2-methyl-2-(4-methylpent-3-enyl)-6,7-dihydro-2H-chromen-5(3H)-one | 1236034-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-methyl-2-(4-methylpent-3-enyl)-6,7-dihydro-2H-chromen-5(3H)-one
• 英文别名: 2-methyl-2-(4-methylpent-3-enyl)-6,7-dihydro-3H-chromen-5-one
• CAS: 1236034-15-3；1236034-34-6
• 化学式: C₁₆H₂₂O₂
• 分子量: 246.349
• InChiKey: KVUHODMRKKVWIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-2-(3,7-dimethylocta-2,6-dienyl)-3-hydroxycyclohex-2-enone 在 (M,3aS,3a'S)-3,3',3a',4,4',5,5'-octahydro-3,3,3',3'-tetraisopropyl-6,6'-spirobi[6H-cyclopent[c]isoxazole] 、 双(乙腈)氯化钯(II) 、 对苯醌 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 12.0h， 以12%的产率得到2-methyl-2-(4-methylpent-3-enyl)-6,7-dihydro-2H-chromen-5(3H)-one
  参考文献：
  名称：

  Enantioselective Wacker-Type Cyclization of 2-Alkenyl-1,3-diketones Promoted by Pd-SPRIX Catalyst

  摘要：

  An enantioselective intramolecular Wacker-type cyclization of 2-alkenyl-1,3-diketones catalyzed by a Pd(II)-SPRIX complex was developed. The reaction proceeded in a 6-endo-trig mode to give the desired chromene derivatives with moderate to good enantioselectivity. Isomerization of C-C double bonds via a pi-allyl Pd intermediate was involved as the key step.

  DOI：

  10.1021/ol1013069

文献信息

• Enantioselective Wacker-Type Cyclization of 2-Alkenyl-1,3-diketones Promoted by Pd-SPRIX Catalyst
  作者：Kazuhiro Takenaka、Suman C. Mohanta、Mahesh L. Patil、C. V. Laxman Rao、Shinobu Takizawa、Takeyuki Suzuki、Hiroaki Sasai

  DOI：10.1021/ol1013069

  日期：2010.8.6

  An enantioselective intramolecular Wacker-type cyclization of 2-alkenyl-1,3-diketones catalyzed by a Pd(II)-SPRIX complex was developed. The reaction proceeded in a 6-endo-trig mode to give the desired chromene derivatives with moderate to good enantioselectivity. Isomerization of C-C double bonds via a pi-allyl Pd intermediate was involved as the key step.