4-hydroxy-3-methylene-6-phenylhex-5-yn-2-one | 596135-75-0

• 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: 4-hydroxy-3-methylene-6-phenylhex-5-yn-2-one
• 英文别名: 4-Hydroxy-3-methylidene-6-phenylhex-5-yn-2-one；4-hydroxy-3-methylidene-6-phenylhex-5-yn-2-one
• CAS: 596135-75-0
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: WZTPOWWQNOUWAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  359.2±42.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  乙酸酐 、 4-hydroxy-3-methylene-6-phenylhex-5-yn-2-one 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以80%的产率得到4-methylene-5-oxo-1-phenylhex-1-yn-3-yl acetate
  参考文献：
  名称：

  3,5-Disubstituted 6H-pyrrolo[1,2-c][1,2,3]triazoles from Morita–Baylis–Hillman adducts of propargyl aldehydes

  摘要：

  A simple method for synthesizing several 6H-pyrrolo[1,2-c][1,2,3]triazole derivatives having a methoxy carbonyl or an acetyl group at C-5 position and 7,8-dihydro-4H-[1,2,3]triazolo[1,5-a]indol-5(6H)-ones via an intramolecular 1,3-dipolar cycloaddition reaction of azido enynes, which were readily obtained from the Morita-Baylis-Hillman acetates of propargyl aldehydes with sodium azide, has been developed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.017
• 作为产物：
  描述：

  3-苯基-2-丙炔-1-醇 在 三乙烯二胺 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 15.0h， 生成 4-hydroxy-3-methylene-6-phenylhex-5-yn-2-one
  参考文献：
  名称：

  乙炔醛在Baylis–Hillman反应中的使用：多功能烯丙基炔丙醇的合成

  摘要：

  据报道，炔醛在Baylis-Hillman反应中的应用使烯丙基炔丙醇的产率中等至良好。

  DOI：

  10.1016/s0040-4039(03)01169-9

文献信息

• Krishna, Palakodety Radha; Sekhar, Empati Raja; Kannan, Synthesis, 2004, # 6, p. 857 - 860
  作者：Krishna, Palakodety Radha、Sekhar, Empati Raja、Kannan

  DOI：——

  日期：——
• Sulpholane––A new solvent for the Baylis–Hillman reaction
  作者：Palakodety Radha Krishna、A. Manjuvani、V. Kannan、G.V.M. Sharma

  DOI：10.1016/j.tetlet.2003.11.137

  日期：2004.2

  Sulpholane, a commercially available solvent, is used for the first time as a new solvent for the Baylis-Hillman reaction tinder ambient conditions; a wide variety of olefins as well as aldehydes participate very efficiently resulting in good to excellent yields of products. Acrylamide also underwent the Baylis-Hillman reaction with 4-nitrobenzaldehyde under these reaction conditions. (C) 2003 Elsevier Ltd. All rights reserved.
• The use of acetylenic aldehydes in Baylis–Hillman reactions: synthesis of versatile allyl propargyl alcohols
  作者：Palakodety Radha Krishna、Empati Raja Sekhar、V. Kannan

  DOI：10.1016/s0040-4039(03)01169-9

  日期：2003.6

  The utility of acetylenic aldehydes in Baylis–Hillman reactions giving allyl propargyl alcohols in moderate to good yields is reported.

  据报道，炔醛在Baylis-Hillman反应中的应用使烯丙基炔丙醇的产率中等至良好。
• 3,5-Disubstituted 6H-pyrrolo[1,2-c][1,2,3]triazoles from Morita–Baylis–Hillman adducts of propargyl aldehydes
  作者：Sun Pil Park、Sang-Hyun Ahn、Kee-Jung Lee

  DOI：10.1016/j.tet.2010.03.017

  日期：2010.5

  A simple method for synthesizing several 6H-pyrrolo[1,2-c][1,2,3]triazole derivatives having a methoxy carbonyl or an acetyl group at C-5 position and 7,8-dihydro-4H-[1,2,3]triazolo[1,5-a]indol-5(6H)-ones via an intramolecular 1,3-dipolar cycloaddition reaction of azido enynes, which were readily obtained from the Morita-Baylis-Hillman acetates of propargyl aldehydes with sodium azide, has been developed. (C) 2010 Elsevier Ltd. All rights reserved.