2-(1-adamantyloxy)ethyl acrylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(1-adamantyloxy)ethyl acrylate
• 英文别名: 2-(1-Adamantyloxy)ethyl prop-2-enoate；2-(1-adamantyloxy)ethyl prop-2-enoate
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: TVKWDMLKVVVMPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-adamantyloxy)ethyl acrylate 在 盐酸 、 三乙胺 、 tin(ll) chloride 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.67h， 生成 2-(1-adamantyloxy)ethyl 5-[hydroxy(tetrahydrofuran-2-yl)amino]isoxazole-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 5-hydroxylaminoisoxazole derivatives as lipoxygenase inhibitors and metabolism enhancing agents

  摘要：

  A versatile synthesis of novel 5-hydroxylaminoisoxazoles bearing adamantane moieties has been accomplished using the heterocyclization reactions of readily available unsaturated esters by the treatment with tetranitromethane in the presence of triethylamine and subsequent reduction of resulting 5-nitroisoxazoles by SnCl2 with the participation of THF. A number of obtained isoxazole derivatives were evaluated for their antioxidative activity, inhibition of lipoxygenases and impact on the rat liver mitochondria. The majority of tested compounds demonstrated moderate antiradical activity in DPPH test (up to EC50 16 mu M). The same compounds strongly inhibited soybean lipoxygenase (up to IC50 0.4 mu M) and Fe2+- and Fe3+-induced lipid peroxidation (LP) of rat brain cortex homogenate (up to IC50 0.3 mu M). All tested isoxazole derivatives promoted the phosphorylating respiratory activity simultaneously with maximal stimulated respiratory activity of mitochondria and do not reveal any toxicity towards the primary culture of rat cortex neurons. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.12.040
• 作为产物：
  描述：

  1-(2-Hydroxy-ethoxy)-adamantan 、 丙烯酰氯 以 二氯甲烷 为溶剂， 以72%的产率得到2-(1-adamantyloxy)ethyl acrylate
  参考文献：
  名称：

  基于异恶唑核心与金刚烷连接的传播的黄病毒繁殖抑制剂。

  摘要：

  黄病毒引起的感染对全世界的公共卫生构成了巨大的威胁。寻找靶向tick传播的黄病毒的治疗相关化合物需要探索新的化学型。在本工作中，通过我们独特的通用合成方法，获得了一系列具有多种空间和电子效应的带有取代基的新型多官能化异恶唑衍生物，并在体外研究了它们对壁虱传播性脑炎，鄂木斯克出血热和Powassan病毒的抗病毒活性。大多数研究的异恶唑显示出低微摩尔范围的活性。对于测试的化合物未观察到明显的细胞毒性。含金刚烷基部分的先导化合物5-氨基异恶唑衍生物具有很强的抗病毒活性和极好的治疗指数。

  DOI：

  10.1016/j.bioorg.2019.03.028

文献信息

• CURABLE RESIN COMPOSITION AND MOLDED ARTICLE
  申请人：FUJIFILM Corporation

  公开号：US20130131212A1

  公开（公告）日：2013-05-23

  Disclosed is a curable resin composition comprising a polymer (A) that has a main chain comprising carbon atoms and a side chain having a polymerizing unsaturated linking group and has a cyclic structure in the main chain and/or the side chain, and a compound having a polymerizing unsaturated group. The curable resin composition has good optical characteristics, good heat resistance and good moldability.
• PHOTORESIST TOPCOAT COMPOSITIONS AND METHODS OF PROCESSING PHOTORESIST COMPOSITIONS
  申请人：Rohm and Haas Electronic Materials LLC

  公开号：US20190204741A1

  公开（公告）日：2019-07-04

  Photoresist topcoat compositions comprise: an aqueous base soluble polymer comprising as polymerized units a monomer of the following general formula (I): wherein: R 1 is chosen from H, halogen atom, C1-C3 alkyl, or C1-C3 haloalkyl; R 2 is independently chosen from substituted or unsubstituted C1-C12 alkyl or substituted or unsubstituted C5-C18 aryl; R3 and R4 are independently H, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C5-C18 aryl; X is a C2-C6 substituted or unsubstituted alkylene group; wherein X can optionally comprise one or more rings and together with R 2 can optionally form a ring; L 1 is a single bond or a linking group; p is an integer of from 1 to 50; and q is an integer of from 1 to 5; and a solvent. Substrates coated with the described topcoat compositions and methods of processing a photoresist composition are also provided. The invention finds particular applicability in the manufacture of semiconductor devices.
• US8822563B2
  申请人：——

  公开号：US8822563B2

  公开（公告）日：2014-09-02
• Synthesis and biological evaluation of novel 5-hydroxylaminoisoxazole derivatives as lipoxygenase inhibitors and metabolism enhancing agents
  作者：Elena B. Averina、Dmitry A. Vasilenko、Yulia A. Gracheva、Yuri K. Grishin、Eugene V. Radchenko、Vladimir V. Burmistrov、Gennady M. Butov、Margarita E. Neganova、Tatyana P. Serkova、Olga M. Redkozubova、Elena F. Shevtsova、Elena R. Milaeva、Tamara S. Kuznetsova、Nikolay S. Zefirov

  DOI：10.1016/j.bmc.2015.12.040

  日期：2016.2

  A versatile synthesis of novel 5-hydroxylaminoisoxazoles bearing adamantane moieties has been accomplished using the heterocyclization reactions of readily available unsaturated esters by the treatment with tetranitromethane in the presence of triethylamine and subsequent reduction of resulting 5-nitroisoxazoles by SnCl2 with the participation of THF. A number of obtained isoxazole derivatives were evaluated for their antioxidative activity, inhibition of lipoxygenases and impact on the rat liver mitochondria. The majority of tested compounds demonstrated moderate antiradical activity in DPPH test (up to EC50 16 mu M). The same compounds strongly inhibited soybean lipoxygenase (up to IC50 0.4 mu M) and Fe2+- and Fe3+-induced lipid peroxidation (LP) of rat brain cortex homogenate (up to IC50 0.3 mu M). All tested isoxazole derivatives promoted the phosphorylating respiratory activity simultaneously with maximal stimulated respiratory activity of mitochondria and do not reveal any toxicity towards the primary culture of rat cortex neurons. (c) 2015 Elsevier Ltd. All rights reserved.
• Tick-borne flavivirus reproduction inhibitors based on isoxazole core linked with adamantane
  作者：Dmitry A. Vasilenko、Evgenia V. Dueva、Liubov I. Kozlovskaya、Nikolay A. Zefirov、Yuri K. Grishin、Gennady M. Butov、Vladimir A. Palyulin、Tamara S. Kuznetsova、Galina G. Karganova、Olga N. Zefirova、Dmitry I. Osolodkin、Elena B. Averina

  DOI：10.1016/j.bioorg.2019.03.028

  日期：2019.6

  Infections caused by flaviviruses pose a huge threat for public health all over the world. The search for therapeutically relevant compounds targeting tick-borne flaviviruses requires the exploration of novel chemotypes. In the present work a large series of novel polyfunctionalized isoxazole derivatives bearing substituents with various steric and electronic effects was obtained by our unique versatile

  黄病毒引起的感染对全世界的公共卫生构成了巨大的威胁。寻找靶向tick传播的黄病毒的治疗相关化合物需要探索新的化学型。在本工作中，通过我们独特的通用合成方法，获得了一系列具有多种空间和电子效应的带有取代基的新型多官能化异恶唑衍生物，并在体外研究了它们对壁虱传播性脑炎，鄂木斯克出血热和Powassan病毒的抗病毒活性。大多数研究的异恶唑显示出低微摩尔范围的活性。对于测试的化合物未观察到明显的细胞毒性。含金刚烷基部分的先导化合物5-氨基异恶唑衍生物具有很强的抗病毒活性和极好的治疗指数。