5-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-pent-2-yn-1-one | 476445-29-1

• 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: 5-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-pent-2-yn-1-one
• 英文别名: 2-Pentyn-1-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-phenyl-；5-[tert-butyl(dimethyl)silyl]oxy-1-phenylpent-2-yn-1-one
• CAS: 476445-29-1
• 化学式: C₁₇H₂₄O₂Si
• 分子量: 288.462
• InChiKey: PHLRRLJGCOLHSX-UHFFFAOYSA-N

物化性质

• 沸点：
  348.4±44.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  1,3-丙二硫醇 、 5-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-pent-2-yn-1-one 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以94%的产率得到2-{2-[2-(tert-butyldimethylsilanyloxy)-ethyl]-[1,3]dithian-2-yl}-1-phenyl-ethanone
  参考文献：
  名称：

  二硫醇双键加成到炔丙基羰基体系中以生成受保护的1,3-二羰基化合物

  摘要：

  该工作描述了在甲醇钠存在下，将乙烷和丙烷二硫醇有效地双共轭加成到各种含炔丙基羰基的化合物中。这些反应的产物是可用于各种合成程序的有区别的1，3-二羰基体系。通过明智地使用羟基化的底物，发生串联环化反应，得到四氢吡喃内酯，或者在羟基取代的炔丙基酯的情况下得到内酯。相应的氨基取代的炔丙基醛经双共轭加成串联环化得到哌啶衍生物。

  DOI：

  10.1021/jo052514s
• 作为产物：
  描述：

  4-(叔丁基二甲基硅杂氧基)-1-丁炔 、 苯甲酰氯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以76%的产率得到5-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-pent-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

• An efficient palladium-catalyzed coupling reaction of lithium alkynyltriisopropoxyborates with acid chlorides: a new access to synthesis of conjugated ynones
  作者：Chang Ho Oh、V. Raghava Reddy

  DOI：10.1016/j.tetlet.2004.09.114

  日期：2004.11

  An efficient palladium-catalyzed protocol for the synthesis of ynones from lithium alkynyltriisopropoxyborates with acid chlorides under mild neutral conditions.

  在温和的中性条件下，由炔基三异丙氧基硼酸锂与酰氯合成炔酮的有效钯催化方案。
• Development of β-keto 1,3-dithianes as versatile intermediates for organic synthesis
  作者：Matthew J. Gaunt、Helen F. Sneddon、Peter R. Hewitt、Paolo Orsini、David F. Hook、Steven V. Ley.

  DOI：10.1039/b208982c

  日期：——

  β-Keto 1,3-dithianes can be generated by the double conjugate addition of dithiols to propargylic ketones, esters and aldehydes in excellent yields. As masked 1,3-dicarbonyl systems these substrates can be converted to a range of functionalised oxygen-containing heterocycles that can be used in natural product synthesis.

  β-酮 1,3-二噻烷可以通过二硫醇与炔丙酮、酯和醛的双共轭加成生成，产率极好。作为掩蔽的 1,3-二羰基系统，这些底物可以转化为一系列可用于天然产物合成的官能化含氧杂环。
• Double Conjugate Addition of Dithiols to Propargylic Carbonyl Systems To Generate Protected 1,3-Dicarbonyl Compounds
  作者：Helen F. Sneddon、Alexandra van den Heuvel、Anna K. H. Hirsch、Richard A. Booth、David M. Shaw、Matthew J. Gaunt、Steven V. Ley

  DOI：10.1021/jo052514s

  日期：2006.3.31

  methoxide to a wide variety of propargylic carbonyl containing compounds. The products of these reactions are differentiated, 1,3-dicarbonyl systems useful for various synthesis programs. By judicious use of hydroxylated substrates tandem cyclization occurs to afford tetrahydropyran lactols or, in the case of hydroxy-substituted propargylic esters, lactones. The corresponding amino-substituted propargylic

  该工作描述了在甲醇钠存在下，将乙烷和丙烷二硫醇有效地双共轭加成到各种含炔丙基羰基的化合物中。这些反应的产物是可用于各种合成程序的有区别的1，3-二羰基体系。通过明智地使用羟基化的底物，发生串联环化反应，得到四氢吡喃内酯，或者在羟基取代的炔丙基酯的情况下得到内酯。相应的氨基取代的炔丙基醛经双共轭加成串联环化得到哌啶衍生物。
• 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.