(E)-1-(3-bromoprop-1-en-1-yl)-2,4-dichlorobenzene | 1346682-13-0

• 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)-2,4-dichlorobenzene
• 英文别名: (E)-1-(3-bromoprop-1-enyl)-2,4-dichlorobenzene；2,4-dichlorocinnamyl bromide；1-[(E)-3-bromoprop-1-enyl]-2,4-dichlorobenzene
• CAS: 1346682-13-0
• 化学式: C₉H₇BrCl₂
• 分子量: 265.965
• InChiKey: VGFWKONURKQUGQ-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  12
• 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)-2,4-dichlorobenzene 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 0.5h， 生成 2-((but-3-yn-2-yloxy)methyl)-3-(2,4-dichlorophenyl)oxirane
  参考文献：
  名称：

  金催化的分子内亲电加成和苯并环合反应合成芳基萘木质素支架

  摘要：

  提出了一种以高产率产生包含芳基萘木脂体骨架的化合物的分子内方法。它涉及羰基对芳基炔的连续分子内亲电攻击，然后由金盐催化苯环化。AuCl 3与AgSbF 6结合使用效果更好。某些产品已被转化为芳基萘内酯天然产品，例如司法正义素E，黄花青素C和逆转录调节素B。

  DOI：

  10.1021/jo201918d
• 作为产物：
  描述：

  (E)-3-(2,4-dichlorophenyl)acrylaldehyde 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)-2,4-dichlorobenzene
  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

• 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。
• Highly Diastereoselective Synthesis of Dihydro‐benzoimidazo‐[1,3]‐thiazines via Electro‐oxidative Selenocyclization of Thioallyl Benzoimidazoles
  作者：Atreyee Halder、Kingshuk Mahanty、Debabrata Maiti、Suman De Sarkar

  DOI：10.1002/asia.202101033

  日期：2021.12

  A series of dihydro-benzoimidazo-thiazine derivatives displaying exclusive diastereoselectivity has been synthesized proficiently via external chemical oxidant and metal-free selenocyclization methodology. This mild electro-oxidative protocol operates in an undivided electrochemical cell at ambient temperature under air, exhibiting decent functional group tolerance and excellent yields.

  通过外部化学氧化剂和无金属硒环化方法，已经合成了一系列具有独特非对映选择性的二氢苯并咪唑并噻嗪衍生物。这种温和的电氧化方案在空气中的环境温度下在未分开的电化学电池中运行，表现出良好的官能团耐受性和出色的产率。
• Stereoselective Halocyclization of Alkenes With <i>N</i> -Acyl Hemiaminal Nucleophiles
  作者：Na Liu、Hao-Yuan Wang、Wei Zhang、Zhi-Hong Jia、Ilia A. Guzei、Hua-dong Xu、Weiping Tang

  DOI：10.1002/chir.22219

  日期：2013.11

  Halocyclization of alkenes was realized using N‐acylhemiaminal nucleophiles. High diastereoselectivity could be achieved for the formation of three stereogenic centers in this halogen‐mediated cyclization reaction. We also demonstrated that enantioselective bromocyclization of alkenes using N‐acylhemiaminal nucleophiles was possible. Chirality 25:805–809, 2013. © 2013 Wiley Periodicals, Inc.

  烯烃的卤代化是通过使用N酰基半乳糖亲核试剂实现的。在此卤素介导的环化反应中，形成三个立体异构中心可实现较高的非对映选择性。我们还证明了使用N酰基半乳糖亲核试剂对烯烃进行对映选择性溴环化是可能的。手性25：805–809，2013年。©2013 Wiley Periodicals，Inc.
• Inter- and Intramolecular Cyclopropanations of Diazo Weinreb Amides Catalyzed by Ruthenium(II)-<i>Amm</i> -Pheox
  作者：Hamada S. A. Mandour、Soda Chanthamath、Kazutaka Shibatomi、Seiji Iwasa

  DOI：10.1002/adsc.201601345

  日期：2017.5.17

  diazo Weinreb amides and trans-allylic diazo Weinreb amide derivatives have been achieved using chiral ruthenium(II)-Amm-Pheox catalyst to give the corresponding chiral cyclopropyl Weinreb amides in excellent yield (up to 99%) with excellent enantioselectivity (up to 99% ee). The chiral products could easily undergo useful synthetic transformations to give the corresponding aldehydes, alcohols and

  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。
• Novel Inhibitors of Staphyloxanthin Virulence Factor in Comparison with Linezolid and Vancomycin versus Methicillin-Resistant, Linezolid-Resistant, and Vancomycin-Intermediate <i>Staphylococcus aureus</i> Infections in Vivo
  作者：Shuaishuai Ni、Hanwen Wei、Baoli Li、Feifei Chen、Yifu Liu、Wenhua Chen、Yixiang Xu、Xiaoxia Qiu、Xiaokang Li、Yanli Lu、Wenwen Liu、Linhao Hu、Dazheng Lin、Manjiong Wang、Xinyu Zheng、Fei Mao、Jin Zhu、Lefu Lan、Jian Li

  DOI：10.1021/acs.jmedchem.7b00949

  日期：2017.10.12

  Our previous work (Wang et al. J. Med. Chem. 2016, 59, 4831-4848) revealed that effective benzocycloalkane-derived staphyloxanthin inhibitors against methicillin-resistant Staphylococcus aureus (S. aureus) infections were accompanied by poor water solubility and high hERG inhibition and dosages (preadministration). In this study, 92 chroman and coumaran derivatives as novel inhibitors have been addressed for overcoming deficiencies above. Derivatives 69 and 105 displayed excellent pigment inhibitory activities and low hERG inhibition, along with improvement of solubility by salt type selection. The broad and significantly potent antibacterial spectra of 69 and 105 were displayed first with normal administration in the livers and hearts in mice against pigmented S. aureus Newman, Mu50 (vancomycin-intermediate S. aureus), and NRS271 (linezolid-resistant S. aureus), compared with linezolid and vancomycin. In summary, both 69 and 105 have the potential to be developed as good antibacterial candidates targeting virulence factors.