4-acetoxymethyl-2-methoxyphenol | 57404-55-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-acetoxymethyl-2-methoxyphenol
• 英文别名: 4-hydroxy-3-methoxybenzyl ethanoate；(4-hydroxy-3-methoxyphenyl)methyl acetate
• CAS: 57404-55-4
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: DZWDEGBGKYCSKL-UHFFFAOYSA-N

物化性质

• 熔点：
  139.5-140.5 °C
• 沸点：
  304.2±27.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)
• 保留指数：
  1677

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-acetoxymethyl-2-methoxyphenol 在 甲醇 、 Novozym 435 、 sodium methylate 、 magnesium sulfate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 丙酮 、 甲苯 为溶剂， 反应 20.0h， 生成 O-[4-(β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyloxy)-3-methoxybenzyl]-n-hexanoic acid ester
  参考文献：
  名称：

  GLYCOSIDE COMPOUND

  摘要：

  式（I″）的化合物 其中： R11，R12，R13，R14和R15为氢，羟基，C1-6烷基，C1-6烷氧基，C1-6烷基羰氧基或G-O-基团，且R11，R12，R13，R14和R15中至少有一个是G-O-基团，其中G是糖残基， X1是单键，或亚甲基基团，乙烯基团，三亚甲基基团，乙烯基团或-CH=CH-CH2-， X2是-CO-O-或-O-CO-， p和q是0到7的整数，且p+q=0到8， Y1是亚甲基，乙烯基或碳数为2到15且具有1到3个双键的烯基基团，以及 R16和R17为氢，甲基或乙基，或R16和R17形成C3-6环烷基基团，可用作GLP-1分泌促进剂。

  公开号：

  US20130288992A1
• 作为产物：
  描述：

  4-acetoxymethyl-2-methoxyphenyl acetate 在 Candida rugosa lipase (CRL, Type II) 作用下， 以 异丙醚 、 正丁醇 为溶剂， 反应 288.0h， 以50%的产率得到4-acetoxymethyl-2-methoxyphenol
  参考文献：
  名称：

  Enzyme-Catalyzed Chemoselective Transesterification Reactions on Hydroxymethylated Phenolic Compounds

  摘要：

  The chemoselective capabilities of porcine pancreatic lipase (PPL) in tetrahydrofuran and Candida rugosa lipase (CRL) in diisopropyl ether have been investigated for selective acetylation and deacetylation of hydroxymethylated phenols and hydroxyaryl alkyl ketones and their peracetylated derivatives. Both PPL and CRL exhibited exclusive selectivity for the acetylation of alcoholic hydroxyl group over the phenolic hydroxyl group(s) of the hydroxymethylated phenols 1-5 and aryl alkyl ketones 6-9, and for the deacetylation of ester group involving the phenolic hydroxyl group over the ester group involving alcoholic hydroxyl of the peracetates 19-24. The preliminary results indicate that this strategy of chemoselective acetylation can also be used in the enantiomeric resolution of racemic ketones 6-9. Single crystal X-ray diffraction studies have confirmed the structures of compounds 4, 15, and 17. (C) 1999 Academic Press.

  DOI：

  10.1006/bioo.1998.1117

文献信息

• Microwave-assisted rapid and efficient deprotection and direct esterification and silylation of MOM and EOM ethers catalyzed by [Hmim][HSO4] as a Brønsted acidic ionic liquid
  作者：Iraj Mohammadpoor-Baltork、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani、Ahmad Reza Khosropour、Arsalan Mirjafari

  DOI：10.1007/s00706-010-0373-6

  日期：2010.10

  Abstract1-Methylimidazolium hydrogensulfate, [Hmim][HSO4], a Brønsted acidic room temperature ionic liquid, is used as a catalyst and reaction medium for facile and eco-friendly deprotection of methoxymethyl (MOM) and ethoxymethyl (EOM) ethers to their corresponding alcohols under thermal conditions (Δ) and microwave irradiation (MW). Furthermore, one-pot interconversion to the respective acetates and

  摘要布朗斯台德酸性室温离子液体1-甲基咪唑硫酸氢盐[Hmim] [HSO 4 ]被用作催化剂和反应介质，可对甲氧基甲基（MOM）和乙氧基甲基（EOM）醚进行简便且环保的脱保护醇在热条件（Δ）和微波辐射（MW）下。此外，还实现了一锅转化为各自的乙酸酯和三甲基甲硅烷基（TMS）醚。 图形概要
• Chemoselective CaO-Mediated Acylation of Alcohols and Amines in 2-Methyltetrahydrofuran
  作者：Vittorio Pace、Pilar Hoyos、Andrés R. Alcántara、Wolfgang Holzer

  DOI：10.1002/cssc.201200922

  日期：2013.5

  Calcium oxide is proposed as an innocuous acid scavenger for the chemoselective synthesis of amide‐ and ester‐type compounds. Although these molecules have wide spread applications in organic and pharmaceutical chemistry, and a large number of routes have been designed for their synthesis, the development of more efficient and environmentally friendly acylation strategies remains an ongoing challenge

  氧化钙被提议作为酰胺和酯类化合物化学选择性合成的无害酸清除剂。尽管这些分子在有机和药物化学中具有广泛的应用，并且已经设计了许多合成途径，但是开发更有效和对环境友好的酰化策略仍然是一项持续的挑战。CaO的使用允许在酚或叔醇存在下伯醇的化学计量酰化；胺还可以在羟基存在下进行酰化反应。如果起始原料是光学纯的醇或使用手性酰化剂，则通过酰化获得手性。此外，使用更环保的溶剂2-甲基四氢呋喃（2-MeTHF），导致产量最大化。该协议已成功应用于有趣的综合N-芳基恶唑烷-2-酮中间体，用于制备利奈唑胺类化合物。
• Application of Hansch’s Model to Capsaicinoids and Capsinoids: A Study Using the Quantitative Structure−Activity Relationship. A Novel Method for the Synthesis of Capsinoids
  作者：Gerardo F. Barbero、José M. G. Molinillo、Rosa M. Varela、Miguel Palma、Francisco A. Macías、Carmelo G. Barroso

  DOI：10.1021/jf9035029

  日期：2010.3.24

  been synthesized, and a new method for the synthesis of these compounds has been developed. The yields range from 48.35 to 98.98%. It has been found that the synthetic capsaicinoids and capsinoids present a lipophilia similar to those of the natural compounds and present similar biological activity. The bioactivity of the synthetic capsaicinoids and capsinoids decreases proportionally to the degree of

  作为结构和活性之间定量关系研究的一部分，我们描述了两种类化合物的合成方法：辣椒素和辣椒素。总共合成了14个增加的侧链长度（从2到16个碳原子）的辣椒素。另外，已经合成了14个具有相同侧链的辣椒素以及衣壳和二氢衣壳，并且已经开发了用于合成这些化合物的新方法。产率为48.35至98.98％。已经发现，合成的辣椒素类和辣椒素类具有与天然化合物相似的亲脂性，并具有相似的生物学活性。与天然化合物相比，合成辣椒素和辣椒素的生物活性与亲脂性差异程度（较高或较低）成比例地降低。使用黄化的小麦测定生物活性（小麦胚芽鞘生物测定法，并通过将合成结果与其对应的天然化合物呈现的结果进行比较。发现的生物活性与合成化合物的亲脂性直接相关。
• Lipase-catalysed chemoselective monoacetylation of hydroxyalkylphenols and chemoselective removal of a single acetyl group from their diacetates
  作者：Pietro Allevi、Pierangela Ciuffreda、Alessandra Longo、Mario Anastasia

  DOI：10.1016/s0957-4166(98)00285-7

  日期：1998.8

  It was demonstrated that Pseudomonas cepacia PS lipase adsorbed on Celite, has the ability to catalyse the chemoselective monoacetylation of various hydroxyalkylphenols or the chemoselective removal of a single acetyl group from the corresponding acetate.

  已证明，吸附在硅藻土上的洋葱假单胞菌PS脂肪酶具有催化各种羟烷基酚的化学选择性单乙酰化或从相应的乙酸盐中化学选择去除单个乙酰基的能力。
• An efficient method for selective acetylation of alcoholic hydroxyl groups.
  作者：YOSHIMITSU NAGAO、EIICHI FUJITA、TATSUHIKO KOHNO、MASAHIRO YAGI

  DOI：10.1248/cpb.29.3202

  日期：——

  Acetylation of the C-6 hydroxyl group in oridonin (1), which is difficult by the use of acetic anhydride in pyridine, was investigated using acetic anhydride in the presence of some Lewis acids. A reagent system of acetic anhydride in the presence of a catalytic amount of boron trifluoride etherate was shown to be effective for this purpose. This reagent system was shown to be useful for selective acetylation of the alcoholic group (s) in compounds which have both alcoholic and phenolic hydroxyl groups.

  研究人员在一些路易斯酸存在的情况下，使用醋酸酐对奥里多宁（1）中的 C-6 羟基进行了乙酰化反应。结果表明，在催化量的三氟化硼醚酸存在下的醋酸酐试剂体系可以有效地实现这一目的。这种试剂体系对具有醇羟基和酚羟基的化合物中醇羟基的选择性乙酰化非常有用。