acetic acid 2-(3-hydroxyphenyl)ethyl ester | 151287-95-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: acetic acid 2-(3-hydroxyphenyl)ethyl ester
• 英文别名: 2-(3-Hydroxyphenyl)ethyl acetate；2-(3-hydroxyphenyl)ethyl acetate
• CAS: 151287-95-5
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: RBRVVGIKZZPRJY-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：

  acetic acid 2-(3-hydroxyphenyl)ethyl ester 在 甲醇 、 硝基乙烷 、 乙基溴化镁 、 sodium acetate 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 21.5h， 生成 benzenesulfonic acid 3-[2-(3-allyloxy-4-cyanophenyl)ethoxy]phenyl ester
  参考文献：
  名称：

  Statistical Molecular Design, Parallel Synthesis, and Biological Evaluation of a Library of Thrombin Inhibitors

  摘要：

  A library of thrombin inhibitors has been designed using statistical molecular design. An aromatic scaffold was used, with three varied positions corresponding to three pockets at the active site of thrombin (the S-, P-, and D-pockets). The selection was performed in the building block space, and previously acquired data were included in the design procedure. The design resulted in six, four, and six building blocks for the first (S), second (P), and third (D) pockets, respectively. A second round of selection applied to the combined selected building blocks resulted in a subset of 18 compounds. The selected library was synthesized in parallel and biologically evaluated. The compounds were analyzed with respect to their inhibition (pIC(50)) of thrombin; membrane permeability, estimated by migration behavior in micellar media (CE log k') and pK(a); and specificity with respect to inhibition (K-i) of trypsin. Multivariate QSAR studies of the responses yielded valuable results and information that could only be found using statistical molecular design in combination with multivariate analysis.

  DOI：

  10.1021/jm010833f
• 作为产物：
  描述：

  Diacetyl-1,3-tyrosol 在 phosphate buffer 、 Pseudomonas cepacia PS lipase 作用下， 以 丙酮 为溶剂， 反应 0.08h， 生成 acetic acid 2-(3-hydroxyphenyl)ethyl ester
  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

• Alkylchlorotins Grafted to Cross-Linked Polystyrene Beads by a ?(CH2)n? Spacer (n=4, 6, 11): Selective, Clean and Recyclable Catalysts for Transesterification Reactions
  作者：Carlos Camacho-Camacho、Monique Biesemans、Manu Van Poeck、Fr�d�ric A. G. Mercier、Rudolph Willem、Karine Darriet-Jambert、Bernard Jousseaume、Thierry Toupance、Uwe Schneider、Ursula Gerigk

  DOI：10.1002/chem.200400999

  日期：2005.4.8

  Insoluble polystyrene grafted compounds of the type (P-H)(1-t)P-(CH2)n SnBu(p)Cl(3-p)}(t), (P-H)(1-t)P-(CH2)n SnBuO}(t) and (P-H)(1-t)[P-(CH2)n SnBuCl}2O](t/2), in which (P-H) is a cross-linked polystyrene; n=4, 6, and 11; p=0 and 1; and t the degree of functionalisation, were synthesised from Amberlite XE-305, a polystyrene cross-linked with divinylbenzene. The compounds were characterised by using

  （PH）（1-t）P-（CH2）n SnBu（p）Cl（3-p）}（t），（PH）（1-t）P-（CH2 ）n SnBuO}（t）和（PH）（1-t）[P-（CH2）n SnBuCl} 2O]（t / 2），其中（PH）是交联的聚苯乙烯；n = 4、6和11；p = 0和1；以及官能度是由与二乙烯基苯交联的聚苯乙烯Amberlite XE-305合成的。通过使用元素分析，IR，拉曼，固态117Sn NMR以及1H和119Sn高分辨率MAS NMR光谱对化合物进行表征。在乙酸乙酯与各种醇的酯交换反应中评估了间隔物长度和锡官能度对这些化合物的催化活性及其再循环能力的影响。这些研究表明，根据催化中心迁移率的变化，催化剂的活性存在显着差异。某些负载型催化剂可以循环使用至少7次，而活性没有明显下降。发现反应产物中的残留锡含量低至3ppm。
• Statistical Molecular Design, Parallel Synthesis, and Biological Evaluation of a Library of Thrombin Inhibitors
  作者：Anna Linusson、Johan Gottfries、Thomas Olsson、Eivor Örnskov、Staffan Folestad、Bo Nordén、Svante Wold

  DOI：10.1021/jm010833f

  日期：2001.10.1

  A library of thrombin inhibitors has been designed using statistical molecular design. An aromatic scaffold was used, with three varied positions corresponding to three pockets at the active site of thrombin (the S-, P-, and D-pockets). The selection was performed in the building block space, and previously acquired data were included in the design procedure. The design resulted in six, four, and six building blocks for the first (S), second (P), and third (D) pockets, respectively. A second round of selection applied to the combined selected building blocks resulted in a subset of 18 compounds. The selected library was synthesized in parallel and biologically evaluated. The compounds were analyzed with respect to their inhibition (pIC(50)) of thrombin; membrane permeability, estimated by migration behavior in micellar media (CE log k') and pK(a); and specificity with respect to inhibition (K-i) of trypsin. Multivariate QSAR studies of the responses yielded valuable results and information that could only be found using statistical molecular design in combination with multivariate analysis.
• 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。