1-bromo-4-(5-bromo-1-pentynyl)benzene | 1333171-45-1

• 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: 1-bromo-4-(5-bromo-1-pentynyl)benzene
• 英文别名: 1-Bromo-4-(5-bromopent-1-ynyl)benzene
• CAS: 1333171-45-1
• 化学式: C₁₁H₁₀Br₂
• 分子量: 302.008
• InChiKey: LRFRPMZYVNCUJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  1-bromo-4-(5-bromo-1-pentynyl)benzene 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium hydride 、 potassium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 生成 (6S)-6-({5-[4'-(difluoromethoxy)[1,1'-biphenyl]-4-yl]-4-pentynyl}oxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of Varied Ether Linker Analogues of the Antitubercular Drug (6S)-2-Nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824)

  摘要：

  New analogues of antitubercular drug PA-824 were synthesized, featuring alternative side chain ether linkers of varying size and flexibility, seeking drug candidates with enhanced metabolic stability and high efficacy. Both alpha-methyl substitution and removal of the benzylic methylene were broadly tolerated in vitro, with a biaryl example of the latter class exhibiting an 8-fold better efficacy than the parent drug in a mouse model of acute Mycobacterium tuberculosis infection and negligible fragmentation to an alcohol metabolite in liver microsomes. Extended linkers (notably propenyloxy, propynyloxy, and pentynyloxy) provided greater potencies against replicating M. tb (monoaryl analogues), with propynyl ethers being most effective under anaerobic (nonreplicating) conditions (mono/biaryl analogues). For benzyloxybenzyl and biaryl derivatives, aerobic activity was maximal with the original (OCH2) linker. One propynyloxy-linked compound displayed an 89-fold higher efficacy than the parent drug in the acute model, and it was slightly superior to antitubercular drug OPC-67683 in a chronic infection model.

  DOI：

  10.1021/jm200377r
• 作为产物：
  描述：

  5-(4-bromophenyl)pent-4-yn-1-ol 在 溴 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以49%的产率得到1-bromo-4-(5-bromo-1-pentynyl)benzene
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of Varied Ether Linker Analogues of the Antitubercular Drug (6S)-2-Nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824)

  摘要：

  New analogues of antitubercular drug PA-824 were synthesized, featuring alternative side chain ether linkers of varying size and flexibility, seeking drug candidates with enhanced metabolic stability and high efficacy. Both alpha-methyl substitution and removal of the benzylic methylene were broadly tolerated in vitro, with a biaryl example of the latter class exhibiting an 8-fold better efficacy than the parent drug in a mouse model of acute Mycobacterium tuberculosis infection and negligible fragmentation to an alcohol metabolite in liver microsomes. Extended linkers (notably propenyloxy, propynyloxy, and pentynyloxy) provided greater potencies against replicating M. tb (monoaryl analogues), with propynyl ethers being most effective under anaerobic (nonreplicating) conditions (mono/biaryl analogues). For benzyloxybenzyl and biaryl derivatives, aerobic activity was maximal with the original (OCH2) linker. One propynyloxy-linked compound displayed an 89-fold higher efficacy than the parent drug in the acute model, and it was slightly superior to antitubercular drug OPC-67683 in a chronic infection model.

  DOI：

  10.1021/jm200377r

文献信息

• Accessing Polycyclic Heteroarenes Enabled by Copper-Catalyzed Aerobic Oxidative C–H/C–H [4 + 2] Annulation of 3-Arylindole Derivatives
  作者：Yuanyuan Yue、Yan Yang、Chunying Sun、Junli Chao、Yaqing Ye、Xiaohui Guo、Jianming Liu

  DOI：10.1021/acs.orglett.1c03686

  日期：2022.1.21

  polycyclic aromatic hydrocarbons are delivered at room temperature by copper-catalyzed aerobic oxidative C–H/C–H [4 + 2] annulation of alkyl-substituted 3-arylindole derivatives. Specifically, dual aryl C–H functionalization is furnished under mild conditions through the 1,2-migration of copper catalyst and regioselective alkyne insertion. Mechanistic experiments demonstrate that the C–H bond cleavage

  几种多环芳烃在室温下通过铜催化的好氧氧化 C–H/C–H [4 + 2] 环化烷基取代的 3-芳基吲哚衍生物来传递。具体而言，通过铜催化剂的 1,2-迁移和区域选择性炔烃插入，在温和条件下提供双芳基 C-H 官能化。机械实验表明，吲哚和苯环上的 C-H 键断裂不参与限速步骤。