2-(Chloromethyl)-6-methoxy-3,5-dimethylpyran-4-one | 908333-84-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-(Chloromethyl)-6-methoxy-3,5-dimethylpyran-4-one
• CAS: 908333-84-6
• 化学式: C₉H₁₁ClO₃
• 分子量: 202.638
• InChiKey: KQPNSSGXDUCQOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  327.8±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(Chloromethyl)-6-methoxy-3,5-dimethylpyran-4-one 在 camphor-10-sulfonic acid 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 30.0h， 生成 2-[(1E,5E,7E,9R,10R,11E)-10-hydroxy-3-methoxy-3,7,9,11-tetramethyltrideca-1,5,7,11-tetraenyl]-6-methoxy-3,5-dimethylpyran-4-one
  参考文献：
  名称：

  The first total synthesis and structural determination of actinopyrone A

  摘要：

  Actinopyrone A (1) has been synthesized by using our developed remote stereoinduction, Kocienski olefination, Horner-Wadsworth-Emmons olefination, and reductive de-conjugation of the vinylpyrone. A concise method of O-methylation to obtain the gamma-pyrone has also been established. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.028
• 作为产物：
  描述：

  4-hydroxy-3,5,6-trimethyl-2H-pyran-2-one 在 N-氯代丁二酰亚胺 、 calcium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 73.0h， 生成 2-(Chloromethyl)-6-methoxy-3,5-dimethylpyran-4-one
  参考文献：
  名称：

  The first total synthesis and structural determination of actinopyrone A

  摘要：

  Actinopyrone A (1) has been synthesized by using our developed remote stereoinduction, Kocienski olefination, Horner-Wadsworth-Emmons olefination, and reductive de-conjugation of the vinylpyrone. A concise method of O-methylation to obtain the gamma-pyrone has also been established. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.028

文献信息

• Carboalumination/Ni-catalyzed couplings. A short synthesis of verticipyrone
  作者：Bruce H. Lipshutz、Benjamin Amorelli

  DOI：10.1016/j.tetlet.2009.02.167

  日期：2009.5

  Verticipyrone (1) has been synthesized in six overall steps from commercially available ethyl-2-methylacetoacetate. This represents the first successful application of a modified Negishi carboalumination nickel-catalyzed cross-coupling reaction to a chloromethylated pyrone. (C) 2009 Elsevier Ltd. All rights reserved.