1-(bromomethyl)-2,4-difluoro-5-methylbenzene | 315204-37-6

• 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-(bromomethyl)-2,4-difluoro-5-methylbenzene
• 英文别名: 1-bromomethyl-2,4-difluoro-5-methylbenzene；5-methyl-2,4-difluorobenzyl bromide
• CAS: 315204-37-6
• 化学式: C₈H₇BrF₂
• 分子量: 221.044
• InChiKey: ATFXKBKIXOZNMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(bromomethyl)-2,4-difluoro-5-methylbenzene 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 magnesium 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 生成 Boc-Aeg(C[z])-Aeg(F)-Aeg(G[z])-OBn
  参考文献：
  名称：

  短（F-）PNAs的改进的大规模液相合成和高温NMR表征

  摘要：

  我们报告了F-PNA三聚体10和PNA三聚体11的大规模合成。关键的改进是（2,4-二氟-5-甲基苯基）乙酸的简便两步合成（2）。相应的F-PNA低聚物10的水溶性是通过合成溶解度增强剂5a来实现的，该增强剂具有两个带正电且仅由PNA固有的结构元素组成。受保护且未配对的PNA n单体存在于2 n个构象异构体的混合物中，它们经历缓慢交换并导致复杂的NMR光谱。通过记录1 H-和13改进了结构分析高于聚结点的高温下的C-NMR谱图。完全受保护的主链衍生物在预期的地方显示出剧烈的共振，并且受保护的PNA的光谱显着简化，从而首次得以解释。修剪器10和11都被视为基于PNA的自我复制系统的构建块。

  DOI：

  10.1002/hlca.201100243
• 作为产物：
  描述：

  在 N-溴代丁二酰亚胺(NBS) 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-(bromomethyl)-2,4-difluoro-5-methylbenzene
  参考文献：
  名称：

  Syntheses of 1-[(2-Hydroxyethoxy)methyl]- and 1-[(1,3-Dihydroxy-2-Propoxy)methyl]- Derivatives of 5-Substituted-2,4-difluorobenzene: Unnatural Acyclo Thymidine Mimics for Evaluation as Anticancer and Antiviral Agents

  摘要：

  A group of 1 -[(2-hydroxyethoxy)methyl] - (12) and 1-[(1,3-dihydroxy-2-propoxy)methyl]- (13) derivatives of 2,4-difluorobenzene possessing a variety of C-5 substituents (R = Me, H, I, NO(2)) were designed with the expectation that they may serve as acyclic 5-substituted-2'-deoxyuridine (thymidine) mimics. Compounds 12 and 13 (R= Me, H, I) were inactive as anticancer agents (CC(50) = 10(-3) to 10(-4) M range), whereas the 5-nitro compounds (12d, 13d) exhibided weak-to-moderate cytotoxicity (ICC(50) = 10(-5) to 10(-6) M range) against a variety of cancer cell lines. All compounds prepared (12a-d, 13a-d) were inactive as antiviral agents in a broad-spectrum antiviral screen that also included the human immunodeficiency virus (HIV-1 and HIV-2) and herpes simplex virus(HSV-1 and HSV-2).

  DOI：

  10.1080/15257770008033850

文献信息

• Heterocyclic derivatives and use thereof
  申请人：C&C RESEARCH LABORATORIES

  公开号：US10023591B2

  公开（公告）日：2018-07-17

  A heterocyclic derivative represented by formula (I), or a pharmaceutically acceptable salt or a stereoisomer thereof, which has an inhibitory effect on the activation of STAT3 protein, and is useful for the prevention or treatment of diseases associated with the activation of STAT3 protein.

  一种由式（I）代表的杂环衍生物或其药学上可接受的盐或立体异构体，对 STAT3 蛋白的活化具有抑制作用，可用于预防或治疗与 STAT3 蛋白活化相关的疾病。
• WO2016/89060
  申请人：——

  公开号：——

  公开（公告）日：——
• HETEROCYCLIC DERIVATIVES AND USE THEREOF
  申请人：C&C Research Laboratories

  公开号：EP3227270A2

  公开（公告）日：2017-10-11
• Syntheses of 1-[(2-Hydroxyethoxy)methyl]- and 1-[(1,3-Dihydroxy-2-Propoxy)methyl]- Derivatives of 5-Substituted-2,4-difluorobenzene: Unnatural Acyclo Thymidine Mimics for Evaluation as Anticancer and Antiviral Agents
  作者：Zhi-Xian Wang、Weili Duan、Leonard I. Wiebe、Erik De Clercq、Jan Balzarini、Edward E. Knaus

  DOI：10.1080/15257770008033850

  日期：2000.9

  A group of 1 -[(2-hydroxyethoxy)methyl] - (12) and 1-[(1,3-dihydroxy-2-propoxy)methyl]- (13) derivatives of 2,4-difluorobenzene possessing a variety of C-5 substituents (R = Me, H, I, NO(2)) were designed with the expectation that they may serve as acyclic 5-substituted-2'-deoxyuridine (thymidine) mimics. Compounds 12 and 13 (R= Me, H, I) were inactive as anticancer agents (CC(50) = 10(-3) to 10(-4) M range), whereas the 5-nitro compounds (12d, 13d) exhibided weak-to-moderate cytotoxicity (ICC(50) = 10(-5) to 10(-6) M range) against a variety of cancer cell lines. All compounds prepared (12a-d, 13a-d) were inactive as antiviral agents in a broad-spectrum antiviral screen that also included the human immunodeficiency virus (HIV-1 and HIV-2) and herpes simplex virus(HSV-1 and HSV-2).
• Improved Large-Scale Liquid-Phase Synthesis and High-Temperature NMR Characterization of Short ­(F-)PNAs
  作者：Tobias A. Plöger、Günter von Kiedrowski

  DOI：10.1002/hlca.201100243

  日期：2011.11

  unpaired PNA n‐mers exist in a mixture of 2n conformers undergoing slow exchange and leading to complicated NMR spectra. Structure analysis was improved by recording 1H‐ and 13C‐NMR spectra at elevated temperatures above the coalescence point. Fully protected backbone derivatives show sharp resonances where expected, and spectra of protected PNAs are remarkably simplified, thereby allowing an interpretation

  我们报告了F-PNA三聚体10和PNA三聚体11的大规模合成。关键的改进是（2,4-二氟-5-甲基苯基）乙酸的简便两步合成（2）。相应的F-PNA低聚物10的水溶性是通过合成溶解度增强剂5a来实现的，该增强剂具有两个带正电且仅由PNA固有的结构元素组成。受保护且未配对的PNA n单体存在于2 n个构象异构体的混合物中，它们经历缓慢交换并导致复杂的NMR光谱。通过记录1 H-和13改进了结构分析高于聚结点的高温下的C-NMR谱图。完全受保护的主链衍生物在预期的地方显示出剧烈的共振，并且受保护的PNA的光谱显着简化，从而首次得以解释。修剪器10和11都被视为基于PNA的自我复制系统的构建块。