2-[2-(2-溴-5-甲氧基苯基)乙基]环己酮 | 455330-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-[2-(2-溴-5-甲氧基苯基)乙基]环己酮
• 英文名称: 2-[2-(2-bromo-5-methoxyphenyl)ethyl]cyclohexanone
• 英文别名: (2-bromo-5-methoxyphenethyl)cyclohexan-1-one；2-(2-bromo-5-methoxy-phenethyl)-cyclohexanone；2-(2-Brom-5-methoxy-phenaethyl)-cyclohexanon；2-[2-(2-Bromo-5-methoxyphenyl)ethyl]cyclohexan-1-one
• CAS: 455330-80-0
• 化学式: C₁₅H₁₉BrO₂
• 分子量: 311.219
• InChiKey: JPNUXBQEBAKIPC-UHFFFAOYSA-N

物化性质

• 沸点：
  155-162 °C(Press: 0.1 Torr)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  2-[2-(2-溴-5-甲氧基苯基)乙基]环己酮 在 potassium fluoride 、 18-冠醚-6 、 四甲基硅烷 、 对甲苯磺酸 、 六甲基二硅氮烷 、 sodium iodide 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 生成 6-[2-(2-bromo-5-methoxyphenyl)ethyl]-7-(nitromethyl)-1,4-dioxaspiro[4,5]decane
  参考文献：
  名称：

  Synthesis of a compound having the essential structural unit for the hetisine-type of aconite alkaloids

  摘要：

  A hexacyclic compound 1, which carries an almost full structure of the hetisine skeleton lacking only the six-membered ring with an exo methylene group. was synthesized by applying an acetal-ene reaction on 5 for the bond formation of C-14 and C-20 as well as stereoselective hydrocyanation reaction on 7 for construction of the azabicyclo ring system. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00453-7
• 作为产物：
  描述：

  1,1'-联(环己烷)-1'-烯-2-胺 在 水 、 草酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 2-[2-(2-溴-5-甲氧基苯基)乙基]环己酮
  参考文献：
  名称：

  Synthesis of a compound having the essential structural unit for the hetisine-type of aconite alkaloids

  摘要：

  A hexacyclic compound 1, which carries an almost full structure of the hetisine skeleton lacking only the six-membered ring with an exo methylene group. was synthesized by applying an acetal-ene reaction on 5 for the bond formation of C-14 and C-20 as well as stereoselective hydrocyanation reaction on 7 for construction of the azabicyclo ring system. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00453-7

文献信息

• Palladium-catalyzed intramolecular α-arylation of aliphatic ketone, formyl, and nitro groups
  作者：Hideaki Muratake、Mitsutaka Natsume、Hiroshi Nakai

  DOI：10.1016/j.tet.2004.09.112

  日期：2004.12

  Intramolecular arylation of properly designed substrates bearing a ketone, formyl, or nitro terminating group was achieved by use of a PdCl2(Ph3P)2–Cs2CO3 reaction system to form a variety of carbocyclic compounds. Arylation in ketone compounds afforded benzene-annulated bridged or spirocycloalkanone derivatives, depending on the structure of the cyclization precursors. Arylation in formyl compounds

  通过使用PdCl 2（Ph 3 P）2 -Cs 2 CO 3，对设计适当的带有酮，甲酰基或硝基终止基团的底物进行分子内芳构化反应体系形成各种碳环化合物。取决于环化前体的结构，酮化合物中的芳基化可提供苯环化的桥环或螺环烷酮衍生物。取决于环化前体的结构和反应溶剂，甲酰基化合物中的芳基化发生在α位置（α-芳基化）或羰基碳（羰基芳基化）。α-芳基化的仲硝基以Nef反应的方式部分转化为酮，而叔硝基被部分消除，得到苯乙烯型烯烃。
• Enantioselective Construction of Spiro Quaternary Carbon Stereocenters via Pd-Catalyzed Intramolecular α-Arylation
  作者：Ting Wu、Xuehua Kang、Heng Bai、Wenrui Xiong、Guangqing Xu、Wenjun Tang

  DOI：10.1021/acs.orglett.0c01129

  日期：2020.6.19

  We herein report the development of a sterically hindered and electron-rich P-chiral monophosphorus biaryl ligand that has enabled a general and efficient enantioselective intramolecular alpha-arylation, providing access to a wide series of [4.4], [4.5], and [4.6]-spirocycles with chiral benzylic quaternary carbons in high yields with good to excellent enantioselectivities. A pronounced water effect on enantioselectivity is observed.
• Synthesis of Phenanthrenes. III. 5-Methoxy-4a-methyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene
  作者：Roderick A. Barnes、H. Peter Hirschler、Bernard R. Bluestein

  DOI：10.1021/ja01136a037

  日期：1952.8