(+/-)-5-hydroxy-5-(4-methoxyphenyl)pent-1-en-3-one | 872427-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-5-hydroxy-5-(4-methoxyphenyl)pent-1-en-3-one
• 英文别名: 5-Hydroxy-5-(4-methoxyphenyl)pent-1-en-3-one；5-hydroxy-5-(4-methoxyphenyl)pent-1-en-3-one
• CAS: 872427-99-1
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: WBCVTDRSIZSEIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-5-hydroxy-5-(4-methoxyphenyl)pent-1-en-3-one 、 1-十二烯十二碳烯α-十二碳烯α-十二碳烯 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到(+/-)-(E)-1-hydroxy-1-(4-methoxyphenyl)pentadec-4-en-3-one
  参考文献：
  名称：

  Elongation of β-hydroxyenones by cross-metathesis

  摘要：

  Enantioenriched aldol products derived from enones are notoriously difficult to prepare due to their sensitivity to retroaldolisation, elimination and the requirement of a large excess of the enone donor for their preparation. However, some success has been obtained for the preparation of aldol products derived from methylvinylketone and penterione using zinc-dinuclear catalysts or catalytic antibodies. Herein, we describe how simple first-generation hydroxyenones can be easily elongated by alkene exchange with structurally diverse olefinic partners in the presence of Ru-based metathesis catalysts allowing for the preparation of aldol products difficult to access by direct aldolisation. The data suggest that even though unprotected aldols are suitable for these cross-metatbesis reactions, silyl-protected beta-hydroxyenones generally afforded the desired elongated products in much higher chemical yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.037
• 作为产物：
  描述：

  (+/-)-ethyl 3-hydroxy-3-(4-methoxyphenyl)propanoate 在 三甲基铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.83h， 生成 (+/-)-5-hydroxy-5-(4-methoxyphenyl)pent-1-en-3-one
  参考文献：
  名称：

  Elongation of β-hydroxyenones by cross-metathesis

  摘要：

  Enantioenriched aldol products derived from enones are notoriously difficult to prepare due to their sensitivity to retroaldolisation, elimination and the requirement of a large excess of the enone donor for their preparation. However, some success has been obtained for the preparation of aldol products derived from methylvinylketone and penterione using zinc-dinuclear catalysts or catalytic antibodies. Herein, we describe how simple first-generation hydroxyenones can be easily elongated by alkene exchange with structurally diverse olefinic partners in the presence of Ru-based metathesis catalysts allowing for the preparation of aldol products difficult to access by direct aldolisation. The data suggest that even though unprotected aldols are suitable for these cross-metatbesis reactions, silyl-protected beta-hydroxyenones generally afforded the desired elongated products in much higher chemical yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.037

文献信息

• Elongation of β-hydroxyenones by cross-metathesis
  作者：Franck A. Silva、Véronique Gouverneur

  DOI：10.1016/j.tetlet.2005.10.037

  日期：2005.12

  Enantioenriched aldol products derived from enones are notoriously difficult to prepare due to their sensitivity to retroaldolisation, elimination and the requirement of a large excess of the enone donor for their preparation. However, some success has been obtained for the preparation of aldol products derived from methylvinylketone and penterione using zinc-dinuclear catalysts or catalytic antibodies. Herein, we describe how simple first-generation hydroxyenones can be easily elongated by alkene exchange with structurally diverse olefinic partners in the presence of Ru-based metathesis catalysts allowing for the preparation of aldol products difficult to access by direct aldolisation. The data suggest that even though unprotected aldols are suitable for these cross-metatbesis reactions, silyl-protected beta-hydroxyenones generally afforded the desired elongated products in much higher chemical yields. (c) 2005 Elsevier Ltd. All rights reserved.