(E)-1-(3-bromoprop-1-en-1-yl)-2-chlorobenzene | 881404-67-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-(3-bromoprop-1-en-1-yl)-2-chlorobenzene
• 英文别名: 1-[(E)-3-bromoprop-1-enyl]-2-chlorobenzene
• CAS: 881404-67-7
• 化学式: C₉H₈BrCl
• 分子量: 231.52
• InChiKey: JJJYDUKZFZGPHS-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-bromoprop-1-en-1-yl)-2-chlorobenzene 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  钌（II）-Amm-Pheox催化的重氮Weinreb酰胺分子间和分子内环丙烷化

  摘要：

  使用手性钌（II）-Amm- Pheox催化剂已经实现了一系列重氮Weinreb酰胺和反式烯丙基重氮Weinreb酰胺衍生物的分子间和分子内环丙烷化，从而以优异的收率（高达99％）获得了相应的手性环丙基Weinreb酰胺）具有出色的对映选择性（高达99％ee）。手性产物可以容易地进行有用的合成转化，以高产率和对映选择性得到相应的醛，醇和酮。

  DOI：

  10.1002/adsc.201601345
• 作为产物：
  描述：

  邻氯肉桂醛 在 sodium tetrahydroborate 、 三溴化磷 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.5h， 生成 (E)-1-(3-bromoprop-1-en-1-yl)-2-chlorobenzene
  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

文献信息

• P-Chiral Monophosphorus Ligands for Asymmetric Copper-Catalyzed Allylic Alkylation
  作者：Wenrui Xiong、Guangqing Xu、Xinhong Yu、Wenjun Tang

  DOI：10.1021/acs.organomet.9b00194

  日期：2019.10.28

  Asymmetric copper-catalyzed allylic alkylation between allyl bromides and alkyl Grignard reagents using a P-chiral monophosphorus ligand is described. A range of terminal olefins bearing tertiary or quaternary carbon centers were formed in good branched/linear selectivities and excellent enantioselectivities at copper loadings as low as 0.5 mol %.

  描述了使用P-手性单磷配体在烯丙基溴和烷基格氏试剂之间的不对称铜催化的烯丙基烷基化。在低至0.5mol％的铜负载下，形成具有良好支化/线性选择性和优异对映选择性的一系列带有叔碳或季碳中心的末端烯烃。
• 4-Alkyl- and 4-Cinnamylglutamic Acid Analogues Are Potent GluR5 Kainate Receptor Agonists
  作者：Concepción Pedregal、Iván Collado、Ana Escribano、Jesús Ezquerra、Carmen Domínguez、Ana I. Mateo、Almudena Rubio、S. Richard Baker、John Goldsworthy、Rajender K. Kamboj、Barbara A. Ballyk、Ken Hoo、David Bleakman

  DOI：10.1021/jm9911682

  日期：2000.5.1

  Enantiomerically pure (2S,4R)-4-substituted glutamic acids were prepared and tested for homomeric GluR5 and GluR6 kainate subtype receptor affinity. Some of the 4-cinnamyl analogues showed high selectivity and potency (K(i) < 25 nM) for the GluR5 receptors. The greatest selectivity and potency were achieved with the 3-(2-naphthyl)prop-2-enyl compound. This compound, LY339434, has negligible activity

  制备对映体纯的（2S，4R）-4-取代的谷氨酸，并测试其同质的GluR5和GluR6海藻酸酯亚型受体亲和力。一些4-肉桂基类似物对GluR5受体显示出高选择性和强效性（K（i）<25 nM）。用3-（2-萘基）丙-2-烯基化合物获得最大的选择性和效力。该化合物LY339434对AMPA和红藻氨酸受体GluR1，-2，-4和-6的活性可忽略不计。虽然，LY339434在文化海马神经元（大约EC（50）为2.5 microM）对NMDA受体显示激动剂活性，我们认为LY339434应该是研究GluR5海藻酸酯受体功能作用的有用药理工具。
• Chiral Brønsted Acid Catalyzed Enantioselective Phosphonylation of Allylamine via Oxidative Dehydrogenation Coupling
  作者：Ming-Xing Cheng、Ran-Song Ma、Qiang Yang、Shang-Dong Yang

  DOI：10.1021/acs.orglett.6b01514

  日期：2016.7.1

  A new strategy for the synthesis of chiral α-amino phosphonates by enantioselective C–H phosphonylation of allylamine with phosphite in the presence of a chiral Brønsted acid catalyst has been developed. This protocol successfully integrates direct C–H oxidation with asymmetric phosphonylation and exhibits high enantioselectivity.

  在手性布朗斯台德酸催化剂的存在下，开发了一种通过烯丙基胺与亚磷酸酯的对映体C–H膦酰基对映体选择性合成手性α-氨基膦酸酯的新策略。该方案成功地将直接的C–H氧化与不对称的膦酰化反应相结合，并显示出高对映选择性。
• Reusable and highly enantioselective water-soluble Ru(II)-<i>Amm</i>-Pheox catalyst for intramolecular cyclopropanation of diazo compounds
  作者：Hamada S A Mandour、Yoko Nakagawa、Masaya Tone、Hayato Inoue、Nansalmaa Otog、Ikuhide Fujisawa、Soda Chanthamath、Seiji Iwasa

  DOI：10.3762/bjoc.15.31

  日期：——

  highly enantioselective catalyst for the intramolecular cyclopropanation of various diazo ester and Weinreb amide derivatives was developed. The reactions catalyzed by a water-soluble Ru(II)-Amm-Pheox catalyst proceeded smoothly at room temperature, affording the corresponding bicyclic cyclopropane ring-fused lactones and lactams in high yields (up to 99%) with excellent enantioselectivities (up to

  开发了一种可重用和高对映选择性的催化剂，用于各种重氮酯和Weinreb酰胺衍生物的分子内环丙烷化反应。水溶性Ru（II）-Amm- Pheox催化剂催化的反应在室温下顺利进行，从而以高收率（高达99％）提供了相应的双环环丙​​烷环稠合内酯和内酰胺，并具有出色的对映选择性（高达99） ％ee）。在筛选各种催化剂后，具有铵基的Ru（II）-Amm - Pheox配合物被证明对于在水/醚双相介质中的分子内环丙烷化反应至关重要。水溶性催化剂可以重复使用至少六次，而收率和对映选择性几乎没有损失。
• A Thermal Dehydrogenative Diels–Alder Reaction of Styrenes for the Concise Synthesis of Functionalized Naphthalenes
  作者：Laura S. Kocsis、Erica Benedetti、Kay M. Brummond

  DOI：10.1021/ol301938z

  日期：2012.9.7

  Functionalized naphthalenes are valuable building blocks in many important areas. A microwave-assisted, intramolecular dehydrogenative Diels–Alder reaction of styrenyl derivatives to provide cyclopenta[b]naphthalene substructures not previously accessible using existing synthetic methods is described. The synthetic utility of these uniquely functionalized naphthalenes was demonstrated by a single-step

  功能化萘是许多重要领域的宝贵组成部分。描述了苯乙烯基衍生物的微波辅助分子内脱氢 Diels-Alder 反应，以提供以前使用现有合成方法无法获得的环戊二烯 [ b ] 萘亚结构。通过将这些环加合物之一一步转化为与 Prodan 结构相似的荧光团，证明了这些独特功能化萘的合成效用。