2-[(2-bromophenyl)methyl]-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one | 1407096-37-0

• 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-[(2-bromophenyl)methyl]-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one
• 英文别名: 2-[(2-Bromophenyl)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one；2-[(2-bromophenyl)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
• CAS: 1407096-37-0
• 化学式: C₁₅H₁₇BrO₂
• 分子量: 309.203
• InChiKey: FKXMPYBPSGYUAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(2-bromophenyl)methyl]-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one 在 caesium carbonate 、 三甲基丙酮酸 、 copper(l) chloride 作用下， 反应 7.0h， 以98%的产率得到3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one
  参考文献：
  名称：

  Copper(I)-Catalyzed Intramolecular O-Arylation for the Synthesis of 2,3,4,9-Tetrahydro-1H-xanthen-1-ones with Low Loads of CuCl

  摘要：

  As little as 0.5 mol % CuCl is sufficient to catalyze the intramolecular O-arylation of easily accessible 2-(2-bromobenzyl)cyclohexane-1,3-diones to provide the corresponding 2,3,4,9-tetrahydro-1H-xanthen-1-ones with yields ranging from 83% to 99%.

  DOI：

  10.1021/jo3018318
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 2-溴溴苄 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以68%的产率得到2-[(2-bromophenyl)methyl]-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one
  参考文献：
  名称：

  Copper(I)-Catalyzed Intramolecular O-Arylation for the Synthesis of 2,3,4,9-Tetrahydro-1H-xanthen-1-ones with Low Loads of CuCl

  摘要：

  As little as 0.5 mol % CuCl is sufficient to catalyze the intramolecular O-arylation of easily accessible 2-(2-bromobenzyl)cyclohexane-1,3-diones to provide the corresponding 2,3,4,9-tetrahydro-1H-xanthen-1-ones with yields ranging from 83% to 99%.

  DOI：

  10.1021/jo3018318

文献信息

• Copper(I)-Catalyzed Intramolecular O-Arylation for the Synthesis of 2,3,4,9-Tetrahydro-1<i>H</i>-xanthen-1-ones with Low Loads of CuCl
  作者：Kavitha Sudheendran、Chandi C. Malakar、Jürgen Conrad、Uwe Beifuss

  DOI：10.1021/jo3018318

  日期：2012.11.16

  As little as 0.5 mol % CuCl is sufficient to catalyze the intramolecular O-arylation of easily accessible 2-(2-bromobenzyl)cyclohexane-1,3-diones to provide the corresponding 2,3,4,9-tetrahydro-1H-xanthen-1-ones with yields ranging from 83% to 99%.
• Copper-Catalysed One-Pot Synthesis of 2,3,4,9-Tetrahydro-1H-Xanthen-1-Ones from 2-Halobenzylbromides and Cyclic-1,3-Diketones in Water
  作者：Zuxing Mao、Xinhai Zhu、Yiqian Wan

  DOI：10.1007/s10562-015-1538-z

  日期：2015.8

  A simple, environmentally friendly, tandem C-benzylation and intramolecular O-arylation for the sequential one-pot synthesis of functionalised 4H-chromenes is reported. The reactions between 2-halobenzylbromides and cyclic-1,3-diketones were catalysed by CuO/oxalohydrazide/hexane-2,5-dione in water to produce 2,3,4,9-tetrahydro-1H-xanthen-1-ones in moderate to high yields.A simple, environmental friendly, tandem C-benzylation and intramolecular O-arylation for the sequential one-pot synthesis of 2,3,4,9-tetrahydro-1H-xanthen-1-ones in water is described.