(E)-1-(2-(2-nitrovinyl)phenyl)pyrrolidine | 1028090-91-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (E)-1-(2-(2-nitrovinyl)phenyl)pyrrolidine
• 英文别名: 1-[2-(2-Nitroethenyl)phenyl]pyrrolidine；1-[2-[(E)-2-nitroethenyl]phenyl]pyrrolidine
• CAS: 1028090-91-6
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: BKBOHIWCOXIKAH-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-(2-nitrovinyl)phenyl)pyrrolidine 以 正丁醇 为溶剂， 反应 60.0h， 以20%的产率得到1-{2-[(Z)-2-nitrovinyl]phenyl}-pyrrolidine
  参考文献：
  名称：

  使用一些官能化 CH-酸和天然仲胺的 T 反应的范围和局限性

  摘要：

  研究了 T 反应的范围和局限性，重点是使用手性天然产物作为起始材料制备新型手性杂环，并通过提出的机制解释了新形成的立体中心的非对映选择性引入。

  DOI：

  10.3987/com-07-11260
• 作为产物：
  描述：

  硝基甲烷 、 2-(1-吡咯烷基)苯甲醛 在 potassium fluoride 、 盐酸二甲胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以59%的产率得到(E)-1-(2-(2-nitrovinyl)phenyl)pyrrolidine
  参考文献：
  名称：

  使用一些官能化 CH-酸和天然仲胺的 T 反应的范围和局限性

  摘要：

  研究了 T 反应的范围和局限性，重点是使用手性天然产物作为起始材料制备新型手性杂环，并通过提出的机制解释了新形成的立体中心的非对映选择性引入。

  DOI：

  10.3987/com-07-11260

文献信息

• 테트라하이드로퀴놀린 유도체의 제조방법
  申请人：Soonchunhyang University Industry Academy Cooperation Foundation 순천향대학교 산학협력단(220040359422) BRN ▼312-82-10071

  公开号：KR20190023193A

  公开（公告）日：2019-03-08

  본 발명은 테트라하이드로퀴놀린 유도체의 제조방법에 관한 것으로, 구체적으로 루이스 산을 이용하여 오쏘-다이알킬아미노 나이트로스틸렌 유도체의 분자내 고리화 반응, 구체적으로 분자내 1,5-수소전이/고리화 반응을 통해 테트라하이드로퀴놀린 유도체를 제조하는 것에 관한 것이다. 본 발명의 제조방법은 마일드한 온도 조건에서 높은 수율로 생물학적으로 중요한 테트라하이드로퀴놀린의 다양한 유도체를 제조할 수 있다.

  这项发明涉及四氢喹啉衍生物的制备方法，具体而言，通过使用路易斯酸促进内环化反应，具体而言是分子内1,5-氢迁移/环化反应，制备四氢喹啉衍生物。该发明的制备方法可以在温和的温度条件下高产率地制备生物学上重要的四氢喹啉的各种衍生物。
• Suppression of TRIF-dependent signaling pathway of toll-like receptors by (E)-1-(2-(2-nitrovinyl)phenyl)pyrrolidine
  作者：Gyo-Jeong Gu、Sang-Hoon Eom、Chang Won Suh、Kwang Oh Koh、Dae Young Kim、Hyung-Sun Youn

  DOI：10.1016/j.ejphar.2013.09.045

  日期：2013.12

  Toll-like receptors (TLRs) play an important role in the recognition of microbial pathogens and induce innate immune responses. The recognition of microbial components by TLRs triggers the activation of myeloid differential factor 88 (MyD88)- and toll-interleukin-1 receptor domain containing adapter inducing interferon-beta (TRIF)-dependent downstream signaling pathways. Previously, we synthesized (E)-1-(2-(2-nitrovinyl)phenyl)pyrrolidine (NVPP), which contains a nitrovinyl-phenyl and pyrrolidine. To evaluate the therapeutic potential of NVPP, its effect on signal transduction via the TRIF-dependent pathway of TLRs induced by lipopolysaccharide ([PS) or polyinosinic-polycytidylic acid (poly[I:C]) was examined. NVPP inhibited [PS or poly[I:C]-induced activation of nuclear factor-kappa B (NF-kappa B) and interferon regulatory factor 3 (IRF3), and the phosphorylalion of IRF3, as well as inhibiting the activation of interferon inducible genes such as interferon inducible protein-10 (IP-10). These results suggest that NVPP can modulate TRIP-dependent signaling pathways of TLRs, potentially resulting in effective therapeutics for chronic inflammatory diseases. (C) 2013 Elsevier B.V. All rights reserved.
• Focused structure-activity relationship profiling around the 2-phenylindole scaffold of a cannabinoid type-1 receptor agonist-positive allosteric modulator: site-III aromatic-ring congeners with enhanced activity and solubility
  作者：Peter C. Schaffer、Pushkar M. Kulkarni、David R. Janero、Ganesh A. Thakur

  DOI：10.1016/j.bmc.2020.115727

  日期：2020.11

  Specific tuning of cannabinoid 1 receptor (CB1R) activity by small-molecule allosteric modulators is a therapeutic modality with multiple properties inherently advantageous to therapeutic applications. We previously generated a library of unique CB1R positive allosteric modulators (PAMs) derived from GAT211, which has three pharmacophoric sites critical to its ago-PAM activity. To elaborate our CB1R PAM library, we report the rational design and molecular-pharmacology profiling of several 2-phenylindole analogs modified at the "site-III" aromatic ring. The comprehensive structure-activity relationship (SAR) investigation demonstrates that attaching small lipophilic functional groups on the ortho-position of the GAT211 site-III phenyl ring could markedly enhance CB1R ago-PAM activity. Select site-III modifications also improved GAT211's water solubility. The SAR reported both extends the structural diversity of this compound class and demonstrates the utility of GAT211's site-III for improving the parent compound's drug-like properties of potency and/or aqueous solubility.
• Scope and Limitations of the T-Reaction Employing Some Functionalized C-H-Acids and Naturally Occurring Secondary Amines
  作者：Constantin Rabong、Christian Hametner、Kurt Mereiter、Victor G. Kartsev、Ulrich Jordis

  DOI：10.3987/com-07-11260

  日期：——

  Scope and limitations of the T-reaction with emphasis on using chiral, natural products as starting materials to prepare novel chiral heterocycles is studied and the diastereoselective introduction of newly formed stereocenters is explained via proposed mechanisms.

  研究了 T 反应的范围和局限性，重点是使用手性天然产物作为起始材料制备新型手性杂环，并通过提出的机制解释了新形成的立体中心的非对映选择性引入。