2-(acetoxy)-5-methoxyphenyl acetate | 82822-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-(acetoxy)-5-methoxyphenyl acetate
• 英文别名: 4-methoxy-1,2-phenylene diacetate；4-methoxyphenylene-1,2-diacetate；catechol diacetate；1,2-diacetoxy-4-methoxy-benzene；(4-Methoxy-o-phenylen)-diacetat；1,2-Diacetoxy-4-methoxy-benzol；(2-Acetyloxy-4-methoxyphenyl) acetate
• CAS: 82822-28-4
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: PUOYFDLLYBPILR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Ditert-butyl-hydroxy-(4-methoxyphenoxy)silane 在 吡啶 、 Pd(opiv)2 、 碘苯二乙酸 作用下， 以 甲苯 为溶剂， 生成 2-(acetoxy)-5-methoxyphenyl acetate
  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

• Efficient <i>ortho</i>-Oxidation of Phenols with Diacyl Peroxides
  作者：Masahiro Tada、Risa Ishiguro、Ryohei Izumi

  DOI：10.1248/cpb.56.239

  日期：——

  A stable symmetric diacyl peroxide, m-chlorobenzoyl peroxide (mCBPO), and an asymmetric diacyl peroxide, chloroacetyl m-chlorobenzoyl peroxide (CAMCBPO), were synthesized from m-chloroperbenzoic acid. Both peroxides oxidized phenols selectively at the ortho position predoninantly. CAMCBPO gave para-oxidized compounds as minor products from some phenols. The improvement of the yield of ortho-oxidation of phenols with mCBPO was also reported.

  从间氯过苯甲酸出发，合成了稳定的对称二酰基过氧化物间氯苯甲酰过氧化物（mCBPO）和非对称二酰基过氧化物氯乙酰基间氯苯甲酰过氧化物（CAMCBPO）。这两种过氧化物主要选择性地在苯酚的邻位进行氧化。从某些苯酚出发，CAMCBPO得到了少量对位氧化产物。还报道了使用mCBPO提高苯酚邻位氧化产率的方法。
• An Optical Method for the Study of Reversible Organic Oxidation—Reduction Systems. V. o-Benzoquinones
  作者：D. E. Kvalnes

  DOI：10.1021/ja01326a085

  日期：1934.11
• Electrophilic components in the electrochemical acetoxylation of substituted arenes
  作者：Alexander V. Burasov、Vladimir A. Petrosyan

  DOI：10.1016/j.mencom.2008.07.008

  日期：2008.7

  The mechanism of anodic acetoxylation of substituted arenes under conditions of undivided galvanostatic electrolysis in MeCN containing acetate is suggested and an important role of electrophilic components (AcOH or ZnCl2) catalyzing transformation of intermediate ipso-acetoxylated polysubstituted arenonium cations to corresponding ortho-acetoxylated arenonium cations, which give acetoxylation products after deprotonation, is experimentally proved.
• Regioselective Oxidation of Phenols to <i>o</i>-Quinones with <i>o</i>-Iodoxybenzoic Acid (IBX)
  作者：Derek Magdziak、Andy A. Rodriguez、Ryan W. Van De Water、Thomas R. R. Pettus

  DOI：10.1021/ol017068j

  日期：2002.1.1

  GRAPHICSAn efficient regioselective method for oxidation of phenols to o-quinones is reported. When this procedure is combined with a subsequent reduction, it proves to be useful for the construction of a variety of catechols.
• MIYAJIMA, MASAHIRO, J. ASAHIKAWA TECHN. COLL., 1982, N 19, 129-136
  作者：MIYAJIMA, MASAHIRO

  DOI：——

  日期：——