3-bromo-2-(bromomethyl)-2-methylpropyl acetate | 181134-65-6

• 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-bromo-2-(bromomethyl)-2-methylpropyl acetate
• 英文别名: 3-bromo-2-bromomethyl-2-methylpropyl acetate；[3-bromo-2-(bromomethyl)-2-methylpropyl] acetate
• CAS: 181134-65-6
• 化学式: C₇H₁₂Br₂O₂
• 分子量: 287.979
• InChiKey: ONESRDYPJJTXBK-UHFFFAOYSA-N

物化性质

• 沸点：
  284.7±30.0 °C(Predicted)
• 密度：
  1.655±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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-bromo-2-(bromomethyl)-2-methylpropyl acetate 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以43.9%的产率得到3-溴甲基-3-甲基-1-氧杂环丁烷
  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
• 作为产物：
  描述：

  1,1,1-三(羟甲基)乙烷 、 溶剂黄146 在 硫酸 、 sodium bromide 作用下， 反应 168.0h， 以95%的产率得到3-bromo-2-(bromomethyl)-2-methylpropyl acetate
  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

• Synthesis and copolymerization of azidomethyl-substituted oxetanes: the morphology of statistical block copolymers
  作者：Timur I. Mukhametshin、Aleksei I. Petrov、Nina V. Kuznetsova、Vladimir A. Petrov、Natalia V. Averianova、Ilgiz Kh. Garaev、Anatoly V. Kostochko、Aidar T. Gubaidullin、Dmitry B. Vinogradov、Pavel V. Bulatov

  DOI：10.1007/s10593-017-2128-3

  日期：2017.6

  3,3-Bis(azidomethyl)oxetane and 3-azidomethyl-3-methyloxetane were obtained by bromination of pentaerythritol and metriol with a mixture of hydrobromic, acetic, and sulfuric acids, followed by cyclization in the presence of a phase-transfer catalyst TBAB, with the formation of oxetane ring and replacement of bromide substituents with azide ions. The copolymerization reaction of 3,3-bis-(azidomethyl)oxetane

  3,3-双（叠氮基甲基）氧杂环丁烷和3-叠氮基甲基-3-甲基氧杂环丁烷是通过季戊四醇和间苯二酚与氢溴酸，乙酸和硫酸的混合物溴化，然后在相转移催化剂TBAB的存在下环化而获得的，形成氧杂环丁烷环并用叠氮化物离子取代溴化物取代基。3，3-双-（叠氮甲基）氧杂环丁烷和3-叠氮甲基-3-甲基氧杂环丁烷的共聚反应在由三异丁基铝和水制备的催化体系的存在下进行。使用小角度和广角X射线衍射分析方法确定合成共聚物的无定形晶体和畴结构。我们还提供了有关这些统计共聚物中构象和弛豫转变的数据。
• Fluorinated thermoset polyurethane elastomers prepared from polyether prepolymers formed mono-substituted fluorinated oxetane monomers
  申请人：——

  公开号：US20040087759A1

  公开（公告）日：2004-05-06

  This application is directed to novel fluorinated polymers and prepolymers derived from mono-substituted oxetane monomers having fluorinated alkoxymethylene side-chains and the method of making these compositions. The mono-substituted fluorinated oxetane monomers having fluorinated alkoxymethylene side-chains are prepared in high yield by the reaction of a fluorinated alkoxides with either 3-halomethyl-3-methyloxetane premonomers or aryl sulfonate derivative of 3-hydroxymethyl-3-methyloxetane premonomers. Preparation of a mono-substituted 3-bromomethyl-3-methyloxetane premonomer via a simple, high yield process amenable to commercial scaleup is also disclosed. The fluorinated oxetane monomers of this invention can be readily homo/co-polymerized in the presence of a Lewis acid and polyhydroxy compounds to obtain hydroxy-terminated polyether prepolymers having fluorinated alkoxymethylene side chains. Additionally, the fluorinated oxetane monomers can be copolymerized with non-fluorinated monomers such as tetrahydrofuran to give polyether prepolymers with improved hydrocarbon compatibility. These prepolymers are polydisperse and exhibit number average molecular weights from 5,000 to about 50,000. These prepolymers are amorphous oils with primary hydroxy end-groups and thus function efficiently as the soft block for the synthesis of a variety of thermoset/thermoplastic elastomers and plastics having the characteristics of very low surface energy, high hydrophobicity, low glasss transition temperature and low coefficient of friction. The polyurethanes derived from the prepolymers of this invention are elastomeric and, in addition to the above characteristics, exhibit high moisture resistance, high tear strength and excellent adhesion to a variety of substrates.

  该申请涉及一种新型的含氟聚合物和预聚物，其源自于具有含氟烷氧甲基侧链的单取代氧杂环戊烷单体，并且涉及制备这些组合物的方法。这些具有含氟烷氧甲基侧链的单取代氟氧杂环戊烷单体可通过将含氟烷氧化物与3-卤代甲基-3-甲氧基氧杂环戊烷预聚物或3-羟甲基-3-甲氧基氧杂环戊烷预聚物的芳基磺酸衍生物反应而高产率制备。此外，还公开了一种简单、高产率的方法，通过该方法可以制备单取代3-溴甲基-3-甲氧基氧杂环戊烷预聚物，该方法适用于商业规模生产。本发明的含氟氧杂环戊烷单体可以在路易斯酸和多羟化合物的存在下容易地进行同聚/共聚反应，以获得具有含氟烷氧甲基侧链的羟基终止的聚醚预聚物。此外，含氟氧杂环戊烷单体可以与四氢呋喃等非含氟单体共聚，以获得具有改善烃类相容性的聚醚预聚物。这些预聚物是多分散的，并且具有5,000至约50,000的数平均分子量。这些预聚物是无定形油状物，具有主要的羟基末端，因此可以有效地作为合成各种热固性/热塑性弹性体和塑料的软块，具有极低的表面能、高疏水性、低玻璃转移温度和低摩擦系数的特性。本发明的预聚物衍生的聚氨酯具有弹性，并且除了上述特性外，还具有高湿度抗性、高撕裂强度和对各种基材的优异粘附性。
• MONO-SUBSTITUTED FLUORINATED OXETANE MONOMERS
  申请人：AEROJET-GENERAL CORPORATION

  公开号：EP0811004B1

  公开（公告）日：2006-12-06
• EP0811004A4
  申请人：——

  公开号：EP0811004A4

  公开（公告）日：1998-09-30
• US5650483A
  申请人：——

  公开号：US5650483A

  公开（公告）日：1997-07-22