3,5-dimethyl-1-adamantyl acrylate | 23743-72-8

• 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: 3,5-dimethyl-1-adamantyl acrylate
• 英文别名: 1,3-Dimethyl-5-acryloyloxyadamantane；(3,5-dimethyl-1-adamantyl) prop-2-enoate
• CAS: 23743-72-8
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: LCXCLBUJRIUARF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-dimethyl-1-adamantyl 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 3,5-dimethyl-1-adamantyl 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：

  丙烯酸酐 、 3,5-二甲基-1-金刚烷醇 在 Acidic catalyst 作用下， 以 环己烷 为溶剂， 以95%的产率得到3,5-dimethyl-1-adamantyl acrylate
  参考文献：
  名称：

  Otsu, Takayuki; Matsumoto, Akikazu; Horie, Atsushi, Chemistry Letters, 1991, # 7, p. 1145 - 1148

  摘要：

  DOI：

文献信息

• 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。
• Polymerizable adamantane derivatives and process for producing the same
  申请人：Daicel Chemical Industries, Ltd.

  公开号：US06235851B1

  公开（公告）日：2001-05-22

  A compound shown by the following formula: wherein each of R1a, R2a, R3a and R4a represents a substituent selected from a non-reactive atom, a non-reactive group, a hydroxyl group and an amino group, and at least two members selected from R1a, R2a, R3a and R4a are a hydroxyl group, a carboxyl group or an amino group; is subjected to an esterification reaction or an amidation reaction with a polymerizable unsaturated compound (e.g., an alcohol, a carboxylic acid, an amine) in the presence of a catalyst comprising an element selected from the Group 3 elements, such as a samarium compound, to obtain a polymerizable adamantane derivative having at least one polymerizable unsaturated group in high yield.

  以下化学式所示的化合物：其中R1a、R2a、R3a和R4a中的每一个代表从非反应性原子、非反应性基团、羟基和氨基中选择的取代基，且在R1a、R2a、R3a和R4a中至少有两个成员是羟基、羧基或氨基；在催化剂的存在下，与可聚合的不饱和化合物（例如醇、羧酸、胺）进行酯化反应或酰胺化反应，所述催化剂包括从第三族元素中选择的元素，如钐化合物，以高产率获得至少具有一个可聚合不饱和基团的可聚合性金刚烷衍生物。
• Fluorine-containing graft copolymer and adhesive and composite membrane made thereof
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP0183989A2

  公开（公告）日：1986-06-11

  A graft copolymer consisting essentially of a main chain polymer having a glass transition temperature (Tg) of at least 30°C and a graft chain fluorine-containing polymer having a repeating unit of the formula: wherein R1 is a hydrogen atom or a lower alkyl group, and R2 is a polyfluoroalkyl group.

  一种接枝共聚物，主要由玻璃化转变温度（Tg）至少为 30°C 的主链聚合物和具有以下重复单元的接枝链含氟聚合物组成： 其中 R1 为氢原子或低级烷基，R2 为多氟烷基。
• COATING COMPOSITION AND SURFACE-COATED MOLDING PRODUCED THEREWITH
  申请人：MITSUBISHI RAYON CO., LTD.

  公开号：EP0696621A1

  公开（公告）日：1996-02-14

  A coating composition comprising: (a) a cross-linking polymerizable compound (a-1) having at least two (meth)acryloyloxy groups in its molecule or a mixture of the compound (a-1) and a compound (a-2) copolymerizable therewith; (b) fine silica particles with their surfaces modified with a hydrolyzate of a mixture of a silane compound (b-1) capable of binding with the component (a) and another silane compound (b-2) incapable of binding with the component (a); and (c) an initiator for actinic radiation-induced polymerization. The composition can give a cured coating having a high surface strength and an excellent weathering resistance, and is applicable without using any solvent.

  一种涂料组合物，包括(a) 可交联聚合的化合物（a-1），其分子中至少有两个（甲基）丙烯酰氧基，或该 化合物（a-1）和可与之共聚的化合物（a-2）的混合物；(b) 细二氧化硅颗粒，其表面用能与组分（a）结合的硅烷化合物（b-1）和不能与组分 （a）结合的另一种硅烷化合物（b-2）的混合物的水解物改性；以及 (c) 用于光辐射诱导聚合的引发剂。该组合物可制成具有高表面强度和优异耐候性的固化涂层，且无需使用任何溶剂。
• (METH)ACRYLIC ESTER COPOLYMERS AND PROCESS FOR PRODUCING THE SAME
  申请人：NIPPON SODA CO., LTD.

  公开号：EP0942018A1

  公开（公告）日：1999-09-15

  Random or block copolymers of a (meth)acrylic ester, which comprise structural units represented by general formulae (I) and (II) and have a number-average molecular weight of 1,000 to 50,000, a weight-average molecular weight (Mw) to number-average molecular weight (Mn) ratio, M w/Mn, of 1.00 to 1.40, and a ratio of the repeating structural units represented by formula (I) to those represented by formula (II) of 1/9 to 9/1 (wherein R1 and R2 each independently represents hydrogen or methyl; R3 represents an optionally substituted C7-15 alicyclic group or an alkyl group having the alicyclic group; and R4 represents hydrogen, an optionally substituted C1-12 alkyl, optionally substituted C3-6 alicyclic or heterocyclic group, or substituted silyl group having a C1-8 alkyl and/or aryl group). The copolymers have each a unimodal narrow molecular weight distribution and an essential skeleton having at least one segment with a controlled structure comprising (meth)acrylic ester units each having an organic group containing a bulky alicyclic group.

  (甲基)丙烯酸酯的无规或嵌段共聚物，它包括通式(I)和(II)所代表的结构单元，其数均分子量为1,000至50,000，重均分子量(Mw)与数均分子量(Mn)之比M w/Mn为1.00至1.40，以及由式(I)表示的重复结构单元与由式(II)表示的重复结构单元之比为1/9至9/1（其中R1和R2各自独立地代表氢或甲基；R3代表任选取代的C7-15脂环基或具有脂环基的烷基；R4代表氢、任选取代的C1-12烷基、任选取代的C3-6脂环基或杂环基、或具有C1-8烷基和/或芳基的取代硅烷基）。共聚物具有单峰窄分子量分布，其基本骨架至少有一个具有受控结构的区段，该受控结构由(甲基)丙烯酸酯单元组成，每个单元都具有含有一个大脂环基团的有机基团。