3-Methyl-1,5-diphenylpent-1-en-4-yn-3-ol | 172363-26-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 3-Methyl-1,5-diphenylpent-1-en-4-yn-3-ol
• 英文别名: 3-methyl-1,5-diphenylpent-1-en-4-yn-3-ol
• CAS: 172363-26-7
• 化学式: C₁₈H₁₆O
• 分子量: 248.324
• InChiKey: AXWUQIDUUZYYRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Methyl-1,5-diphenylpent-1-en-4-yn-3-ol 在 水杨酸 作用下， 以 水 、 乙腈 为溶剂， 反应 16.0h， 以73%的产率得到3-methyl-1,5-diphenylpent-2-en-4-yn-1-ol
  参考文献：
  名称：

  Mild and Tunable Benzoic Acid Catalysts for Rearrangement Reactions of Allylic Alcohols

  摘要：

  An efficient and simple catalytic method for the isomerization of readily prepared allylic alcohols is described. We focus particularly on cyclic examples and the synthesis of unusual enyne and dienols. The benzoic acid catalysts employed are commercially available and very inexpensive and can be tuned for reactivity and substrate sensitivity.

  DOI：

  10.1021/jo201540p
• 作为产物：
  描述：

  苯乙炔 、 苄叉丙酮 在 diethylzinc 、 三乙基铝 、 奎宁 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 61.0h， 生成 3-Methyl-1,5-diphenylpent-1-en-4-yn-3-ol 、 3-Methyl-1,5-diphenylpent-1-en-4-yn-3-ol
  参考文献：
  名称：

  Highly Enantioselective Phenylacetylene Addition to Aromatic Ketones Catalyzed by Cinchona Alkaloid−Aluminum Complexes

  摘要：

  The catalytic asymmetric addition of phenylacetylene to aromatic ketones is reported. The catalyst, generated from commercially available Cinchona alkaloids and industrially available triethylaluminum, gives the expected tertiary alcohols with good enantiomeric excess (70-89%) and yields (60-83%). No previous case has been reported successfully using triethylaluminum as a Lewis acid in the asymmetric alkynylation of carbonylic derivatives, and thus we provide a new method to obtain optically active tertiary propargyl alcohols.

  DOI：

  10.1021/jo0483522

文献信息

• Ruthenium-Catalyzed Synthesis of Highly Substituted Pyrroles from 1-Vinylpropargyl Alcohols and Amines
  作者：Nora Thies、Martin Gerlach、Edgar Haak

  DOI：10.1002/ejoc.201300803

  日期：2013.11

  Ruthenium-catalyzed atom-economic transformations of 1-vinylpropargyl alcohols with amines leading to highly substituted pyrroles in a one-pot cascade process are reported. The allylation/cycloisomerization sequence is catalyzed by a single ruthenium(0) complex that contains a redox-coupled dienone ligand and can be extended by an additional [3,3] rearrangement. The environmentally benign reactions

  报道了钌催化的 1-乙烯基炔丙醇与胺的原子经济转化，导致在一锅级联过程中产生高度取代的吡咯。烯丙基化/环异构化序列由包含氧化还原偶联二烯酮配体的单个钌 (0) 络合物催化，并可通过额外的 [3,3] 重排进行扩展。环境友好的反应允许金属催化将廉价且易于获得的材料转化为高度官能化的吡咯，而水作为唯一的废物产物。
• Ruthenium-Catalyzed Functionalization of Pyrroles and Indoles with Propargyl Alcohols
  作者：Nora Thies、Cristian G. Hrib、Edgar Haak

  DOI：10.1002/chem.201200188

  日期：2012.5.14

  Several ruthenium‐catalyzed atom‐economic transformations of propargyl alcohols with pyrroles or indoles leading to alkylated, propargylated, or annulated heteroaromatics are reported. The mechanistically distinct reactions are catalyzed by a single ruthenium(0) complex containing a redox‐coupled dienone ligand. The mode of activation regarding the propargyl alcohols determines the reaction pathway

  据报道，几种钌催化的炔丙醇与吡咯或吲哚的原子经济转化会导致烷基化，炔丙基化或环化的杂芳族化合物。在机理上截然不同的反应是由包含氧化还原偶联的二烯酮配体的单一钌（0）配合物催化的。关于炔丙醇的活化方式决定了反应途径，并取决于醇的取代方式。次级底物通过1,2-氢转移形成烯基配合物，而第三级底物的转化涉及亚烯基中间体。1-乙烯基炔丙醇通过级联烯丙基化/环化序列转化。
• Mild and Tunable Benzoic Acid Catalysts for Rearrangement Reactions of Allylic Alcohols
  作者：J. Adam McCubbin、Samantha Voth、Oleg V. Krokhin

  DOI：10.1021/jo201540p

  日期：2011.10.21

  An efficient and simple catalytic method for the isomerization of readily prepared allylic alcohols is described. We focus particularly on cyclic examples and the synthesis of unusual enyne and dienols. The benzoic acid catalysts employed are commercially available and very inexpensive and can be tuned for reactivity and substrate sensitivity.
• Highly Enantioselective Phenylacetylene Addition to Aromatic Ketones Catalyzed by Cinchona Alkaloid−Aluminum Complexes
  作者：Lei Liu、Rui Wang、Yong-Feng Kang、Chao Chen、Zhao-Qing Xu、Yi-Feng Zhou、Ming Ni、Hua-Qing Cai、Mao-Zhen Gong

  DOI：10.1021/jo0483522

  日期：2005.2.1

  The catalytic asymmetric addition of phenylacetylene to aromatic ketones is reported. The catalyst, generated from commercially available Cinchona alkaloids and industrially available triethylaluminum, gives the expected tertiary alcohols with good enantiomeric excess (70-89%) and yields (60-83%). No previous case has been reported successfully using triethylaluminum as a Lewis acid in the asymmetric alkynylation of carbonylic derivatives, and thus we provide a new method to obtain optically active tertiary propargyl alcohols.