(2E)-2-[[4-(dimethylamino)phenyl]methylidene]-1,1-diphenyl-4-trimethylsilylbut-3-yn-1-ol | 943034-07-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E)-2-[[4-(dimethylamino)phenyl]methylidene]-1,1-diphenyl-4-trimethylsilylbut-3-yn-1-ol
• CAS: 943034-07-9
• 化学式: C₂₈H₃₁NOSi
• 分子量: 425.646
• InChiKey: MFMIGJPWHLBLEB-XTCLZLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-2-[[4-(dimethylamino)phenyl]methylidene]-1,1-diphenyl-4-trimethylsilylbut-3-yn-1-ol 、 4-碘氰基苯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium tert-butylate 作用下， 以 水 、 甲苯 、 二甲基亚砜 为溶剂， 反应 7.0h， 以38%的产率得到4-[(4E)-4-[[4-(dimethylamino)phenyl]methylidene]-5,5-diphenylfuran-2-yl]benzonitrile
  参考文献：
  名称：

  Regio- and Stereoselective Cross-Coupling of tert-Propargyl Alcohols with Bis(trimethylsilyl)acetylene and Its Utilization in Constructing a Fluorescent Donor−Acceptor System

  摘要：

  1,1-Disubstituted 3-aryl-2-propyn-1-ols undergo regio- and stereoselective cross-coupling on treatment with bis(trimethylsilyl)acetylene in the presence of a rhodium catalyst via cleavage of C(sp)-C(sp(3)) and C(sp)-Si bonds to produce the corresponding 2-hydroxymethyl-(E)-enynes. The subsequent desilylative Sonogashira coupling followed by base-promoted cyclization affords fluorescent dihydrofuran derivatives.

  DOI：

  10.1021/ol070799k
• 作为产物：
  描述：

  1,1-二苯基-2-丙炔-1-醇 在 [(cod)Rh(OH)]2 1,4-双(二苯基膦)丁烷 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 (2E)-2-[[4-(dimethylamino)phenyl]methylidene]-1,1-diphenyl-4-trimethylsilylbut-3-yn-1-ol
  参考文献：
  名称：

  Regio- and Stereoselective Cross-Coupling of tert-Propargyl Alcohols with Bis(trimethylsilyl)acetylene and Its Utilization in Constructing a Fluorescent Donor−Acceptor System

  摘要：

  1,1-Disubstituted 3-aryl-2-propyn-1-ols undergo regio- and stereoselective cross-coupling on treatment with bis(trimethylsilyl)acetylene in the presence of a rhodium catalyst via cleavage of C(sp)-C(sp(3)) and C(sp)-Si bonds to produce the corresponding 2-hydroxymethyl-(E)-enynes. The subsequent desilylative Sonogashira coupling followed by base-promoted cyclization affords fluorescent dihydrofuran derivatives.

  DOI：

  10.1021/ol070799k

文献信息

• Regio- and Stereoselective Cross-Coupling of <i>tert</i>-Propargyl Alcohols with Bis(trimethylsilyl)acetylene and Its Utilization in Constructing a Fluorescent Donor−Acceptor System
  作者：Akinobu Horita、Hayato Tsurugi、Atsushi Funayama、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol070799k

  日期：2007.5.1

  1,1-Disubstituted 3-aryl-2-propyn-1-ols undergo regio- and stereoselective cross-coupling on treatment with bis(trimethylsilyl)acetylene in the presence of a rhodium catalyst via cleavage of C(sp)-C(sp(3)) and C(sp)-Si bonds to produce the corresponding 2-hydroxymethyl-(E)-enynes. The subsequent desilylative Sonogashira coupling followed by base-promoted cyclization affords fluorescent dihydrofuran derivatives.