ethyl 1-(2-bromo-2-propenyl)-2-oxocyclohexanecarboxylate | 133550-61-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 1-(2-bromo-2-propenyl)-2-oxocyclohexanecarboxylate
• 英文别名: 1-(2-bromoallyl)-2-oxocyclohexanecarboxylic acid ethyl ester；Ethyl 1-(2-bromoprop-2-enyl)-2-oxocyclohexane-1-carboxylate
• CAS: 133550-61-5
• 化学式: C₁₂H₁₇BrO₃
• 分子量: 289.169
• InChiKey: QLSKUHFQSXYXNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-(2-bromo-2-propenyl)-2-oxocyclohexanecarboxylate 在 sodium tetrahydroborate 、 cerium(III) chloride 、 草酰氯 、 偶氮二异丁腈 、 三正丁基氢锡 、 二甲基亚砜 、 三乙胺 、 calcium carbonate 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 75.83h， 生成 ethyl 5-methylene-2-oxo-bicyclo<2.2.2>octane-1-carboxylate
  参考文献：
  名称：

  Vinyl radical cyclizations: synthesis of substituted bicyclooctanols

  摘要：

  The preparation and free-radical bicyclic ring closure of 4-(2-bromo-2-propen-1-yl)cyclohexene 7 is described. The bicyclo[3.2.1] and -[2.2.2] alcohols 9 and 10 arising, respectively, from 5-exo and 6-endo (or 6-exo) modes of cyclization of a vinyl radical were isolated in a 1:1 ratio. Factors affecting the regiochemical outcome were investigated.

  DOI：

  10.1021/jo00009a032
• 作为产物：
  描述：

  2-环己酮甲酸乙酯 、 2,3-二溴-1-丙烯 在 sodium hydride 作用下， 生成 ethyl 1-(2-bromo-2-propenyl)-2-oxocyclohexanecarboxylate
  参考文献：
  名称：

  Vinyl radical cyclizations: synthesis of substituted bicyclooctanols

  摘要：

  The preparation and free-radical bicyclic ring closure of 4-(2-bromo-2-propen-1-yl)cyclohexene 7 is described. The bicyclo[3.2.1] and -[2.2.2] alcohols 9 and 10 arising, respectively, from 5-exo and 6-endo (or 6-exo) modes of cyclization of a vinyl radical were isolated in a 1:1 ratio. Factors affecting the regiochemical outcome were investigated.

  DOI：

  10.1021/jo00009a032

文献信息

• A Mild, Convenient, and Inexpensive Procedure for Conversion of Vinyl Halides to α-Haloketones
  作者：Michael P. VanBrunt、Reuben O. Ambenge、Steven M. Weinreb

  DOI：10.1021/jo020739m

  日期：2003.4.1

  to the corresponding alpha-chloroketone. Similarly, if a vinyl bromide is exposed to sodium hypobromite (freshly prepared from bromine and sodium hydroxide) at 0 degrees C in 2:5 acetic acid/acetone as solvent, an alpha-bromoketone is produced. This methodology has been applied to a number of vinyl chlorides and vinyl bromides, and the transformations generally proceed in high yields. The mild reaction

  用市售的次氯酸钠水溶液在乙酸/丙酮的2：5混合物中于0摄氏度下处理氯乙烯约1小时，可干净地得到相应的α-氯酮。类似地，如果将溴化乙烯在0摄氏度于2：5乙酸/丙酮作为溶剂中暴露于次溴酸钠（由溴和氢氧化钠新制）中，则会制得α-溴代酮。该方法已经应用于许多氯乙烯和溴乙烯，并且转化通常以高收率进行。温和的反应条件与各种官能团兼容，包括酰胺，酯和亚胺。
• BERKOWITZ, WILLIAM F.;WILSON, PHYLLIS J., J. ORG. CHEM., 56,(1991) N, C. 3097-3102
  作者：BERKOWITZ, WILLIAM F.、WILSON, PHYLLIS J.

  DOI：——

  日期：——
• Vinyl radical cyclizations: synthesis of substituted bicyclooctanols
  作者：William F. Berkowitz、Phyllis J. Wilson

  DOI：10.1021/jo00009a032

  日期：1991.4

  The preparation and free-radical bicyclic ring closure of 4-(2-bromo-2-propen-1-yl)cyclohexene 7 is described. The bicyclo[3.2.1] and -[2.2.2] alcohols 9 and 10 arising, respectively, from 5-exo and 6-endo (or 6-exo) modes of cyclization of a vinyl radical were isolated in a 1:1 ratio. Factors affecting the regiochemical outcome were investigated.