o-bromomethylacetophenone | 168551-52-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: o-bromomethylacetophenone
• 英文别名: 1-[2-(bromomethyl)phenyl]ethanone
• CAS: 168551-52-8
• 化学式: C₉H₉BrO
• 分子量: 213.074
• InChiKey: XBSHRGYQEKZCHB-UHFFFAOYSA-N

物化性质

• 沸点：
  282.9±23.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  o-bromomethylacetophenone 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 水 、 甲苯 为溶剂， 反应 26.0h， 生成 1-(2-(2-(quinolin-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：

  1-甲基苯基乙酮 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 生成 o-bromomethylacetophenone
  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

• AZACYCLYLISOQUINOLINONE AND ISOINDOLINONE DERIVATIVES AS HISTAMINE-3 ANTAGONISTS
  申请人：Zhou Dahui

  公开号：US20090069370A1

  公开（公告）日：2009-03-12

  The present invention provides a compound of formula I and the use thereof for the treatment of a central nervous system disorder related to or affected by the histamine-3 receptor.

  本发明提供了一种公式I的化合物，以及该化合物用于治疗与组胺-3受体相关或受其影响的中枢神经系统疾病。
• 一种光电材料中间体2-氯-4-苯基苯并[h]喹 唑啉的合成方法
  申请人：西安欧得光电材料有限公司

  公开号：CN108033918B

  公开（公告）日：2020-12-25

  本发明公开了一种光电材料中间体2‑氯‑4‑苯基苯并[h]喹唑啉的合成方法，反应物A与苯甲醛、尿素经过合环反应、氯代反应、氧化反应、wittig反应、环化反应生成式1化合物2‑氯‑4‑苯基苯并[h]喹唑啉，所述反应物A为式2化合物或式3化合物。本发明公开的2‑氯‑4‑苯基苯并[h]喹唑啉的合成方法可以进行大批量生产，提高了实验操作过程中的安全性与可操作性，降低了剧毒废液后处理的成本，所用的化学品均简单易得、相对廉价，并且提高了2‑氯‑4‑苯基苯并[h]喹唑啉的合成总收率。
• ISOINDOLE-IMIDE COMPOUNDS, COMPOSITIONS, AND USES THEREOF
  申请人：Robarge Michael J.

  公开号：US20090286986A1

  公开（公告）日：2009-11-19

  The invention relates to isoindole-imide compounds and pharmaceutically acceptable salts, hydrates, solvates, clathrates, enantiomers, diastereomers, racemates, or mixtures of stereoisomers thereof, pharmaceutical compositions comprising these isoindole-imide compounds, and methods for reducing the level of cytokines and their precursors in mammals. In particular, the invention pertains to isoindole-imide compounds that are potent inhibitors of the production of TNF-α in mammals. The isoindole-imides described herein are useful for treating or preventing diseases or disorders in mammals, for example, cancers, such as solid tumors and blood-born tumors; heart disease, such as congestive heart failure; osteoporosis; and genetic, inflammatory; allergic; and autoimmune diseases.

  本发明涉及isoindole-imide化合物及其药学上可接受的盐、水合物、溶剂物、笼合物、对映体、非对映异构体、外消旋体或其立体异构体混合物，以及包括这些isoindole-imide化合物的制药组合物，以及在哺乳动物中降低细胞因子及其前体水平的方法。具体而言，本发明涉及对哺乳动物中TNF-α产生的强效抑制剂isoindole-imide化合物。本文所述的isoindole-imides用于治疗或预防哺乳动物中的疾病或疾病，例如，癌症，如实体肿瘤和血液肿瘤；心脏病，如充血性心力衰竭；骨质疏松症；以及遗传性、炎症性、过敏性和自身免疫性疾病。
• ISOINDOLINE PDE10 INHIBITORS
  申请人：Bunda Jamie L.

  公开号：US20130203756A1

  公开（公告）日：2013-08-08

  The present invention is directed to isoindolinone compounds which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 10 (PDE10). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

  本发明涉及isoindolinone化合物，其可用作治疗与磷酸二酯酶10（PDE10）相关的中枢神经系统疾病的治疗剂。本发明还涉及使用这些化合物治疗神经系统和精神疾病，如精神分裂症、精神病或亨廷顿病，以及与纹状体功能减退或基底节功能障碍有关的疾病。
• Siloxane polyphotoinitiators of the substituted acetophenone type
  申请人：LOCTITE CORPORATION

  公开号：EP0162572A1

  公开（公告）日：1985-11-27

  An organopolysiioxane photoinitiator having an average of at least two siloxane units, of which at least an average of one siloxane unit per organopolysiloxane molecule has the formula: wherein a is an integer of 1-3, b is an integer of 0-2 and a plus b equals 1-3; R is C1-C10 hydrocarbyl or halogen substituted C1-C10 hydrocarbyl; and X is a substituted acetophenone photomoiety selected from: where R1 is any substituent which will not interfere with hydrosilation, n is an integer between 0 and 5 in formulas (II), (Ila), (III), (IIIa), (IV) and (IVa) and between 0 and 4 in formula (III) and (IIIa); m is 0 or 1; R2 is alkyl or substituted alkyl; R3 is H, alkyl or aryl; R4 is a divalent hydrocarbon group having between 2 and 10 carbon atoms or an alkylene oxy alkylene group; R5 is a group selected from H, alkyl, aryl, organosilyl, or the reaction product of an isocyanate esterification reagent or an etherification reagent with the hydroxyl product formed when R5 is H and R6 is a trivalent hydrocarbon or hydrocarbon oxyhydrocarbon group. The silicones are prepared by hydrosilation of the corresponding olefinically or acetylenically unsaturated acetophenones.

  一种平均具有至少两个硅氧烷单元的有机聚硅氧烷光引发剂，其中每个有机聚硅氧烷分子平均具有至少一个硅氧烷单元，其化学式为 其中 a 是 1-3 的整数，b 是 0-2 的整数，a 加 b 等于 1-3；R 是 C1-C10 碳氢基或卤素取代的 C1-C10 碳氢基；X 是选自以下各项的取代苯乙酮光异构体： 其中 R1 是不会干扰水合作用的任何取代基，n 在式(II)、(Ila)、(III)、(IIIa)、(IV)和(IVa)中是 0 至 5 之间的整数，在式(III)和(IIIa)中是 0 至 4 之间的整数；m 是 0 或 1；R2 是烷基或取代的烷基；R3 是 H、烷基或芳基；R4 是具有 2 至 10 个碳原子的二价烃基或烷氧基烷基； R5 是选自 H、烷基、芳基、有机硅基的基团，或异氰酸酯酯化试剂或醚化试剂与 R5 为 H 时形成的羟基产物的反应产物，R6 是三价烃基或烃氧基烃基。 硅酮是通过相应的烯烃或乙炔不饱和苯乙酮的加氢反应制备的。