3,3-dimethyl-1,5-diphenylpent-4-yn-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-dimethyl-1,5-diphenylpent-4-yn-1-one
• 英文别名: 3,3-Dimethyl-1,5-diphenyl-4-pentyne-1-one
• 化学式: C₁₉H₁₈O
• 分子量: 262.351
• InChiKey: ZVJPBVNKHOKJNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,3-dimethyl-1,5-diphenylpent-4-yn-1-one 在 盐酸 、 potassium methanolate 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3,3-dimethyl-1,5-diphenylpentane-1,4-dione
  参考文献：
  名称：

  羰基氧辅助的KOMe介导的4炔酮的正式水合：在温和条件下一锅合成1,4-二酮的完全区域选择性

  摘要：

  在温和的无过渡金属条件下，实现了通过羰基氧协助的4-炔酮正式水合反应，并具有完全区域选择性的便捷高效的合成1,4-二酮的途径。观察到的完全区域选择性得到对照和同位素标记实验的支持。

  DOI：

  10.1002/ejoc.201800024
• 作为产物：
  描述：

  苯乙炔 在 正丁基锂 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 24.0h， 生成 3,3-dimethyl-1,5-diphenylpent-4-yn-1-one
  参考文献：
  名称：

  C ？银催化剂促进二氧化碳与碳键的形成

  摘要：

  催化量的苯甲酸银与7-甲基-1,5,7-三氮杂双环[4.4.0] dec-5-烯（MTBD）的反应是一种有效的催化体系，用于二氧化碳与各种含炔基的酮反应。合适的职位（请参阅计划）。这些反应在温和的条件下以良好或高收率提供了相应的γ-内酯衍生物。

  DOI：

  10.1002/anie.201201399

文献信息

• Copper(II) Triflate-Catalyzed Nucleophilic Substitution of Propargylic Acetates with Enoxysilanes. A Straightforward Synthetic Route to Polysubstituted Furans
  作者：Zhuang-ping Zhan、Shao-pei Wang、Xu-bin Cai、Hui-juan Liu、Jing-liang Yu、Yuan-yuan Cui

  DOI：10.1002/adsc.200700234

  日期：2007.9.3

  A novel and efficient procedure for the synthesis of γ-alkynyl ketones by the nucleophilic substitution of propargylic acetates with enoxysilanes in the presence of a catalytic amount of Copper(II) triflate, has been developed. The substitution reaction can be followed by a 4-toluenesulfonic acid-catalyzed cyclization without purification of the γ-alkynyl ketone intermediates, offering a straightforward

  已经开发了在催化量的三氟甲磺酸铜（II）存在下通过用环氧硅烷的炔丙基乙酸酯的亲核取代合成γ-炔基酮的新颖而有效的方法。取代反应之后可以进行4-甲苯磺酸催化的环化反应，而无需纯化γ-炔基酮中间体，从而提供了直接的合成路线来制备多取代的呋喃。
• Gold-catalyzed cycloisomerization of alk-4-yn-1-ones
  作者：Volker Belting、Norbert Krause

  DOI：10.1039/b819704k

  日期：——

  Depending on the substitution pattern and the solvent, the gold-catalyzed cyclization of alk-4-yn-1-ones 1 affords different oxygen heterocycles under mild reaction conditions. Alkynones with one substituent at C-3 undergo a 5-exo-dig cycloisomerization to substituted furans 2, whereas a 6-endo-digcyclization to 4H-pyrans 3 is observed with substrates bearing two substituents at C-3. In alcoholic solvents

  根据取代方式和溶剂的不同，在轻度的反应条件下，alk-4-yn-1-ones 1的金催化环化反应会产生不同的氧杂环。与C-3一个取代基Alkynones经过5 -外型-挖环异构取代的呋喃2，而6 -内-挖环化成4 ħ -pyrans 3与基板承载两个取代基在C-3观察到。在醇溶剂中，以串联亲核加成/环异构化反应形成亚烷基/亚苄基取代的四氢呋喃基醚4。
• FeCl₃-Catalyzed Nucleophilic Substitution of Propargylic Acetates with Enoxysilanes
  作者：Zhuang-ping Zhan、Xu-bin Cai、Shao-pei Wang、Jing-liang Yu、Hui-juan Liu、Yuan-yuan Cui

  DOI：10.1021/jo701782g

  日期：2007.12.1

  [Graphics]An efficient FeCl3-catalyzed substitution reaction of propargylic acetates with enoxysilanes under mild conditions to afford corresponding gamma-alkynyl ketones has been developed. The substitution reaction is followed by a TsOH-catalyzed cyclization without purification of the gamma-alkynyl ketone intermediates, offering a straightforward synthetic route to tri- or tetrasubstituted furans.
• Gold-Catalyzed Cycloisomerization of 1,6-Diyne Carbonates and Esters to 2,4a-Dihydro-1<i>H</i>-fluorenes
  作者：Weidong Rao、Ming Joo Koh、Dan Li、Hajime Hirao、Philip Wai Hong Chan

  DOI：10.1021/ja4032727

  日期：2013.5.29

  A synthetic method to prepare 2,4a-dihydro-1H-fluorenes efficiently from gold(I)-catalyzed 1,2-acyloxy migration/cyclopropenation/Nazarov cyclization of 1,6-diyne carbonates and esters is described. The suggested reaction pathway provides rare examples of [2,3]-sigmatropic rearrangement in this class of compounds as well as the involvement of an in situ formed cyclopropene intermediate in gold catalysis. Experimental and ONIOM(QM:QM') [our own n-layered integrated molecular orbital and molecular mechanics(quantum mechanics quantum mechanics')] computational studies based on the proposed Au carbenoid species provide insight into this unique selectivity.
• Cyclopentanone as a Cation-Stabilizing Electron-Pair Donor in the Calcium-Catalyzed Intermolecular Carbohydroxylation of Alkynes
  作者：Tobias Stopka、Meike Niggemann

  DOI：10.1021/acs.orglett.5b00312

  日期：2015.3.20

  Although they have been used as reactivity-controlling additives in cationic polymerizations for decades, Lewis basic electron pair donor (ED) compounds were never used for the stabilization of cationic intermediates in transformations of small molecules. As such an ED, cyclopentanone proved highly efficient for the stabilization of allyl and vinyl cations in combination with our calcium-based catalyst system. Therefore, the first general transition-metal-free intermolecular carbohydroxylation of alkynes with allyl and propargyl alcohols was realized.