1-Hydroxy-4-phenylbut-3-yn-2-one | 1219685-01-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-Hydroxy-4-phenylbut-3-yn-2-one
• CAS: 1219685-01-4
• 化学式: C₁₀H₈O₂
• 分子量: 160.172
• InChiKey: WWMYNLAHHKWNBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  1-Hydroxy-4-phenylbut-3-yn-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以87%的产率得到4-(phenyl)but-3-yne-1,2-diol
  参考文献：
  名称：

  Cationic Gold(I)-Mediated Intramolecular Cyclization of 3-Alkyne-1,2-diols and 1-Amino-3-alkyn-2-ols: A Practical Route to Furans and Pyrroles

  摘要：

  The intramolecular cyclizations of the 3-alkyne-1,2-diols and the 1-amino-3-alkyn-2-ols with a low catalyst loading (0.05-0.5 mol %) of (Ph3P)AuCl-AgNTf2 or (Ph3P)AuCl-AgOTf proceeded at room temperature to provide a variety of substituted furans and pyrroles in excellent yields (85-98% yields). This method is also fully applicable to the conversion of several dozen grams of the substrate using only 0.05 mol % each of the Au and Ag catalysts.

  DOI：

  10.1021/ol901942t
• 作为产物：
  描述：

  1-(tert-butyl-dimethyl-silanyloxy)-4-phenyl-but-3-yn-2-one 在 吡啶 、 氢氟酸 、 水 、 氯化铵 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以80%的产率得到1-Hydroxy-4-phenylbut-3-yn-2-one
  参考文献：
  名称：

  Cationic Gold(I)-Mediated Intramolecular Cyclization of 3-Alkyne-1,2-diols and 1-Amino-3-alkyn-2-ols: A Practical Route to Furans and Pyrroles

  摘要：

  The intramolecular cyclizations of the 3-alkyne-1,2-diols and the 1-amino-3-alkyn-2-ols with a low catalyst loading (0.05-0.5 mol %) of (Ph3P)AuCl-AgNTf2 or (Ph3P)AuCl-AgOTf proceeded at room temperature to provide a variety of substituted furans and pyrroles in excellent yields (85-98% yields). This method is also fully applicable to the conversion of several dozen grams of the substrate using only 0.05 mol % each of the Au and Ag catalysts.

  DOI：

  10.1021/ol901942t

文献信息

• Asymmetric Catalytic [4+5] Annulation of <i>ortho</i> ‐Quinone Methides with Vinylethylene Carbonates and its Extension to Stereoselective Tandem Rearrangement
  作者：Xian‐Tao An、Ji‐Yuan Du、Zhi‐Long Jia、Qing Zhang、Ke‐Yin Yu、Yi‐Zhou Zhang、Xian‐He Zhao、Ran Fang、Chun‐An Fan

  DOI：10.1002/chem.201904903

  日期：2020.3.23

  this designed [4+5] annulation, an unprecedented silica gel-promoted tandem rearrangement reaction featuring a unique asymmetric aromatic Claisen rearrangement is explored at room temperature, offering a new method for asymmetric construction of all-carbon quaternary stereocenters embedded in chiral functionalized homoallylic alcohols.

  首次描述了钯催化的邻醌甲基化物（o-QM）与取代的碳酸乙烯基亚乙酯（VEC）的不对称[4 + 5]环化反应，为手性九元苯并杂环提供了新颖的对映选择性方法。基于这种设计的[4 + 5]环空，在室温下探索了前所未有的硅胶促进的串联重排反应，该反应具有独特的不对称芳族克莱森重排，为嵌入手性官能化的全碳四元立体中心的不对称构建提供了新方法均烯丙基醇。
• An Ir/Zn Dual Catalysis for Enantio- and Diastereodivergent α-Allylation of α-Hydroxyketones
  作者：Xiaohong Huo、Rui He、Xiao Zhang、Wanbin Zhang

  DOI：10.1021/jacs.6b06156

  日期：2016.9.7

  An Ir/Zn dual catalysis has been developed for the enantio- and diastereodivergent alpha-allylation of unprotected alpha-hydroxyketones under mild conditions, in the absence of any additional base. The cooperative action of a chiral iridium complex derived from phosphoramidites and a chiral Zn-ProPhenol complex is most likely responsible for its high reactivity, excellent enantioselectivity (up to >99% ee), and good diastereoselectivity (up to >20:1 dr). All four product stereoisomers could be prepared from the same set of starting materials and under identical conditions by simple selection of appropriate catalyst combinations.