2,3-naphthalenediol-2,3-diacetate | 22426-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-naphthalenediol-2,3-diacetate
• 英文别名: naphthalene-2,3-diyl diacetate；2,3-diacetoxy-naphthalene；2,3-diacetoxynaphthalene；2,3-Diacetoxy-naphthalin；2,3-Dihydroxy-naphthalin-diacetat；2,3-Diacetoxynaphthalin；2,3-Naphthalenediol diacetate；(3-acetyloxynaphthalen-2-yl) acetate
• CAS: 22426-46-6
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: CNUNETLANGTFDD-UHFFFAOYSA-N

物化性质

• 保留指数：
  1938.4

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：

  2,3-naphthalenediol-2,3-diacetate 在 lipase of Pseudomonas sp 、 水 作用下， 以 various solvent(s) 为溶剂， 反应 14.0h， 生成 2,3-二羟基萘
  参考文献：
  名称：

  假单胞菌（Pseudomonas sp。）催化的对二乙酰氧基萘的区域选择性水解。有机溶剂中的脂肪酶

  摘要：

  取决于芳香环中乙酰基的相对位置，假单胞菌属（Pseudomonas sp。）。脂肪酶催化的二乙酰氧基萘在叔丁基甲基醚中的水解区域选择性地进行，得到相应的单乙酸酯。

  DOI：

  10.1016/s0040-4020(99)01000-5
• 作为产物：
  描述：

  Ditert-butyl-hydroxy-naphthalen-2-yloxysilane 在 吡啶 、 Pd(opiv)2 、 碘苯二乙酸 作用下， 以 三氟甲苯 为溶剂， 生成 2,3-naphthalenediol-2,3-diacetate
  参考文献：
  名称：

  Synthesis of Catechols from Phenols via Pd-Catalyzed Silanol-Directed C–H Oxygenation

  摘要：

  A silanol-directed, Pd-catalyzed C-H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon protected catechol, A routine desilylation of the silacyle With TBAF uncovers the catechol product:

  DOI：

  10.1021/ja208572v

文献信息

• Regioselective Hydrolysis of Diacetoxynaphthalenes Catalyzed by Pseudomonas sp. Lipase in an Organic Solvent
  作者：Pierangela Ciuffreda、Silvana Casati、Enzo Santaniello

  DOI：10.1016/s0040-4020(99)01000-5

  日期：2000.1

  Depending on the relative positions of the acetyl groups in the aromatic rings, the Pseudomonas sp. lipase-catalyzed hydrolysis of diacetoxynaphthalenes in tert-butylmethyl ether proceeds regioselectively to afford the corresponding monoacetates.

  取决于芳香环中乙酰基的相对位置，假单胞菌属（Pseudomonas sp。）。脂肪酶催化的二乙酰氧基萘在叔丁基甲基醚中的水解区域选择性地进行，得到相应的单乙酸酯。
• The first vinyl acetate mediated organocatalytic transesterification of phenols: a step towards sustainability
  作者：Manoj Kumar、Sourav Bagchi、Anuj Sharma

  DOI：10.1039/c5nj01436k

  日期：——

  The present report outlines our efforts toward a simple yet elegant protocol for O-acylation of a wide variety of phenols. This highly enabling and solventless method relies on vinyl acetate as an innocuous acyl donor and DABCO as an organocatalyst. Operational simplicity, excellent yields, higher and faster conversion rates without excess reagents, a simple workup and essentially no need of columns

  本报告概述了我们为简单而优雅的方案进行的各种酚O酰化的努力。这种高度可行且无溶剂的方法依赖于乙酸乙烯酯作为无害的酰基供体，而DABCO作为有机催化剂。操作简便，出众的收率，更高和更快的转化率而无需使用过多的试剂，简单的后处理以及基本上不需要色谱柱，这些都是所报告方案的重要特征。
• Organocatalytic Asymmetric Atroposelective Construction of Axially Chiral 1,4-Distyrene 2,3-Naphthalene Diols
  作者：Shan Li、Da Xu、Fangli Hu、Dongmei Li、Wenling Qin、Hailong Yan

  DOI：10.1021/acs.orglett.8b03398

  日期：2018.12.7

  efficient organocatalytic construction of enantioenriched axially chiral 1,4-distyrene 2,3-naphthalene diols through the nucleophilic addition of α-amido sulfone to in situ generated vinylidene o-quinone methide is described. The reaction pathway was investigated by isolating reaction intermediates and performing a kinetic resolution process. Axially chiral 1,4-distyrene 2,3-naphthalene diol was used as the

  描述了通过亲核加成α-酰胺基砜到原位生成的亚乙烯基邻醌甲基化物中的对映体富集的轴向手性1,4-二苯乙烯2,3-萘二醇的有效有机催化结构。通过分离反应中间体并进行动力学拆分过程来研究反应途径。轴向手性1，4-二苯乙烯2，3-萘二醇用作手性配体，用于将二乙基锌对映选择性地加成到萘甲醛中。初步结果表明，这些加合物可以潜在地用作不对称合成中的配体。
• Studies on Benzochromones. IX. Syntheses of Hydroxyl Derivatives of 2-Methyl-5, 6-benzochromone and 2-Methyl-3-acetyl-5, 6-benzochromone
  作者：Akira Ueno、Seigo Fukushima

  DOI：10.1248/cpb.14.129

  日期：——

  Syntheses of hydroxyl derivatives of 2-methyl-5, 6-bezochromone were investigated, and following benzochromone derivatives were obtained together with related compounds, and physical and chemical properties of these chromones were characterized : 2-Methyl-8-methoxy-5, 6-benzochromone (IV), 2-methyl-7-methoxy-5, 6-benzochromone (X), 2-methyl-7, 8-dimethoxy-5, 6-benzochromone (XIV), 2-methyl-3-acetyl-8-methoxy-5, 6-benzochromone (XXV), 2-methyl-3-acetyl-7-methoxy-5, 6-benzochromone (XXII), and 2-methyl-3-acetyl-7, 8-dimethoxy-5, 6-benzochromone (XXIII). Hydroxylation of 2-methyl-8-hydroxy-5, 6-benzochromone (III) or 2-methyl-7-hydroxy-5, 6-benzochromone (V) gave 2-methyl-7, 8-dihydroxy-5, 6-benzochromone (XX) from both.

  研究了 2-甲基-5, 6-苯并吡喃酮羟基衍生物的合成，得到了以下苯并吡喃酮衍生物及相关化合物，并对这些色酮的物理和化学性质进行了表征：2-Methyl-8-methoxy-5, 6-benzochromone (IV), 2-Methyl-7-methoxy-5, 6-benzochromone (X), 2-Methyl-7, 8-dimethoxy-5, 6-benzochromone (XIV), 2-Methyl-3-acetyl-8-methoxy-5、6-苯并色酮（XXV）、2-甲基-3-乙酰基-7-甲氧基-5，6-苯并色酮（XXII）和 2-甲基-3-乙酰基-7，8-二甲氧基-5，6-苯并色酮（XXIII）。将 2-甲基-8-羟基-5，6-苯并二氢吡喃酮（III）或 2-甲基-7-羟基-5，6-苯并二氢吡喃酮（V）进行羟基化处理，可得到 2-甲基-7，8-二羟基-5，6-苯并二氢吡喃酮（XX）。
• A novel “pro-sensitizer” based sensing of enzymes using Tb(iii) luminescence in a hydrogel matrix
  作者：Sandip Bhowmik、Uday Maitra

  DOI：10.1039/c2cc30904a

  日期：——

  Chemically synthesized “pro-sensitizers” release the sensitizer in the presence of lipase or β-glucosidase, triggering a significant luminescence response from a lanthanide based hydrogel.

  化学合成的 "增感剂 "在脂肪酶或δ-葡萄糖苷酶的作用下释放增感剂，从而引发基于镧系元素的水凝胶产生明显的发光反应。

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