1,8-diacetoxynaphthalene | 6566-25-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,8-diacetoxynaphthalene
• 英文别名: 1,8-Diacetoxy-naphthalin；(8-Acetyloxynaphthalen-1-yl) acetate
• CAS: 6566-25-2
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: ODPOHJGQBBQWND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  1,8-diacetoxynaphthalene 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 0.75h， 以90%的产率得到5-acetoxy-3-bromo-1,4-naphthoquinone
  参考文献：
  名称：

  溴juglone衍生物的区域特异性合成

  摘要：

  N-溴代琥珀酰亚胺与1,5-和1,8-二乙酰氧基萘。

  DOI：

  10.1016/s0040-4039(00)77843-9
• 作为产物：
  描述：

  以 乙酸酐 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 1,8-diacetoxynaphthalene
  参考文献：
  名称：

  Conversion of N-Aromatic Amides to O-Aromatic Esters

  摘要：

  [GRAPHICS]N-Aromatic secondary amides can be transformed into O-aromatic esters in high yield via N-nitrosamide intermediates. The amides can be generated in situ from the corresponding aromatic amines or nitro compounds, and phenols can easily be made from the esters. The reaction can be modified by addition of methyl methacrylate or toluene at 0 degreesC to give polymerization or deamination, respectively. The rearrangement mechanism may involve radical formation and recombination.

  DOI：

  10.1021/ol026051d

文献信息

• Kinetics of hydrolysis of 1-acetoxy-, 1-acetoxy-8-hydroxy-, and 1,8-diacetoxy-napthalenes; intramolecular participation by a hydroxy group
  作者：Frank Hibbert、Karen J. Spiers

  DOI：10.1039/p29880000571

  日期：——

  Consecutive hydrolysis of the acetoxy groups in 1,8-diacetoxynaphthalene in aqueous alkaline solution can be studied kinetically because hydrolysis occurs more rapidly for the diacetate than for 1-acetoxy-8-hydroxynaphthalene which is mostly present in the ionised form. The dependence of the rate coefficient (k2) for hydrolysis of 1-acetoxy-8-hydroxynaphthalene on the concentration of hydroxide ion

  可以从动力学上研究碱性水溶液中1,8-二乙酰氧基萘中乙酰氧基的连续水解，因为二乙酸酯的水解比1-乙酰氧基-8-羟基萘的水解更快，后者主要以离子化形式存在。1-乙酰氧基-8-羟基萘水解的速率系数（k 2）对氢氧根离子浓度的依赖性很复杂，因为电离和非电离形式之间的平衡以及它们的不同反应性。的电离和未电离形式之间的平衡已被分别测量和数据与动力学结果相结合，以显示，该线性关系ķ 2上[OH -]在高浓度是由于与OH的离子化形式的反应- 。在低浓度，的弯曲依赖性ķ 2的[OH - ]可通过电离1-乙酸基-8-羟基萘与溶剂的反应进行说明。与1-乙酰氧基萘与水反应的值相比，该反应的速率系数（k 4）的值表明羟基通过分子内一般碱催化来辅助水的攻击。观察到动力学溶剂同位素效应k 4（H 2 O）/ k 4（D 2 O）2.2±0.5。
• Film for optical elements
  申请人：Nippon Mitsubishi Oil Corporation

  公开号：EP0982621A2

  公开（公告）日：2000-03-01

  A film for optical elements is formed by a liquid crystalline composition comprising the following components (a) and (b): (a) a liquid crystalline polymer which exhibits an optically positive uniaxial property; and (b) a polycyclic compound having a molecular weight of not more than 1,000 and wherein a plurality of alicyclic rings and/or aromatic rings are connected together through a linkage chain of 0 to 4 main-chain carbon atoms bonded to different ring carbon atoms, with hydrocarbon groups each having 1 to 20 carbon atoms being bonded respectively to both end rings through a linkage chain of 0 to 4 main-chain carbon atoms,    an orientation form formed in the state of liquid crystal of said liquid crystalline composition being fixed.

  用于光学元件的薄膜由液晶组合物形成，液晶组合物包括以下成分 (a) 和 (b)： (a) 具有光学正单轴性的液晶聚合物；和 (b) 多环化合物，其分子量不超过 1,000，其中多个脂环和/或芳香环通过 0 至 4 个主链碳原子的连接链连接在一起，这些主链碳原子与不同的环碳原子键合，而每个具有 1 至 20 个碳原子的烃基通过 0 至 4 个主链碳原子的连接链分别与两个端环键合、 所述液晶组合物在液晶状态下形成的取向形式是固定的。
• Leveraging Nonstrained C–C Bonds for Selective Carboacylation of an Unactivated Alkyne via Transient Dearomatization
  作者：Jiamin He、Tongxiang Cao、Kai Chen、Shifa Zhu

  DOI：10.1021/acs.orglett.4c00608

  日期：2024.4.5

  Carboacylation of an unsaturated bond represents a powerful transformation. However, only a few examples of carboacylation of alkyne have been reported through C–C bond scission and reconnection. Here, we report a method of carboacylation of an unactivated alkyne by utilizing nonstrained C–C bonds under gold(I) catalysis. The density functional theory computational and experimental studies reveal that

  不饱和键的碳酰化代表了强大的转变。然而，仅报道了少数通过C-C键断裂和重新连接进行炔烃碳酰化的例子。在这里，我们报道了一种在金（I）催化下利用非张力 C-C 键对未活化的炔烃进行碳酰化的方法。密度泛函理论计算和实验研究表明，该反应通过溶剂笼嵌套酰基阳离子从 C 到 C 的形式 1,3-酰基迁移进行。
• Green, Journal of the Chemical Society, 1927, p. 2343
  作者：Green

  DOI：——

  日期：——
• The formal oxidative addition of electron-rich transoid dienes to bromonaphthoquinones
  作者：John R. Grunwell、Anastas Karipides、Carl T. Wigal、Stephen W. Heinzman、John Parlow、Joan A. Surso、Laura Clayton、Fred J. Fleitz、Martin Daffner、Jonathan E. Stevens

  DOI：10.1021/jo00001a020

  日期：1991.1

  This work established the idea that a halogen atom, such as bromine, will act as a control element in the regiospecific formation of a new carbon-carbon bond. The addition of the electron-rich end of a transoid diene to a bromojuglone derivative occurred exclusively at the unsubstituted carbon of the quinone. Thus, 2,2-dimethyl-4-methoxy-6-methylene-1,3-dioxa-2-sila-4-cyclohexene (3) and either 2- or 3-bromo-5-hydroxy-1,4-naphthoquinone (1 or 2) afforded the adducts 19 or 20 in 57% or 71% yield. Similarly, 2,2-dimethyl-6-methylene-4-(trimethylsiloxy)-1,3-diox-4-ene (4) and 1 gave 21 in 77% yield.

表征谱图