3-(4'-hydroxyphenyl)-1-propyl acetate | 80373-18-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(4'-hydroxyphenyl)-1-propyl acetate
• 英文别名: 3-(4-hydroxyphenyl)propyl acetate；3-(4-hydroxyphenyl)propanacetate；4-(3-acetoxypropyl)phenol
• CAS: 80373-18-8
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: UARIKUWXCSCJBL-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）
• LogP：
  2.193 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4'-hydroxyphenyl)-1-propyl acetate 在 2-碘酰基苯甲酸 、 sodium dithionite 作用下， 以 甲醇 、 水 为溶剂， 反应 1.08h， 生成 3-(3,4-dihydroxyphenyl)propyl acetate
  参考文献：
  名称：

  Synthesis and Structure/Antioxidant Activity Relationship of Novel Catecholic Antioxidant Structural Analogues to Hydroxytyrosol and Its Lipophilic Esters

  摘要：

  A large panel of novel catecholic antioxidants and their fatty acid or methyl carbonate esters has been synthesized in satisfactory to good yields through a 2-iodoxybenzoic acid (IBX)-mediated aromatic hydroxylation as the key step. The new catechols are structural analogues of naturally occurring hydroxytyrosol (3,4-DHE). To evaluate structure/activity relationships, the antioxidant properties of all catecholic compounds were evaluated in vitro by ABTS assay and on whole cells by DCF fluorometric assay and compared with that of the corresponding already known hydroxytyrosyl derivatives. Results outline that all of the new catechols show antioxidant capacity in vitro higher than that of the corresponding hydroxytyrosyl derivatives. Less evident positive effects have been detected in whole cells experiments. Cytotoxicity experiments, using MTT assay, on a representative set of compounds evidenced no influence in cell survival.

  DOI：

  10.1021/jf301131a
• 作为产物：
  描述：

  对羟基苯丙酸 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 lithium aluminium tetrahydride 、 氢气 、 氢气 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 乙酸乙酯 、 苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 3-(4'-hydroxyphenyl)-1-propyl acetate
  参考文献：
  名称：

  Krawczyk, Andrzej R.; Lipkowska, Ewa; Wrobel, Jerzy T., Bulletin of the Polish Academy of Sciences: Chemistry, 1986, vol. 34, # 3-4, p. 115 - 122

  摘要：

  DOI：

文献信息

• SELECTIVE ACETYLATION OF ALIPHATIC HYDROXYL GROUP IN THE PRESENCE OF PHENOLIC HYDROXYL GROUP USING SILICA GEL SUPPORTED BF₃CATALYST
  作者：Biswanath Das、B. Venkataiah、P. Madhusudhan

  DOI：10.1081/scc-120002009

  日期：2002.1

  ABSTRACT Selective acetylation of aliphatic hydroxyl group in the presence of phenolic hydroxyl group was achieved conveniently and efficiently by treatment with EtOAc in the presence of silica gel supported BF3 catalyst.

  摘要 通过在硅胶负载的 BF3 催化剂存在下用 EtOAc 处理，可以方便有效地实现在酚羟基存在下脂肪族羟基的选择性乙酰化。
• Selective acylation of aliphatic alcohols in the presence of phenolic hydroxyl groups
  作者：Gowravaram Sabitha、Basi V. Subba Reddy、Garudammagari S. Kiran Kumar Reddy、Jhillu S. Yadav

  DOI：10.1039/a908235b

  日期：——

  A new and efficient method for the selective acylation of aliphatic hydroxyl groups in the presence of phenolic groups using a mixture of trimethyl orthoacetate and trimethylsilyl chloride at room temperature is reported. The reactions are selective, high yielding and complete within 3–6 h.

  报道了在室温下使用三乙酸原乙酸酯和三甲基甲硅烷基氯的混合物在酚基存在下选择性脂肪酰化的一种新的有效方法。反应具有选择性，高收率，并在3-6小时内完成。
• Selective acylation of a sterically hindered hydroxyl group of unsymmetrical diols containing a primary hydroxyl group such as 1,5-hexanediol in the presence of silica gel with acetyl chloride
  作者：Haruo Ogawa、Yuko Ide、Ryoichi Honda、Teiji Chihara

  DOI：10.1002/poc.622

  日期：2003.6

  selectively formed in the presence of silica gel with acetyl chloride by refluxing a suspension of unsymmetrical diols containing a primary hydroxyl group such as 1,5-hexanediol preadsorbed on silica gel. Such regioselectivity was observed through preferential adsorption via a primary hydroxyl group of the diols. Copyright © 2003 John Wiley & Sons, Ltd.

  在硅胶与乙酰氯的存在下，通过回流预吸附在硅胶上的含伯羟基的不对称二醇（如1,5-己二醇）的悬浮液，选择性地形成受阻更大的单乙酸酯。通过经由二醇的伯羟基的优先吸附观察到这种区域选择性。版权所有©2003 John Wiley＆Sons，Ltd.
• Organic reactions at alumina surfaces. An extremely simple, convenient and selective method for acetylating primary alcohols in the presence of secondary alcohols.
  作者：Gary H. Posner、Mitsunori Oda

  DOI：10.1016/s0040-4039(01)92404-9

  日期：1981.1

  Stirring primary-secondary diols in ethyl acetate solvent over Woelm alumina leads to the corresponding primary monoacetates simply, conveniently, and in good yields. In this way, primary hydroxyalkylphenols are converted into acetoxyalkylphenols, and primary arylamines are transformed into the corresponding acetamides.

  在Woelm氧化铝上在乙酸乙酯溶剂中搅拌伯-仲二醇可简单，方便且以高收率得到相应的伯单乙酸酯。以这种方式，伯羟烷基苯酚被转化为乙酰氧基烷基苯酚，伯芳基胺被转化为相应的乙酰胺。
• 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。