7-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hept-2-yn-1-one | 192188-42-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hept-2-yn-1-one
• 英文别名: 7-[Tert-butyl(dimethyl)silyl]oxy-1-phenylhept-2-yn-1-one
• CAS: 192188-42-4
• 化学式: C₁₉H₂₈O₂Si
• 分子量: 316.516
• InChiKey: OEUGBTKGELRZSA-UHFFFAOYSA-N

物化性质

• 沸点：
  384.1±44.0 °C(Predicted)
• 密度：
  0.964±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hept-2-yn-1-one 在 四丁基氟化铵 、 溶剂黄146 、 copper(ll) bromide 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  催化分子内Stetter反应对映体选择性形成四元立体中心

  摘要：

  使用催化的分子内Stetter反应已经完成了四元立体中心的不对称形成。各种束缚的醛和Michael受体以优异的收率和对映选择性被环化。

  DOI：

  10.1016/j.tet.2006.06.042
• 作为产物：
  描述：

  N-甲基-N-甲基苯甲酰胺 、 6-(叔-丁基二甲基硅烷基氧基)-1-己炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以84%的产率得到7-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hept-2-yn-1-one
  参考文献：
  名称：

  Highly Stereoselective Addition of Stannylcuprates to Alkynones

  摘要：

  The addition of stannylcuprate reagents such as (Bu3Sn)(PhS)CuLi to alkynones has been found to proceed in high yield and with excellent stereoselectivity for the Z isomer of the product (>95%). The behavior of the stannylcuprates is thus very different from that of their "carbocuprate" counterparts such as Me2CuLi or Me2Cu(CN)Li-2 which are nonstereoselective. Furthermore, in contrast to the reactions of (R3Sn)(PhS)CuLi with the corresponding alkynoates, the presence of a proton source in the reaction medium has no effect on the stereos electivity of the reaction of alkynones.

  DOI：

  10.1021/jo0259008

文献信息

• Direct alkynyl group transfer from silicon to copper: New preparation method of alkynylcopper (I) reagents
  作者：Hajime Ito、Kikuo Arimoto、Hiro-omi Sensul、Akira Hosomi

  DOI：10.1016/s0040-4039(97)00794-6

  日期：1997.6

  A first observation of the direct alkynyl group transfer from silicon to copper is reported. The silicon group of alkynylsilanes was smoothly replaced by copper (I) chloride in DMI to give the corresponding copper (I) acetylides. This transformation was applied to the synthesis of alkynyl ketones catalyzed by CuCl. (C) 1997 Elsevier Science Ltd.
• Highly Stereoselective Addition of Stannylcuprates to Alkynones
  作者：Thomas E. Nielsen、Maria A. Cubillo de Dios、David Tanner

  DOI：10.1021/jo0259008

  日期：2002.10.1

  The addition of stannylcuprate reagents such as (Bu3Sn)(PhS)CuLi to alkynones has been found to proceed in high yield and with excellent stereoselectivity for the Z isomer of the product (>95%). The behavior of the stannylcuprates is thus very different from that of their "carbocuprate" counterparts such as Me2CuLi or Me2Cu(CN)Li-2 which are nonstereoselective. Furthermore, in contrast to the reactions of (R3Sn)(PhS)CuLi with the corresponding alkynoates, the presence of a proton source in the reaction medium has no effect on the stereos electivity of the reaction of alkynones.
• Enantioselective formation of quaternary stereocenters using the catalytic intramolecular Stetter reaction
  作者：Jennifer L. Moore、Mark S. Kerr、Tomislav Rovis

  DOI：10.1016/j.tet.2006.06.042

  日期：2006.12

  Asymmetric formation of quaternary stereocenters has been accomplished using the catalytic intramolecular Stetter reaction. A variety of tethered aldehydes and Michael acceptors are cyclized in excellent yields and enantioselectivities.

  使用催化的分子内Stetter反应已经完成了四元立体中心的不对称形成。各种束缚的醛和Michael受体以优异的收率和对映选择性被环化。