2-formyl-1,8-bis(methoxymethoxy)naphthalene | 865873-39-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-formyl-1,8-bis(methoxymethoxy)naphthalene
• 英文别名: 1,8-bis(methoxymethoxy)-2-naphthaldehyde；1,8-bis(methoxymethoxy)naphthalene-2-carbaldehyde
• CAS: 865873-39-8
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: SOHPYIMCMVIXII-UHFFFAOYSA-N

物化性质

• 沸点：
  448.7±45.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-formyl-1,8-bis(methoxymethoxy)naphthalene 在 盐酸 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 6.0h， 以98%的产率得到1,8-二羟基-2-萘甲醛
  参考文献：
  名称：

  基于1,8-萘二醇的不对称双核配体。

  摘要：

  据报道，容易合成2-甲酰基-1，8-萘二醇。通过合成双核配体L（4-）（H（4）L = N，N'-bis（ 2-（1,8-萘二醇）亚甲基）丙二胺）。H（4）L与乙酸铜的反应导致形成不对称双核Cu（II）配合物[LCu（2）]（3），该配合物已通过单晶X射线衍射进行了结构表征。一个Cu（II）离子通过L（4-）的N（2）O（2）隔室配位，而另一个Cu（II）离子则通过L（4-）的O（4）隔室配位。由L（4-）的两个芳氧基官能团桥接。两个3的分子向二核实体3（2）的二聚化通过形成较弱的顶端Cu-O相互作用而发生。对温度依赖性磁化率测量值（2--290 K）的分析建立了牢固的二聚体交换耦合J（12）=-371 cm（-1）。这种强的超交换相互作用非常适合磁结构相关性，该磁结构相关性已针对双核双（酚盐）桥连的Cu（II）络合物建立，证明了苯酚和1,8-萘基芳基氧化物的电子等效性。

  DOI：

  10.1039/b507579c
• 作为产物：
  描述：

  1,8-二羟基萘 在 正丁基锂 、 四甲基乙二胺 、 sodium hydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 2-formyl-1,8-bis(methoxymethoxy)naphthalene
  参考文献：
  名称：

  Optically Triggered Stepwise Double-Proton Transfer in an Intramolecular Proton Relay: A Case Study of 1,8-Dihydroxy-2-naphthaldehyde

  摘要：

  1,8-Dihydroxy-2-naphthaldehyde (DHNA), having doubly intramolecular hydrogen bonds, was strategically designed and synthesized in an aim to probe a long-standing fundamental issue regarding synchronous versus asynchronous double-proton transfer in the excited state. In cyclohexane, DHNA shows the lowest lying S-0 -> S-1 (pi pi*) absorption at similar to 400 nm. Upon excitation, two large Stokes shifted emission bands maximized at 520 and 650 nm are resolved, which are ascribed to the tautomer emission resulting from the first and second proton-transfer products, denoted by TA* and TB*, respectively. The first proton transfer (DHNA* -> TA*) is ultrafast (< system response of 150 fs), whereas the second proton transfer is reversible, for which the rates of forward (TA* -> TB*) and backward (TA* -> TB*) proton transfer were determined to be (1.7 ps)(-1) and (3.6 ps)(-1), respectively. The fast equilibrium leads to identical population lifetimes of similar to 54 ps for both TA* and TB* tautomers. Similar excited-state double-proton transfer takes place for DHNA in a single crystal, resulting in TA* (560 nm) and TB* (650 nm) dual-tautomer emission. A comprehensive 2D plot of reaction potential energy surface further proves that the sequential two-step proton motion is along the minimum energetic pathway firmly supporting the experimental results. Using DHNA as a paradigm, we thus demonstrate unambiguously a stepwise, proton-relay type of intramolecular double-proton transfer reaction in the excited state, which should gain fundamental understanding of the multiple proton transfer reactions.

  DOI：

  10.1021/jacs.5b08562

文献信息

• Highly Selective Visual Detection of Cu(II) Utilizing Intramolecular Hydrogen Bond-Stabilized Merocyanine in Aqueous Buffer Solution
  作者：Zhao-Qi Guo、Wei-Qiang Chen、Xuan-Ming Duan

  DOI：10.1021/ol100381g

  日期：2010.5.21

  A Cu2+-specific colorimetric sensor 1, which is stabilized by an intramolecular hydrogen bonding, was designed and developed. The color of 1 changes from purple to blue on addition of 1.0 mu M Cu2+ in aqueous buffer solution, which can be detected by the naked eye. The analytical detection limit for Cu2+ by the naked eye is as low as 1.0 mu M. The stoichiometry for 1 and Cu2+ in complex is 2:1 in aqueous solution.