3-(hydroxy(naphthalen-2-yl)methyl)but-3-en-2-one | 849900-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(hydroxy(naphthalen-2-yl)methyl)but-3-en-2-one
• 英文别名: 4-hydroxy-3-methylene-4-(2-naphthyl)butan-2-one；3-[Hydroxy(naphthalen-2-yl)methyl]but-3-en-2-one
• CAS: 849900-45-4
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: PONBQNYVIMSJPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  苯亚磺酰氯 、 3-(hydroxy(naphthalen-2-yl)methyl)but-3-en-2-one 以 氯仿 为溶剂， 反应 30.0h， 以72%的产率得到(Z)-3-(benzenesulfonylmethyl)-4-naphthalen-2-ylbut-3-en-2-one
  参考文献：
  名称：

  An Expeditious Entry to Benzylic and Allylic Sulfones through Byproduct-Catalyzed Reaction of Alcohols with Sulfinyl Chlorides

  摘要：

  In the absence of external catalysts and additives, a broad range of benzylic and allylic alcohols react with various sulfinyl chlorides to afford structurally diversified benzylic and allylic sulfones in moderate to excellent yields, and importantly, a catalysis with byproduct HCl is involved in this new protocol for sulfone synthesis.

  DOI：

  10.1021/jo901974h
• 作为产物：
  描述：

  丁烯酮 、 2-萘甲醛 在 四氢噻吩 、 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 3-(hydroxy(naphthalen-2-yl)methyl)but-3-en-2-one
  参考文献：
  名称：

  Morita–Baylis–Hillman加合物的氢化铜还原反应中化学，区域和对映选择性的控制

  摘要：

  非消旋连接的氢化铜可用于串联S N 2'/ 1,2-还原外消旋的森田-贝利斯-希尔曼（MBH）乙酸酯，以得到具有定义的烯烃几何形状的对映体富集的手性烯丙基醇。MBH酯（包括具有β取代基的酯）可以利用庞大的，低聚的，原位生成的三烷氧基硅氧烷离去基团转化为立体定义的烯酸酯。最后，公开了容易到达的MBH醇衍生物向非外消旋烯丙基醇的非典型转化。

  DOI：

  10.1021/acs.orglett.6b03464

文献信息

• Morita-Baylis-Hillman Reaction on Water without Organic Solvent, Assisted by a ‘Catalytic’ Amount of Amphiphilic Imidazole Derivatives
  作者：Seijiro Matsubara、Keisuke Asano

  DOI：10.1055/s-0029-1216944

  日期：2009.10

  A Morita-Baylis-Hillman (MBH) reaction using water as a solvent without any organic solvent can be performed by using an amphiphilic N-alkylimidazole. This reaction is accelerated by the addition of water and is the first example of a ‘catalytic’ MBH reaction without organic solvent in the presence of water.

  可以使用两性N-烷基咪唑在无任何有机溶剂的情况下，以水作为溶剂进行Morita-Baylis-Hillman (MBH)反应。随着水的添加，该反应得以加速，这是在水存在下进行的第一个没有有机溶剂的“催化”MBH反应的例子。
• <i>N</i>-Alkylimidazole as Amphiphilic Organocatalyst: ‘Catalytic’ Morita-Baylis-Hillman Reaction on Water without Organic Solvent
  作者：Seijiro Matsubara、Keisuke Asano

  DOI：10.1055/s-0028-1087484

  日期：——

  In the presence of water, a Morita-Baylis-Hillman reaction between methyl vinyl ketone and various aldehydes was performed with a catalytic amount of an imidazole carrying a hydrophobic group.

  在有水的情况下，甲基乙烯基酮和各种醛在带有疏水基团的咪唑催化下发生了 Morita-Baylis-Hillman 反应。
• 1-Methylimidazole 3-N-oxide as a new promoter for the Morita–Baylis–Hillman reaction
  作者：Yu-Sheng Lin、Chih-Wei Liu、Thomas Y.R. Tsai

  DOI：10.1016/j.tetlet.2005.01.099

  日期：2005.3

  The Morita-Baylis-Hillman reaction of aldehydes with alpha,beta-unsaturated ketones can be affected by the Lewis bases. We have found that 1-methylimidazole 3-N-oxide promoted the Morita-Baylis-Hiliman reaction of various activated aldehyde compounds in non-solvent system. This is a mild reaction condition and requires no special equipment to give the Morita-BaylisHillman adducts. (C) 2005 Elsevier Ltd. All rights reserved.
• A highly active ionic liquid catalyst for Morita–Baylis–Hillman reaction
  作者：Yu-Sheng Lin、Chiao-Yang Lin、Chih-Wei Liu、Thomas Y.R. Tsai

  DOI：10.1016/j.tet.2005.10.048

  日期：2006.1

  The Morita-Baylis-Hillman reaction is an efficient carbon-carbon bond forming reaction for the preparation of alpha-methylene-beta-hydroxycarbonyl compounds. A new and highly active di-naphthalene imidazolium salt has been synthesized. We have found that 1, 3-bis[2-(naphthalene-2-yloxy)propyl]imidazolium bromid promoted the Morita-Baylis-Hillman reaction of various aryl aldehyde compounds in the absence of solvents. Our studies show that the Morita-Baylis-Hillman reaction by the influence of ionic liquid to give a high yield and short reaction time. (c) 2005 Elsevier Ltd. All rights reserved.
• An Expeditious Entry to Benzylic and Allylic Sulfones through Byproduct-Catalyzed Reaction of Alcohols with Sulfinyl Chlorides
  作者：Hai-Hua Li、De-Jun Dong、Yin-Huan Jin、Shi-Kai Tian

  DOI：10.1021/jo901974h

  日期：2009.12.18

  In the absence of external catalysts and additives, a broad range of benzylic and allylic alcohols react with various sulfinyl chlorides to afford structurally diversified benzylic and allylic sulfones in moderate to excellent yields, and importantly, a catalysis with byproduct HCl is involved in this new protocol for sulfone synthesis.