1,2-bis(dibromomethyl)-3-methoxybenzene | 69813-89-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2-bis(dibromomethyl)-3-methoxybenzene
• CAS: 69813-89-4
• 化学式: C₉H₈Br₄O
• 分子量: 451.778
• InChiKey: QMRWUXINMKQRDW-UHFFFAOYSA-N

物化性质

• 沸点：
  393.0±42.0 °C(Predicted)
• 密度：
  2?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-bis(dibromomethyl)-3-methoxybenzene 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以53%的产率得到1,2-二溴甲基-3-甲氧基苯
  参考文献：
  名称：

  （+/-）-利西里利德B的总合成。

  摘要：

  DOI：

  10.1021/ja003272a
• 作为产物：
  描述：

  2-(bromomethyl)-3-(dibromomethyl)anisole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 12.0h， 以98%的产率得到1,2-bis(dibromomethyl)-3-methoxybenzene
  参考文献：
  名称：

  Box, Vernon, G. S.; Yiannikouros, George P., Heterocycles, 1990, vol. 31, # 7, p. 1261 - 1270

  摘要：

  DOI：

文献信息

• Photothermal Side-Chain Bromination of Methyl-, Dimethyl-, and Trimethylbenzenes with<i>N</i>-Bromosuccinimide
  作者：Shuntaro Mataka、Guo-Bin Liu、Tsuyoshi Sawada、Masayoshi Kurisu、Masashi Tashiro

  DOI：10.1246/bcsj.67.1113

  日期：1994.4

  Tri- and dibromination of methyl-, dimethyl-, and trimethylbenzenes with N-bromosuccinimide were accomplished by photothermal reaction with a tungsten lamp in carbon tetrachloride or benzene. (Dibromomethyl)arenes and (tribromomethyl) derivatives were produced depending upon a solvent used and a substituent on the benzene ring. In the bromination of methylbenzenes without a substituent on the ortho-position, (tribromomethyl)benzenes were formed. On the other hand, ortho-substituted methylbenzenes gave (dibromomethyl)benzenes. α,β-Dibromo-1,2-diarylstilbenes were formed via the debrominative carbon–carbon coupling reaction of (tribromomethyl) benzenes upon irradiation with a tungsten lamp.

  采用钨丝灯在四氯化碳或苯溶剂中进行光热反应，实现了N-溴代琥珀酰亚胺对甲基苯、二甲基苯和三甲基苯的二溴化和三溴化。根据所用溶剂和苯环上取代基的不同，生成了二溴甲基芳烃和三溴甲基衍生物。在邻位无取代基的甲基苯的溴化反应中，生成了三溴甲基苯。另一方面，邻位取代的甲基苯生成了二溴甲基苯。通过三溴甲基苯在钨丝灯照射下的脱溴碳-碳偶联反应，生成了α,β-二溴-1,2-二芳基苯乙烯。
• On the Total Synthesis and Determination of the Absolute Configuration of Rishirilide B: Exploitation of Subtle Effects to Control the Sense of Cycloaddition of o-Quinodimethides
  作者：Kana Yamamoto、Martin F. Hentemann、John G. Allen、Samuel J. Danishefsky

  DOI：10.1002/chem.200304931

  日期：2003.7.21

  The total synthesis of racemic rishirilide B has been accomplished. The synthesis serves to define the relative relationships of its stereogenic centers. Also, starting with readily available chiral pool, ent-rishirilide B was synthesized, thereby demonstrating that natural configuration of rishirilide B. The defining step in our total synthesis is the facile cycloreversion of the bis(siloxy)benzocyclobutane

  外消旋利什利利德B的全合成已完成。该合成用于定义其立体遗传中心的相对关系。同样，从容易获得的手性库开始，合成了利什利利德B的对映体，从而证明了利什利利德B的天然构型。我们总合成中的决定性步骤是双（甲硅烷氧基）苯并环丁烷和分子间的邻二喹二甲醚Diels的容易的环还原。 -Al木环加成。我们认为，这一步骤中严格的区域化学指导是由于邻喹啉二烯二烯的对称干扰芳香族OTBS基团的供电子作用与亲二烯体（烯二酮）的反应性差（受羟基调节）的啮合而产生的。在alpha位置。在二烯二烯亲二烯体的背景下，其邻位酮功能的羟基定向活化假说的有效性值得进一步研究。这种类型的活化可以在区分有机底物中关键的密切相关的官能团的反应性谱中找到更广泛的应用。
• 2,3-萘二甲酰亚胺类衍生物及其制备方法和 应用
  申请人：山东大学

  公开号：CN108929260B

  公开（公告）日：2020-05-26

  本发明提供一种化合物或其可药用盐及其制备方法和应用，所述化合物对过表达AcrB的格兰阴性菌具有较好的抗菌增效活性及外排抑制活性。
• Design, synthesis and evaluation of a series of 5-methoxy-2,3-naphthalimide derivatives as AcrB inhibitors for the reversal of bacterial resistance
  作者：Chaobin Jin、Rawaf Alenazy、Yinhu Wang、Rumana Mowla、Yinhui Qin、Jin Quan Eugene Tan、Natansh Deepak Modi、Xinjie Gu、Steven W. Polyak、Henrietta Venter、Shutao Ma

  DOI：10.1016/j.bmcl.2019.02.003

  日期：2019.4

  A series of novel 5-methoxy-2,3-naphthalimide derivatives were designed, synthesized and evaluated for their biological activities. In particular, the ability of the compounds to synergize with antimicrobials, to inhibit Nile Red efflux, and to target AcrB was assayed. The results showed that the most of the tested compounds more sensitized the Escherichia coli BW25113 to the antibiotics than the parent compounds 7 c and 15, which were able to inhibit Nile Red efflux. Significantly, compound A5 possessed the most potent antibacterial synergizing ac-tivity in combination with levofloxacin by 4 times and 16 times at the concentration of 8 and 16 mu g/mL, re-spectively, whilst A5 could effectively abolish Nile Red efflux at 100 mu M. Additionally, target effect of A5 was confirmed in the outer- or inner membrane permeabilization assays. Therefore, A5 is an excellent lead com-pound for further structural optimization.
• Mataka Shuntaro, Liu Guo-Bin, Sawada Tsuyoshi, Kurisu Masayoshi, Tashiro +, Bull. Chem. Soc. Jap, 67 (1994) N 4, S 1113-1119
  作者：Mataka Shuntaro, Liu Guo-Bin, Sawada Tsuyoshi, Kurisu Masayoshi, Tashiro +

  DOI：——

  日期：——