human immunodeficiency virus. Microscopy studies show that the active congeners of this series inhibit the nucleocytoplasmic transport of Rev and the co-localization between Rev and CRM1 in living cells. Mechanism of action studies show their interaction with the Cys528 residue of CRM1 involving a Michael-addition type of reaction. However, structure-activity relationship demonstrates strict constraints to the structure of the inhibitors, and shows that activity is not solely correlated to Michael-addition suggesting a more complex mechanism of action. Our results are suggestive for the existence of a well-defined interaction at the CRM1-NES binding site. In addition, the most selective congener inhibited the HIV-1 production in latently infected cells. These specific CRM1 inhibitors are of interest as tool for analyzing the mechanisms of post-transcriptional control of gene expression and provide insight in the design of new agents. (C) 2008 Elsevier Ltd. All rights reserved.
• US8513230B2
  申请人：——

  公开号：US8513230B2

  公开（公告）日：2013-08-20