1,3,3,5-tetraphenylpent-4-yn-1-one

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 1,3,3,5-tetraphenylpent-4-yn-1-one
• 英文别名: 1,4,4,6-tetraphenylpent-4-yn-2-one；1,3,3,5-Tetraphenylpent-4-yn-1-one
• 化学式: C₂₉H₂₂O
• 分子量: 386.493
• InChiKey: DGOKNJSBFNFPFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 3-乙酰氧基-1,3,3-三苯基丙炔 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以52%的产率得到1,3,3,5-tetraphenylpenta-3,4-dien-1-one
  参考文献：
  名称：

  三氟甲磺酸铜（II）催化丙炔基乙酸酯与亲氧基硅烷的亲核取代。直接合成多取代呋喃的合成路线

  摘要：

  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。

  DOI：

  10.1002/adsc.200700234

文献信息

• Ir-Catalyzed Substitution of Propargylic-type Esters with Enoxysilanes
  作者：Isamu Matsuda、Ken-ichi Komori、Kenji Itoh

  DOI：10.1021/ja0264089

  日期：2002.8.1

  Propargylic-type acetates react readily with enoxysilanes in the presence of 1 mol % of [Ir(cod)P(OPh)3}2]OTf activated preliminarily with molecular H2 to give beta-alkynyl ketones in high to excellent yields. Substitution at the propargyl carbon proceeds exclusively or selectively in most types of propargylic esters. Alternatively, the formation of the allenyl products is predominant in the reaction of esters, which have two phenyl groups on the propargyl carbon.
• 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.
• 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。