3-[(2,2,3,3,3-pentafluoropropoxy)methyl]-3-methyloxetane | 449177-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环丁烷
• 英文名称: 3-[(2,2,3,3,3-pentafluoropropoxy)methyl]-3-methyloxetane
• 英文别名: 3-methyl-3-(2,2,3,3,3-pentafluoropropyloxymethyl)oxetane；3-(1H,1H-perfluoropropan-1-oxymethyl)-3-methyloxetane；Oxetane, 3-methyl-3-((2,2,3,3,3-pentafluoropropoxy)methyl)-；3-methyl-3-(2,2,3,3,3-pentafluoropropoxymethyl)oxetane
• CAS: 449177-94-0
• 化学式: C₈H₁₁F₅O₂
• 分子量: 234.166
• InChiKey: WTXTVOBDAYMETL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,1,1-三(羟甲基)乙烷 在 硫酸 、 四丁基溴化铵 、 sodium bromide 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 216.0h， 生成 3-[(2,2,3,3,3-pentafluoropropoxy)methyl]-3-methyloxetane
  参考文献：
  名称：

  Synthesis and characterization of environmentally benign, semifluorinated polymers and their applications in drug delivery

  摘要：

  We describe the synthesis, physicochemical studies and pharmaceutical assessment of a class of pegylated semifluorinated amphiphilic block-copolymers based on short pendant fluorinated side chains attached to moderately hydrophobic units. These polymers allowed us to investigate how the balance between hydrophobicity and fluorophilicity in the polymer can be tuned to match that of small molecules to be used in drug delivery. Remarkably, we found that using short perfluoroethyl groups in the polymer allows the preferential stabilization of nanoemulsions based on isoflurane, a fluorinated anesthetic made partly hydrophobic by the presence of a chlorine atom. In comparison, nanoemulsions of sevoflurane, a purely fluorophilic anesthetic, were not as stable. The lipophilicity of the polymers was also investigated in regards to solvation of hydrophobic molecules. Surface properties such as critical micelle concentration (CMC) and surface tension demonstrated the uniqueness of these fluorinated amphiphiles. Finally, the use of short perfluoroethyl chains makes these polymers environmentally benign in terms of bioaccumulation and toxicity. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2016.09.001

文献信息

• A Ruthenium-Catalyzed Hydrosilane-Induced Polymerization of 3-Alkyl-3-hydroxymethyloxetane Derivatives: Facile Access to Functionalized Polyoxetanes by Virtue of Organosilyl Groups
  作者：Nari-aki Harada、Jushiro Yasuhara、Yukihiro Motoyama、Osamu Fujimura、Tetsuro Tsuji、Takeshi Takahashi、Yoshiaki Takahashi、Hideo Nagashima

  DOI：10.1246/bcsj.20100155

  日期：2011.1.15

  Ring-opening polymerization of 3-alkyl-3-alkoxymethyl- or 3-alkyl-3-siloxymethyloxetanes is catalyzed by a triruthenium cluster, [Ru3μ3-(η2,η3,η5-C12H8)}(CO)7], in the presence of trialkylsilanes, providing a novel accessible method for functionalized polyoxetanes of Mn = 103–105. Oxetanes having alkoxy-, fluoroalkoxy-, triethyleneglycoloxy-, and trialkylsiloxy functions undergo polymerization and copolymerization. Consumption rates of two monomers in the copolymerization of 3-benzyloxymethyl- and 3-trimethylsiloxymethyl-3-alkyloxetanes are almost the same, indicating formation of random copolymers. The organosilyl group in the polymer and copolymers with siloxymethyl side chains is converted to CH2OH or CH2OCOR groups by hydrolysis or silyl/acyl exchange. These protocols give the way to access polymers or copolymers bearing OH and OCOR side chains. A ruthenium-catalyzed reaction of 3-ethyl-3-hydroxymethyloxetane with trialkylsilanes results in dehydrogenative silylation to give 3-ethyl-3-siloxymethyloxetane, which is followed by ring-opening polymerization. Combination of tandem dehydrogenative silylation/ring-opening polymerization/the silyl/acyl exchange realizes one-pot synthesis of polymers with CH2OCOR side chains from 3-ethyl-3-hydroxymethyloxetane. DSC analyses of the formed polymers provided Tg and Tm data, which are a good example showing that the polymer properties are controlled by appropriate selection of functional groups at the side chain.

  三价铑簇[Ru3μ3-(η2,η3,η5-C12H8)}(CO)7]可以在三烷基硅烷的存在下催化3-烷基-3-烷氧甲基或3-烷基-3-硅氧甲基环状醚的环开聚合反应，提供了一种新型的制备功能化聚醚(Mn=103–105)的方法。3-烷氧基、3-氟烷氧基、3-三乙二醇氧基和3-三烷基硅氧基醚基环醚可以进行聚合和共聚反应。消耗速率:在3-苄氧甲基和3-三甲基硅氧甲基-3-烷氧基环醚共聚反应中两种单体的消耗速率几乎相同，表明形成了无规共聚物。在具有硅氧甲基侧链的聚合物和共聚物中的有机硅基团可以被转换成CH2OH或CH2OCOR基团，通过水解或硅/酰交换反应。这些反应方法提供了一种合成带OH或OCOR侧链的聚合物或共聚物的方法。由铑催化的3-乙基-3-羟甲基环醚与三烷基硅烷的反应得到3-乙基-3-硅氧甲基环醚，再进行环开聚合反应。通过脱氢硅烷化/环开聚合/硅/酰交换的串联反应，可以实现从3-乙基-3-羟甲基环醚的一锅法合成带CH2OCOR侧链的聚合物。通过DSC分析得到的玻璃化转变温度和熔点数据说明只要合理地选择好侧链上的功能基团，就可以精确地控制聚合物材料的其他性质。
• Functional polymers via surface modifying agents, and methods for polymeric surface modification
  申请人：Wynne Joseph Kenneth

  公开号：US20060154083A1

  公开（公告）日：2006-07-13

  Polymers, and particularly conventional commodity bulk polymers, are modified to have a surface activity of interest using a surface modifying polymer that includes a moiety that favors migration to the surface of the bulk polymer together with a moiety provides the activity of interest (e.g., biocidal, wettability modifying (hydrophobic or hydrophilic), resistance to radiant energy, providing a functional group for functionalizing the surface, etc.). The surface modifying polymer is combined with the bulk polymer, and, due to the presence of the moiety that favors migration, concentrates primarily on the surface of the bulk polymer such that the moiety that provides the activity of interest is located primarily on the surface of the bulk polymeric article which is produced. Advantageously, only a minimal amount (such as, e.g., about 2 weight %) of polymeric surface modifier is needed. Being able to achieve desired properties (such as biocidal activity, wettability modification, etc.) without needing much polymeric surface modifier is highly advantageous.

  聚合物，特别是传统的大宗商品聚合物，通过使用表面改性聚合物进行修改，使其具有感兴趣的表面活性。表面改性聚合物包括一个偏爱迁移到大宗聚合物表面的基团以及提供感兴趣活性的基团（例如，生物杀灭作用，润湿性改性（疏水或亲水），对辐射能的抵抗力，提供功能基团以进行表面功能化等）。表面改性聚合物与大宗聚合物结合，由于存在偏爱迁移的基团，主要集中于大宗聚合物表面，从而使提供感兴趣活性的基团主要位于所制备的大宗聚合物制品的表面。优点是只需要最少量的聚合物表面改性剂（例如约2重量％）。能够在不需要太多聚合物表面改性剂的情况下实现所需的性质（例如生物杀灭活性，润湿性改性等）非常有优势。
• METHOD FOR TREATING A LITHOGRAPHIC PRINTING PLATE
  申请人：Maessen Peter

  公开号：US20100137180A1

  公开（公告）日：2010-06-03

  A method for treating a lithographic printing plate including the step of applying a liquid containing a surfactant to the plate, characterized in that the surfactant includes at least one hydrophilic segment including polyglycerol, and at least one hydrophobic segment selected from an optionally substituted alkylene group, an alkyl or aryl substituted poly(meth)acrylate, an optionally substituted polyester, polyether, polyurethane, polycarbosilane, polysiloxane, polystyrene and/or a polymer including a perfluoroalkyl group with the proviso that the liquid is not applied as a fountain solution.
• US7771793B2
  申请人：——

  公开号：US7771793B2

  公开（公告）日：2010-08-10
• US7842388B2
  申请人：——

  公开号：US7842388B2

  公开（公告）日：2010-11-30