2-Bromo-1,6-bis(methoxymethoxy)naphthalene | 1368254-73-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Bromo-1,6-bis(methoxymethoxy)naphthalene
• CAS: 1368254-73-2
• 化学式: C₁₄H₁₅BrO₄
• 分子量: 327.175
• InChiKey: RQZACFFBWWLTGK-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-1,6-bis(methoxymethoxy)naphthalene 在 盐酸 、 正丁基锂 、 甲烷磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 甲苯 为溶剂， 反应 8.0h， 生成 7',17'-Dihydroxyspiro[2-benzofuran-3,13'-2-oxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-1(14),3(12),4(9),5,7,10,15(20),16,18,21-decaene]-1-one
  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
• 作为产物：
  描述：

  2-bromo-6-methoxynaphthalen-1-ol 在 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 21.5h， 生成 2-Bromo-1,6-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

• 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）
• 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.