5,5-dimethyl-3-(5-phenylpent-4-yn-1-yl)cyclohex-2-en-1-one | 1404440-60-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5-dimethyl-3-(5-phenylpent-4-yn-1-yl)cyclohex-2-en-1-one
• 英文别名: 5,5-Dimethyl-3-(5-phenylpent-4-ynyl)cyclohex-2-en-1-one；5,5-dimethyl-3-(5-phenylpent-4-ynyl)cyclohex-2-en-1-one
• CAS: 1404440-60-3
• 化学式: C₁₉H₂₂O
• 分子量: 266.383
• InChiKey: XRTZVKRAKNKHHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  5,5-dimethyl-3-(5-phenylpent-4-yn-1-yl)cyclohex-2-en-1-one 在 sodium tetrahydroborate 、 2-iodoxybenzoic acid 、 cerium(III) chloride heptahydrate 、 diethylzinc 作用下， 以 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 13.33h， 生成 (±)-(1S,6R)-4,4-dimethyl-6-(5-phenylpent-4-yn-1-yl)-bicyclo[4.1.0]heptan-2-one
  参考文献：
  名称：

  Synthesis of 2-Azaspiro[4.6]undec-7-enes from N-Tosyl-N-(3-arylpropargyl)-Tethered 3-Methylcyclohex-2-en-1-ols

  摘要：

  The FeCl3-promoted synthesis of 2-azaspiro[4.6]-undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3-arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl-protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.

  DOI：

  10.1021/jo301764g
• 作为产物：
  描述：

  3-methoxy-5,5-dimethyl-cyclohex-2-enone 、 (5-iodopent-1-yn-1-yl)benzene 在 叔丁基锂 作用下， 以 乙醚 为溶剂， 反应 13.0h， 生成 5,5-dimethyl-3-(5-phenylpent-4-yn-1-yl)cyclohex-2-en-1-one
  参考文献：
  名称：

  Synthesis of 2-Azaspiro[4.6]undec-7-enes from N-Tosyl-N-(3-arylpropargyl)-Tethered 3-Methylcyclohex-2-en-1-ols

  摘要：

  The FeCl3-promoted synthesis of 2-azaspiro[4.6]-undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3-arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl-protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.

  DOI：

  10.1021/jo301764g

文献信息

• Synthesis of 2-Azaspiro[4.6]undec-7-enes from <i>N</i>-Tosyl-<i>N</i>-(3-arylpropargyl)-Tethered 3-Methylcyclohex-2-en-1-ols
  作者：Ming-Chang P. Yeh、Chia-Jung Liang、Chern-Wei Fan、Wei-Hang Chiu、Jun-Yuan Lo

  DOI：10.1021/jo301764g

  日期：2012.11.2

  The FeCl3-promoted synthesis of 2-azaspiro[4.6]-undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3-arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl-protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.