2-(2-hydroxyphenyl)ethyl acetate | 138459-95-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(2-hydroxyphenyl)ethyl acetate
• 英文别名: 2-(2-acetoxy-ethyl)-phenol；2-Oxy-1²-acetoxy-1-aethyl-benzol；2-(2-Acetoxy-aethyl)-phenol
• CAS: 138459-95-7
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: BZGPZFRKDKHUSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxyphenyl)ethyl 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 2-(2,3-Dihydroxyphenyl)ethyl 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：

  Diacetyl-1,2-tyrosol 在 phosphate buffer 、 Pseudomonas cepacia PS lipase 作用下， 以 丙酮 为溶剂， 反应 0.17h， 生成 2-(2-hydroxyphenyl)ethyl acetate
  参考文献：
  名称：

  脂肪酶催化羟烷基酚的化学选择性单乙酰化，并从其二乙酸酯化学选择性去除单个乙酰基

  摘要：

  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。

  DOI：

  10.1016/s0957-4166(98)00285-7

文献信息

• Second-GenerationcycloSal-d4TMP Pronucleotides Bearing Esterase-Cleavable Sites — The “Trapping” Concept
  作者：Chris Meier、Christian Ducho、Henning Jessen、Dalibor Vukadinović-Tenter、Jan Balzarini

  DOI：10.1002/ejoc.200500490

  日期：2006.1

  An extension of the cycloSal-pronucleotide approach is presented. Attachment of an enzyme-cleavable ester/acylal group to the cycloSal-d4TMP triesters should allow these compounds to be trapped intracellularly after cleavage. The ester/acylal groups were introduced in the 3- or 5-position of the cycloSal ring system, and surprising differences were observed in hydrolysis studies in CEM cell extracts

  介绍了 cycloSal-核苷酸方法的扩展。将酶可裂解的酯/酰基基团连接到 cycloSal-d4TMP 三酯上应该允许这些化合物在裂解后被捕获在细胞内。在环Sal环系统的3-或5-位引入酯/酰基基团，并且在CEM细胞提取物的水解研究中观察到关于酯/酰基部分的惊人差异。虽然乙酰基酯和乙酰丙酸酯很容易裂解，但 cycloSal-d4TMP 酸的烷基酯证明对酶促裂解具有抗性。相比之下，AM-、POM- 和 POC-酰基在提取物中迅速裂解，产生 cycloSal-d4TMP 酸。还介绍了化合物对 HIV 的抗病毒活性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• 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。
• Substituted Cyclopentanes Or Cyclopentanones As Therapeutic Agents
  申请人：Old W. David

  公开号：US20080058414A1

  公开（公告）日：2008-03-06

  Novel compounds, and therapeutic methods, compositions and medicament related thereto are disclosed herein.

  本文揭示了新型化合物，以及与之相关的治疗方法、组合物和药物。
• SUBSTITUTED CYCLOPENTANES OR CYCLOPENTANONES AS THERAPEUTIC AGENTS
  申请人：Old W. David

  公开号：US20070265464A1

  公开（公告）日：2007-11-15

  Therapeutic compounds, methods, and compositions are disclosed herein.

  这里披露了治疗化合物、方法和组合物。