(E)-3-环戊基丙烯醛 | 118235-51-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (E)-3-环戊基丙烯醛
• 中文别名: (2E)-3-环戊基丙烯醛
• 英文名称: (E)-3-cyclopentylacrylaldehyde
• 英文别名: 2-Propenal, 3-cyclopentyl-, (2E)-；(E)-3-cyclopentylprop-2-enal
• CAS: 118235-51-1
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: STNAQNGWDXASLM-ZZXKWVIFSA-N

物化性质

• 沸点：
  198.4±9.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-环戊基丙烯醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 3-cyclopentylprop-2-en-1-ol
  参考文献：
  名称：

  Novel Terminal Bipheny-Based Diapophytoene Desaturases (CrtN) Inhibitors as Anti-MRSA/VISR/LRSA Agents with Reduced hERG Activity

  摘要：

  CrtN has been identified as an attractive and druggable target for treating pigmented Staphylococcus aureus infections. More than 100 new compounds were synthesized, which target the overwhelming the defects of the CrtN inhibitor 1. Analogues 23a and 23b demonstrated a significant activity against pigmented S. aureus Newman and 13 MRSA strains (IC50 = 0.02-10.5 nM), along with lower hERG inhibition (IC50 > 30 mu M, similar to 10-fold decrease in comparison with 1). Furthermore, 23a and 23b were confirmed to reduce the staphylococcal load in the kidney and heart in a mouse model with normal treatment deeper than pretreatment ones, comparable even with vancomycin and linezolid. Remarkably, 23a could strongly block the pigment biosynthesis of these nine multidrug-resistant MRSA strains, including excellent activity against LRSA strains and VISA strains in vivo, and all of which demonstrated that 23a has a huge potential against intractable MRSA, VISA, and LRSA issues as a therapeutic drug.

  DOI：

  10.1021/acs.jmedchem.7b01300
• 作为产物：
  描述：

  环戊基甲醛 在 二异丁基氢化铝 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 (E)-3-环戊基丙烯醛
  参考文献：
  名称：

  N-苄氧基丙烯酰胺作为有机催化的 Domino aza-Michael/Morita-Baylis-Hillman 序列中的双亲核试剂

  摘要：

  我们在此描述了容易获得的丙烯酰胺和α,β-不饱和羰基之间的立体选择性有机催化的氮杂-迈克尔/森田-贝利斯-希尔曼多米诺骨牌反应。这种新颖的、PPh 3促进的原子经济一锅法具有中等至良好的产率和良好的立体选择性，导致具有环外烯键的各种取代的哌啶-2-酮，这被证明是进一步化学多样化的优异锚定。

  DOI：

  10.1021/acs.orglett.4c00295

文献信息

• [EN] HETEROCYCLIC AMIDES AS KINASE INHIBITORS<br/>[FR] AMIDES HÉTÉROCYCLIQUES UTILISÉS EN TANT QU'INHIBITEURS DE KINASE
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2016185423A1

  公开（公告）日：2016-11-24

  Disclosed are compounds having the formula: (I) wherein R1, R2, and R3 are as defined herein, and methods of making and using the same.

  揭示的是具有以下式的化合物：(I) 其中R1、R2和R3如本文所定义，并且制备和使用这些化合物的方法。
• Discovery and Lead-Optimization of 4,5-Dihydropyrazoles as Mono-Kinase Selective, Orally Bioavailable and Efficacious Inhibitors of Receptor Interacting Protein 1 (RIP1) Kinase
  作者：Philip A. Harris、Nicolas Faucher、Nicolas George、Patrick M. Eidam、Bryan W. King、Gemma V. White、Niall A. Anderson、Deepak Bandyopadhyay、Allison M. Beal、Veronique Beneton、Scott B. Berger、Nino Campobasso、Sebastien Campos、Carol A. Capriotti、Julie A. Cox、Alain Daugan、Frederic Donche、Marie-Hélène Fouchet、Joshua N. Finger、Brad Geddes、Peter J. Gough、Pascal Grondin、Bonnie L. Hoffman、Sandra J. Hoffman、Susan E. Hutchinson、Jae U. Jeong、Emilie Jigorel、Pauline Lamoureux、Lara K. Leister、John D. Lich、Mukesh K. Mahajan、Jamel Meslamani、Julie E. Mosley、Rakesh Nagilla、Pamela M. Nassau、Sze-Ling Ng、Michael T. Ouellette、Kishore K. Pasikanti、Florent Potvain、Michael A. Reilly、Elizabeth J. Rivera、Stéphane Sautet、Michelle C. Schaeffer、Clark A. Sehon、Helen Sun、James H. Thorpe、Rachel D. Totoritis、Paris Ward、Natalie Wellaway、David D. Wisnoski、James M. Woolven、John Bertin、Robert W. Marquis

  DOI：10.1021/acs.jmedchem.9b00318

  日期：2019.5.23

  RIP1 kinase inhibitors starting from a high-throughput screen and the lead-optimization of this series from a lead with minimal rat oral exposure to the identification of dihydropyrazole 77 with good pharmacokinetic profiles in multiple species. Additionally, we identified a potent murine RIP1 kinase inhibitor 76 as a valuable in vivo tool molecule suitable for evaluating the role of RIP1 kinase in chronic

  RIP1激酶调节坏死病和炎症，并可能在促成多种人类疾病（包括炎症和神经疾病）中发挥重要作用。目前，RIP1激酶抑制剂已进入早期临床试验，以评估炎性疾病（如牛皮癣，类风湿性关节炎和溃疡性结肠炎）以及神经系统疾病（如肌萎缩性侧索硬化症和阿尔茨海默氏病）。在本文中，我们从高通量筛选开始，研究了有效和高度选择性的二氢吡唑（DHP）RIP1激酶抑制剂的设计，并从具有最小大鼠口服暴露量的铅中对该系列的铅进行了优化，以鉴定二氢吡唑77在多个物种中具有良好的药代动力学特征。此外，我们确定了一种强效的鼠RIP1激酶抑制剂76作为一种有价值的体内工具分子，适用于评估RIP1激酶在慢性疾病模型中的作用。DHP 76在多发性硬化症和人类视网膜色素变性的小鼠模型中均显示出功效。
• Enantioselective Synthesis of Janus Kinase Inhibitor INCB018424 via an Organocatalytic Aza-Michael Reaction
  作者：Qiyan Lin、David Meloni、Yongchun Pan、Michael Xia、James Rodgers、Stacey Shepard、Mei Li、Laurine Galya、Brian Metcalf、Tai-Yuen Yue、Pingli Liu、Jiacheng Zhou

  DOI：10.1021/ol900350k

  日期：2009.5.7

  An enantioselective synthesis of INCB018424 via organocatalytic asymmetric aza-Michael addition of pyrazoles (16 or 20) to (E)-3-cyclopentylacrylaldehyde (23) using diarylprolinol silyl ether as the catalyst was developed. Michael adducts (R)-24 and (R)-27 were isolated in good yield and high ee and were readily converted to INCB018424.

  使用二芳基脯氨醇甲硅烷基醚作为催化剂，通过有机催化不对称氮杂-迈克尔加成将吡唑（16或20）与（E）-3-环戊基丙烯醛（23）进行对映选择性合成INCB018424 。迈克尔加合物 ( R )- 24和 ( R )- 27以良好的产率和高 ee 分离出来，并且很容易转化为 INCB018424。
• PROCESSES FOR PREPARING JAK INHIBITORS AND RELATED INTERMEDIATE COMPOUNDS
  申请人：Zhou Jiacheng

  公开号：US20100190981A1

  公开（公告）日：2010-07-29

  The present invention is related to processes for preparing chiral substituted pyrazolyl pyrrolo[2,3-d]pyrimidines of Formula III, and related synthetic intermediate compounds. The chiral substituted pyrazolyl pyrrolo[2,3-d]pyrimidines are useful as inhibitors of the Janus Kinase family of protein tyrosine kinases (JAKs) for treatment of inflammatory diseases, myeloproliferative disorders, and other diseases.

  本发明涉及制备手性取代吡唑基吡咯并[2,3-d]嘧啶的公式III的过程，以及相关的合成中间体化合物。这些手性取代吡唑基吡咯并[2,3-d]嘧啶可用作抑制Janus激酶家族蛋白酪氨酸激酶（JAKs）的药物，用于治疗炎症性疾病、骨髓增生性疾病和其他疾病。
• Regio- and Enantioselective Synthesis of N-Substituted Pyrazoles by Rhodium-Catalyzed Asymmetric Addition to Allenes
  作者：Alexander M. Haydl、Kun Xu、Bernhard Breit

  DOI：10.1002/anie.201501758

  日期：2015.6.8

  The rhodium‐catalyzed asymmetric N‐selective coupling of pyrazole derivatives with terminal allenes gives access to enantioenriched secondary and tertiary allylic pyrazoles, which can be employed for the synthesis of medicinally important targets. The reaction tolerates a large variety of functional groups and labelling experiments gave insights into the reaction mechanism. This new methodology was

  铑催化的吡唑衍生物与末端丙二烯的不对称 N 选择性偶联可以获得对映体富集的仲和叔烯丙基吡唑，可用于合成重要的药用靶标。该反应耐受多种官能团，标记实验使人们深入了解反应机制。这种新方法进一步应用于高效合成 JAK 1/2 抑制剂 ( R )-ruxolitinib。