2-(4-(bromomethyl)phenyl)-2-methyl-1,3-dioxolane | 111818-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-(bromomethyl)phenyl)-2-methyl-1,3-dioxolane
• 英文别名: 2-(4-bromomethylphenyl)-2-methyl-1,3-dioxolane；2-[4-(bromomethyl)phenyl]-2-methyl-1,3-dioxolane
• CAS: 111818-36-1
• 化学式: C₁₁H₁₃BrO₂
• 分子量: 257.127
• InChiKey: OWFSYXHZVMCHBU-UHFFFAOYSA-N

物化性质

• 沸点：
  317.2±37.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  2-(4-(bromomethyl)phenyl)-2-methyl-1,3-dioxolane 在 正丁基锂 、 (R,R)-(p-cymene)(OTf)(H2NCHPhCHPhNSO2(4-CH3C6H4)) 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 25.0 ℃ 、5.07 MPa 条件下， 反应 35.17h， 生成 (R)-1-(4-(2-(1,2,3,4-tetrahydroquinolin-2-yl)ethyl)phenyl)ethanone
  参考文献：
  名称：

  离子液体中钌催化的不对称氢化对映体高对映选择性地合成手性四氢喹啉和四氢异喹啉

  摘要：

  AbstractAsymmetric hydrogenation reactions of quinolines and 3,4‐dihydroisoquinolines using the chiral cationic ruthenium complex Ru(TsDPEN) [TsDPEN=N‐(p‐toluenesulfonyl)‐1,2‐diphenylethylenediamine] as catalyst in neat imidazolium ionic liquids have been investigated. The catalytic performance was influenced by the anion of the ionic liquids for both substrate classes. A range of 2‐alkyl‐substituted 1,2,3,4‐tetrahydroquinolines and 1‐alkyl‐substituted 1,2,3,4‐tetrahydroisoquinolines was obtained in high yields with up to >99% ee. Interestingly, the hydrogenation of quinoline derivatives bearing a carbonyl group was selective for the CN (quinoline) over the CO (ketone) bonds, while such a unique chemoselectivity was not observed in methanol. Furthermore, the ruthenium catalysts could be easily recycled at least 5 times in the asymmetric hydrogenation of 3,4‐dihydroisoquinoline by solvent extraction. To further facilitate the recovery of catalyst and reduce the use of organic solvent, a thin film of ionic liquid containing Ru(TsDPEN) was supported on silica gels. This supported ionic liquid‐phase catalyst was effective in the asymmetric hydrogenation of quinoline, and could be recycled at least 6 times by simple filtration.magnified image

  DOI：

  10.1002/adsc.201300698
• 作为产物：
  描述：

  对甲基苯乙酮 在 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 16.0h， 生成 2-(4-(bromomethyl)phenyl)-2-methyl-1,3-dioxolane
  参考文献：
  名称：

  离子液体中钌催化的不对称氢化对映体高对映选择性地合成手性四氢喹啉和四氢异喹啉

  摘要：

  AbstractAsymmetric hydrogenation reactions of quinolines and 3,4‐dihydroisoquinolines using the chiral cationic ruthenium complex Ru(TsDPEN) [TsDPEN=N‐(p‐toluenesulfonyl)‐1,2‐diphenylethylenediamine] as catalyst in neat imidazolium ionic liquids have been investigated. The catalytic performance was influenced by the anion of the ionic liquids for both substrate classes. A range of 2‐alkyl‐substituted 1,2,3,4‐tetrahydroquinolines and 1‐alkyl‐substituted 1,2,3,4‐tetrahydroisoquinolines was obtained in high yields with up to >99% ee. Interestingly, the hydrogenation of quinoline derivatives bearing a carbonyl group was selective for the CN (quinoline) over the CO (ketone) bonds, while such a unique chemoselectivity was not observed in methanol. Furthermore, the ruthenium catalysts could be easily recycled at least 5 times in the asymmetric hydrogenation of 3,4‐dihydroisoquinoline by solvent extraction. To further facilitate the recovery of catalyst and reduce the use of organic solvent, a thin film of ionic liquid containing Ru(TsDPEN) was supported on silica gels. This supported ionic liquid‐phase catalyst was effective in the asymmetric hydrogenation of quinoline, and could be recycled at least 6 times by simple filtration.magnified image

  DOI：

  10.1002/adsc.201300698

文献信息

• Pyrazole oxime derivatives and compositions
  申请人：Nihon Nohyaku Co., Ltd.

  公开号：US04843068A1

  公开（公告）日：1989-06-27

  A pyrazole oxime derivative represented by the general formula (I) which is useful as an insecticide and fungicide, ##STR1## wherein the structural elements are defined in the specification, and the method of controlling said pests. The compounds represented by the general formula (I) can be synthesized by the methods disclosed in the specification.

  一种由通式（I）表示的吡唑肟衍生物，可用作杀虫剂和杀菌剂，##STR1## 其中结构元素在规范中定义，并控制所述害虫的方法。通式（I）表示的化合物可以通过规范中披露的方法合成。
• Synthesis of 2<i>H</i> -Azirines by Iridium-Catalyzed Decarboxylative Ring Contraction of Isoxazol-5(4<i>H</i> )-ones
  作者：Kazuhiro Okamoto、Takuya Shimbayashi、Masato Yoshida、Atsushi Nanya、Kouichi Ohe

  DOI：10.1002/anie.201602241

  日期：2016.6.13

  A phosphine‐free iridium‐catalyzed reaction of isoxazol‐5(4H)‐ones (isoxazolones) has been developed, and affords 2H‐azirines through decarboxylation and ring contraction. This method provides an efficient and environmentally benign protocol which could replace the conventional approaches used to synthesize 2H‐azirines.

  现已开发出无膦的铱催化的异恶唑5（4 H）-酮（异恶唑酮）反应，并通过脱羧和环收缩反应生成2 H-叠氮基。该方法提供了一种高效且对环境无害的方案，可以代替用于合成2 H嗪的常规方法。
• Preparation of multifunctional supported metallocene catalyst using organic multifunctional modifier for synthesizing polyethylene/clay nanocomposites via in situ intercalative polymerization
  作者：Changyi Ren、Xiaohua Du、Li Ma、Yanhui Wang、Jun Zheng、Tao Tang

  DOI：10.1016/j.polymer.2010.05.041

  日期：2010.7

  A new type of multifunctional ammonium modifier with carbonyl group and vinyl group was synthesized to prepare multifunctional montmorillonites (F-MMTs), which were used as multifunctional catalyst supports for in situ ethylene polymerization. High loading of metallocene catalyst in the galleries of F-MMT had been achieved due to the presence of carbonyl group in the multifunctional modifier. XRD profiles and TEM images showed that polyethylene/montmorillonite (PE/F-MMT) nanocomposites with exfoliated structure could be synthesized using the intercalated catalyst described above, even when the content of MMT was very high (more than 15.1 wt%). The as-produced PE/F-MMTs nanocomposites were composed of flower-like particles with a diameter of about 5 pm. A thermal stable monoclinic phase was observed in PE/F-MMT nanocomposites. Comparatively, the resultant PE/F-MMT nanocomposites showed low gas permeability. Interfacial interaction between PE matrix and F-MMT was enhanced due to the chemical linking between the two components via copolymerization of ethylene with vinyl group of F-MMT. Thus the resultant PE/F-MMT nanocomposites showed good structural stability. (C) 2010 Elsevier Ltd. All rights reserved.
• A pyrazole oxime derivative and its production and use
  申请人：NIHON NOHYAKU CO., LTD.

  公开号：EP0234045B1

  公开（公告）日：1992-09-02
• US4843068A
  申请人：——

  公开号：US4843068A

  公开（公告）日：1989-06-27