3-{[(6-bromohexyl)oxy]methyl}-3-methyloxetane | 103781-35-7

• 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-{[(6-bromohexyl)oxy]methyl}-3-methyloxetane
• 英文别名: 3-((6-bromohexyloxy)methyl)-3-methyloxetane；3-(6-bromohexyloxymethyl)-3-methyloxetane；3-(8-bromo-2-oxaoctyl)-3-methyloxetane；3-[(6-bromohexyloxy)methyl]-3-methyloxetane；3-(6-bromohexoxymethyl)-3-methyloxetane
• CAS: 103781-35-7
• 化学式: C₁₁H₂₁BrO₂
• 分子量: 265.191
• InChiKey: IPMVZJJKTCBGMM-UHFFFAOYSA-N

物化性质

• 沸点：
  297.4±15.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  8
• 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：
  2

反应信息

• 作为反应物：
  描述：

  3-{[(6-bromohexyl)oxy]methyl}-3-methyloxetane 在 4-二甲氨基吡啶 、 sodium hydroxide 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 potassium iodide 作用下， 以 乙醇 、 二氯甲烷 、 丁酮 为溶剂， 反应 73.0h， 生成 (R)-(-)-4-(1-methylheptyloxycarbonyl)-3-fluorophenyl 4'-[6-(3-methyloxetan-3-ylmethoxy)hexyloxy]biphenyl-4-carboxylate
  参考文献：
  名称：

  Side­chain liquid crystal polymers derived from oxetane monomers containing 2­ or 3­fluorophenyl moieties in the core of the mesogen

  摘要：

  通过阳离子开环反应制备了两类侧链液晶聚合物，这些聚合物由取代的氧杂环烷烃构成。每个末端附加的侧链聚合物都有一个由六个亚甲基单元组成的柔性间隔器，将液晶芳香核与聚合物主链分隔开。核心单元设计为包含一个2-氟或3-氟苯基单元，并具有(R)-(−)-1-甲基庚基、(S)-(+)-2-甲基丁基或1-丙基丁基的末端链。本研究中产生的材料与之前报道的未取代母体材料进行了比较，以评估核心中侧向氟取代基的影响。大多数单体表现出低熔点，呈现出层状相C/C*和层状相A/A*。发现3-氟苯基单体的行为与其未氟化的母体相似，而2-氟的类似物显示出显著较低的相变温度。所有聚合物在较宽的温度范围内表现出层状相C/C*和层状相A/A*，且具有相对较低的玻璃化转变温度（Tg）。一些聚合物展现出异常大的层状相C/C*的温度范围，例如从0.8°C到190°C。

  DOI：

  10.1039/b009426i
• 作为产物：
  描述：

  3-甲基-3-羟甲基氧杂环丁烷 、 1,6-二溴己烷 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 hexanes 、 水 为溶剂， 反应 26.5h， 以53%的产率得到3-{[(6-bromohexyl)oxy]methyl}-3-methyloxetane
  参考文献：
  名称：

  [EN] TRANSITION-METAL CHARGE-TRANSPORT MATERIALS, METHODS OF FABRICATION THEREOF, AND METHODS OF USE THEREOF
  [FR] MATERIAUX DE TRANSPORT DE CHARGE DE METAUX DE TRANSITION, LEURS PROCEDES DE FABRICATION ET D'UTILISATION

  摘要：

  公开号：

  WO2005123754A3

文献信息

• A Facile Synthesis of Oxetane Derivatives for Preparing Cross-Linked Polyoxetane Resins Bearing the Bromide at the Spacer End
  作者：Masatoshi Motoi、Hiroshi Suda、Katsuhiko Shimamura、Shinsuke Nagahara、Mitsuru Takei、Shigeyoshi Kanoh

  DOI：10.1246/bcsj.61.1653

  日期：1988.5

  3-(6-Bromo-2-oxahexyl and 8-bromo-2-oxaoctyl)-3-methyloxetanes, and 1,8- and 1,10-bis(3-methyl-3-oxetanyl)-2,7-dioxaoctane and -2,9-dioxadecane were readily prepared in fairly good yields by the reaction of 3-hydroxymethyl-3-methyloxetane (1) with tetra- and hexamethylene dibromides in the presence of a phase-transfer catalyst. The formation of the mono- and disubstituted products depends upon the molar ratios of the dibromide to 1. The optimum reaction conditions for the etherification of 1 with tetramethylene dibromide were searched. The (ω-bromo-2-oxaalkyl)oxetanes were polymerized to give soluble polyoxetanes (\barMn 3500–5500) by cationic ring-opening polymerization. The use of the bisoxetanes, a new cross-linking agent, as a comonomer gave insoluble elastic polyoxetane resins having a pendant bromide at the spacer end.

  3-(6-溴-2-氧杂己基和8-溴-2-氧杂辛基)-3-甲基氧杂环丁烷，以及1,8-和1,10-双(3-甲基-3-氧杂环丁基)-2,7-二氧杂辛烷和-2,9-二氧杂癸烷，通过3-羟甲基-3-甲基氧杂环丁烷（1）与四亚甲基和六亚甲基二溴化物在相转移催化剂存在下的反应，以相当不错的产率方便地制备得到。单取代和双取代产物的形成取决于二溴化物与1的摩尔比。探索了1与四亚甲基二溴化物醚化反应的最佳条件。（ω-溴-2-氧杂烷基）氧杂环丁烷通过阳离子开环聚合反应聚合，得到可溶性聚氧杂环丁烷（平均分子量3500-5500）。作为新的交联剂，双氧杂环丁烷作为共聚单体使用，产生了具有间隔末端悬挂溴的不溶性弹性聚氧杂环丁烷树脂。
• Oxetane Derivatives and Their Polymers for Designing Functional Polymers Containing a Soft, Somewhat Polar Polyether Network as a Polymer Support
  作者：Masatoshi Motoi、Shinsuke Nagahara、Mitsuru Yokoyama、Eiichi Saito、Osamu Nishimura、Shigeyoshi Kanoh、Hiroshi Suda

  DOI：10.1246/bcsj.62.1572

  日期：1989.5

  Several oxetane derivatives having functional groups, such as ester, ketone, ether, acetal, and azo, at the end of 2-oxapolymethylene spacers which were linked to the C-3 carbon of an oxetane ring were readily prepared by a substitution reaction of the corresponding bromide of the oxetane. These oxetanes were polymerized by cationic ring-opening polymerization to give their polymers with molecular

  在与氧杂环丁烷环的 C-3 碳相连的 2-氧杂多亚甲基间隔基末端具有酯、酮、醚、乙缩醛和偶氮等官能团的几种氧杂环丁烷衍生物很容易通过以下取代反应制备：氧杂环丁烷的相应溴化物。这些氧杂环丁烷通过阳离子开环聚合反应得到分子量为 16000 至 1000 的聚合物，具体取决于所用单体的官能团结构。当在上述聚合中使用双氧杂环丁烷作为交联剂时，获得了含有柔软的、有些极性的聚醚网络作为聚合物载体的不溶性树脂。还研究了氧杂环丁烷衍生物及其聚合物的侧基官能团的一些化学反应。
• Nanostructured donor/acceptor interfaces in photovoltaic cells using columnar-grain films of a cross-linked poly(fluorene-alt-bithiophene)
  作者：Joana Farinhas、Quirina Ferreira、Roberto E. Di Paolo、Luís Alcácer、Jorge Morgado、Ana Charas

  DOI：10.1039/c1jm10195a

  日期：——

  We report on the fabrication of photovoltaic cells, PVs, with controlled donor/acceptor interfaces using a process based on the phase separation between a cross-linkable polyfluorene and polystyrene. Robust, nanostructured columnar-grain layers of a conjugated cross-linked polymer, F8T2Ox1 (an oxetane-functionalized derivative of poly(9,9-dioctylfluorene-alt-bithiophene)) are obtained after removal of polystyrene. These layers are used, in combination with 1-(3-methoxycarbonyl)propyl-1-phenyl-(6,6)C61 (PCBM) deposited by spin coating, to define donor/acceptor interfaces, as PVs' active layers. The performance of these cells is dependent on the dimensions of the surface structures. In particular, a significant power conversion efficiency improvement is observed upon decrease of column diameter, reflecting an improvement of the exciton dissociation. We find, however, that these efficiencies still fall below those of the PVs based on blends of the same components, but are larger than the ones found for planar bilayer PVs. Furthermore, PVs based on blends of cross-linked F8T2Ox1 and PCBM showed enhanced efficiency and thermal stability with respect to PVs based on blends of PCBM and the non-cross-linkable analogue poly(9,9-dioctylfluorene-alt-bithiophene). Taking into account that the columnar-grain morphology is recognised as the “ideal” architecture for PVs' active layer provided the column radii are of the order of few nanometres, this work gives a new insight into how to achieve efficient organic photovoltaic cells through the use of cross-linkable conjugated polymers as the electron-donor component.

  我们报告了一种基于交联聚氟烯和聚苯乙烯之间相分离的工艺，制造出具有可控供体/受体界面的光伏电池(PV)。去除聚苯乙烯后，获得了强韧的纳米结构柱状晶粒层，这是一种交联共轭聚合物F8T2Ox1（聚（9,9-二辛基氟烯-与-二噁烯）的一个氧杂环功能化衍生物）。这些层与通过旋涂沉积的1-(3-甲氧基碳酰基)丙基-1-苯基-(6,6)C61 (PCBM)结合，用于定义作为PV活性层的供体/受体界面。这些电池的性能依赖于表面结构的尺寸。特别地，随着柱直径的减小，观察到显著的功率转换效率提高，这反映了激子解离的改善。然而，我们发现这些效率仍低于基于相同组分混合物的PV，但高于平面双层PV的效率。此外，基于交联F8T2Ox1和PCBM混合物的PV在效率和热稳定性方面相较于基于PCBM和不可交联的类似物聚（9,9-二辛基氟烯-与-二噁烯）混合物的PV显示出增强的性能。考虑到柱状晶粒形态被认为是PV活性层的“理想”架构，只要柱半径在几个纳米的量级，本研究为如何通过使用可交联的共轭聚合物作为电子供体组件来实现高效有机光伏电池提供了新视角。
• Side Chain Liquid Crystalline Polyoxetanes with a Spacer-Separated Azobenzene Moiety. I. Preparation and Characterization
  作者：Masatoshi Motoi、Kunimasa Noguchi、Akio Arano、Shigeyoshi Kanoh、Akihiko Ueyama

  DOI：10.1246/bcsj.66.1778

  日期：1993.6

  Several oxetane derivatives carrying the azobenzene moiety at the C-3 position of the oxetane ring through the spacer arms of differing lengths were prepared by a substitution reaction of the corresponding bromide or p-toluenesulfonate residue of the oxetane with 4-hydroxyazobenzenes. The polymers of these oxetane derivatives were readily obtained by cationic ring-opening polymerization using the adequately increased amount of a THF· BF3 complex as an initiator at 20—30 °C. The liquid crystalline property of the polymers thus obtained were examined by differential scanning calorimetry and by optical polarized microscopy. From these measurements the influences of the p′-substituted azobenzene and of the spacer arm on the liquid crystalline property were found.

  通过氧杂环丁烷的相应溴化物或对甲苯磺酸残基与 4-羟基偶氮苯的取代反应，制备了几种在氧杂环丁烷环的 C-3 位通过不同长度的间隔臂携带偶氮苯分子的氧杂环丁烷衍生物。这些氧杂环丁烷衍生物的聚合物很容易通过阳离子开环聚合反应获得，该聚合反应使用了适当增加量的 THF- BF3 复合物作为引发剂，温度为 20-30 °C。通过差示扫描量热法和光学偏光显微镜对由此获得的聚合物的液晶特性进行了检测。通过这些测量，发现了 p′-取代偶氮苯和间隔臂对液晶特性的影响。
• Polymerizable liquid crystal composition and polymer thereof
  申请人：Ito Maiko

  公开号：US20060278851A1

  公开（公告）日：2006-12-14

  A polymerizable liquid crystal composition containing compounds represented by the formula (1-1) and the formula (1-2), compounds represented by the formula (2-1) and the formula (2-2), and a compound represented by the formula (3-1): the polymerizable liquid crystal composition having homogeneous, homeotropic, or hybrid alignment, which can be coated on a support substrate, for example, of a transparent plastic film such as a triacetyl cellulose film or cycloolefin polymer film, or glass, and is aligned on a substrate as a polymer film while maintaining the alignment.

  一种聚合液晶组合物，包含由公式（1-1）和公式（1-2）表示的化合物，由公式（2-1）和公式（2-2）表示的化合物，以及由公式（3-1）表示的化合物：该聚合液晶组合物具有均匀、家向或混合取向，可以涂覆在支撑基底上，例如透明塑料薄膜，如三乙酰纤维素薄膜或环氧烷基聚合物薄膜或玻璃上，并在保持取向的同时在基底上成膜。