2-Bromo-3,6-bis(methoxymethoxy)naphthalene | 1368254-70-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Bromo-3,6-bis(methoxymethoxy)naphthalene
• CAS: 1368254-70-9
• 化学式: C₁₄H₁₅BrO₄
• 分子量: 327.175
• InChiKey: RBUFOUIUEGUVGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Bromo-3,6-bis(methoxymethoxy)naphthalene 在 盐酸 、 manganese(IV) oxide 、 正丁基锂 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 46.0h， 生成
  参考文献：
  名称：

  Alternative simple and effective synthesis of (di)benzoxanthones and their functions toward fluorescent dyes

  摘要：

  (对)苯基 greens 通过脱水反应制备，其中使用适量的 K₂CO₃ 催化剂可以显著提高产率。二苯基 greens 的多变羰基组分可以通过化学转化得到发光材料。 (注：C. 版权所有，内容仅供参考）

  DOI：

  10.1016/j.tet.2012.12.035
• 作为产物：
  描述：

  3-bromonaphthalene-2,7-diol 、 氯甲基甲基醚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.5h， 以86%的产率得到2-Bromo-3,6-bis(methoxymethoxy)naphthalene
  参考文献：
  名称：

  Exhaustive Syntheses of Naphthofluoresceins and Their Functions

  摘要：

  Naphthofluorescein and/or seminaphthofluorescein derivatives possessing the additional benzene units to one or both sides of fluorescein were exhaustively constructed through Friedel-Crafts type reactions between corresponding aroylbenzoic acids and dihydroxynaphthalenes. Compound 4 works as a one-dye pH indicator, which shows red in strong acid condition and blue in basic solution. Compound 23 (diacetate of compound 4) shows good transitivity to the HEK 293 cells and acts as a fluorescent pigment for the living cell imaging. Compounds 5, 6, and 9 show fluorescent emission in the NIR region (>700 nm) and imply the potentialities of NIR fluorescent probes.

  DOI：

  10.1021/jo300177b

文献信息

• Formation of Phenalenone Skeleton by an Unusual Rearrangement Reaction
  作者：Sayaka Sasaki、Eriko Azuma、Takahiro Sasamori、Norihiro Tokitoh、Kouji Kuramochi、Kazunori Tsubaki

  DOI：10.1021/acs.orglett.7b02305

  日期：2017.9.15

  The frame rearrangement reaction of dinaphthyl ketones, possessing hydroxy groups at appropriate positions, into phenalenone derivatives under acidic conditions was discovered serendipitously. Although this rearrangement had limited scope, its mechanism was unusual, involving the division of naphthalene rings into one phenalenone ring and one benzene ring. The reaction mechanism was elucidated by direct

  偶然发现了在酸性条件下在适当位置具有羟基的二萘甲酮向苯丙烯酮衍生物的骨架重排反应。尽管这种重排的范围有限，但是其机理却很不寻常，涉及将萘环分为一个菲拉烯酮环和一个苯环。通过使用1 H NMR测量直接确定中间结构来阐明反应机理。预计生成的非对苯二酚是天然产物和功能材料的关键中间体。
• Syntheses and properties of the V-shaped dimeric xanthene dyes
  作者：Akari Yamagami、Hina Ishimura、Akane Katori、Kouji Kuramochi、Kazunori Tsubaki

  DOI：10.1039/c6ob01967f

  日期：——

  Two new types of V-shaped dimeric xanthene fluorescent dyes were synthesized and evaluated in terms of their optical properties. Based on differences in their resonance forms, these V-shaped dyes were able to adopt four different protonation states (i.e., cationic, neutral, monoanionic and dianionic states) depending on their external environment. Notably, these compounds allowed for the bright fluorescent

  合成了两种新型的V型二聚meric吨荧光染料，并对其光学性质进行了评估。基于它们的共振形式的差异，这些V形染料能够根据其外部环境采用四种不同的质子化状态（即阳离子，中性，单阴离子和二阴离子状态）。值得注意的是，当这些化合物作为相应的二乙酰化物质应用于细胞时，它们可以使NIH3T3细胞产生明亮的荧光成像。
• Exhaustive Syntheses of Naphthofluoresceins and Their Functions
  作者：Eriko Azuma、Naoko Nakamura、Kouji Kuramochi、Takahiro Sasamori、Norihiro Tokitoh、Ikuko Sagami、Kazunori Tsubaki

  DOI：10.1021/jo300177b

  日期：2012.4.6

  Naphthofluorescein and/or seminaphthofluorescein derivatives possessing the additional benzene units to one or both sides of fluorescein were exhaustively constructed through Friedel-Crafts type reactions between corresponding aroylbenzoic acids and dihydroxynaphthalenes. Compound 4 works as a one-dye pH indicator, which shows red in strong acid condition and blue in basic solution. Compound 23 (diacetate of compound 4) shows good transitivity to the HEK 293 cells and acts as a fluorescent pigment for the living cell imaging. Compounds 5, 6, and 9 show fluorescent emission in the NIR region (>700 nm) and imply the potentialities of NIR fluorescent probes.
• Alternative simple and effective synthesis of (di)benzoxanthones and their functions toward fluorescent dyes
  作者：Eriko Azuma、Kouji Kuramochi、Kazunori Tsubaki

  DOI：10.1016/j.tet.2012.12.035

  日期：2013.2

  (Di)benzoxanthones possessing additional benzene units on one or both sides of xanthone were prepared via dehydration of the corresponding dihydroxybenzophenone, where a catalytic amount of K2CO3 dramatically increased the yields. Chemical transformations of the versatile carbonyl groups of (di) benzoxanthones could derive fluorescent materials. (C) 2012 Elsevier Ltd. All rights reserved.

  (对)苯基 greens 通过脱水反应制备，其中使用适量的 K₂CO₃ 催化剂可以显著提高产率。二苯基 greens 的多变羰基组分可以通过化学转化得到发光材料。 (注：C. 版权所有，内容仅供参考）