triethylsilyl propynoic acid ethyl ester | 500297-70-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: triethylsilyl propynoic acid ethyl ester
• 英文别名: ethyl 3-(triethylsilyl)propiolate；Ethyl 3-triethylsilylprop-2-ynoate
• CAS: 500297-70-1
• 化学式: C₁₁H₂₀O₂Si
• 分子量: 212.364
• InChiKey: NZIORYRAWDIJJO-UHFFFAOYSA-N

物化性质

• 沸点：
  244.8±9.0 °C(Predicted)
• 密度：
  0.912±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  triethylsilyl propynoic acid ethyl ester 在 四(三苯基膦)钯 potassium carbonate 、 lithium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 16.5h， 生成 2-acetoxy-1,1-diphenyl-4-triethylsilyl-but-1-en-3-yne
  参考文献：
  名称：

  Synthesis and Derivatization of Ethynyl α,α-Dibromomethyl Ketones:  Formation of Highly Functionalized Vinyl Triflates

  摘要：

  [GRAPHICS]We describe the synthesis of alpha,alpha-dibromomethyl ynones (8) and their subsequent derivatization to vinyl acetates (10). These vinyl acetates feature a 1,1-dibromo-olefin moiety, which is readily exploited in palladium-catalyzed Sonogashira, Stille, and Suzuki cross-coupling reactions with alkynes, stannanes, and boronic acids, respectively. A novel one-pot process then directly converts the resulting vinyl acetates 11-13 to the vinyl triflate derivatives 14a-j.

  DOI：

  10.1021/ol027267i
• 作为产物：
  描述：

  三乙基矽乙炔 、 氯甲酸乙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以71%的产率得到triethylsilyl propynoic acid ethyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of (E)-2-En-4-ynoic Acids with Ynolates: Catalytic Conversion to Tetronic Acids and 2-Pyrones

  摘要：

  A highly torquoselective olefination of alkynoates to provide functionalized tetrasubstituted olefins, (E)-2-en-4-ynoic acids, is described. Addition of Bronsted acids dramatically switched the mode of the Ag(l)-catalyzed cyclization of the resulting enyne carboxylic acids to give either tetronic acids or 2-pyrones.

  DOI：

  10.1021/ol902086t

文献信息

• Highly Regioselective and <i>E</i>/<i>Z</i>-Selective Hydroalkylation of Ynone, Ynoate, and Ynamide via Photoredox Mediated Ni/Ir Dual Catalysis
  作者：Su Yong Go、Geun Seok Lee、Soon Hyeok Hong

  DOI：10.1021/acs.orglett.8b02017

  日期：2018.8.3

  Exclusively α- and highly E/Z-selective hydroalkylation of ynone, ynoate, and ynamide was achieved via photoredox mediated Ni/Ir dual catalysis with high atom and step economy, producing trisubstituted enones, which are versatile synthetic building blocks. The developed reaction selectively delivered the α/Z isomer, which is complementary to the previously reported β-alkylation processes. The trisubstituted

  通过光氧化还原介导的Ni / Ir双重催化，高原子和步长经济性，实现了对酮，炔酸酯和炔酰胺的α-和高度E / Z选择性加氢烷基化反应，产生了三取代的烯酮，这是通用的合成原料。发达的反应选择性地递送了α/ Z异构体，这与先前报道的β-烷基化过程是互补的。三取代的烯酮可以通过后官能化转化为更有价值的化合物。
• Stereoselective Synthesis of (<i>E</i>)-2-En-4-ynoic Acids with Ynolates: Catalytic Conversion to Tetronic Acids and 2-Pyrones
  作者：Takashi Yoshikawa、Mitsuru Shindo

  DOI：10.1021/ol902086t

  日期：2009.12.3

  A highly torquoselective olefination of alkynoates to provide functionalized tetrasubstituted olefins, (E)-2-en-4-ynoic acids, is described. Addition of Bronsted acids dramatically switched the mode of the Ag(l)-catalyzed cyclization of the resulting enyne carboxylic acids to give either tetronic acids or 2-pyrones.
• Synthesis and Derivatization of Ethynyl α,α-Dibromomethyl Ketones:  Formation of Highly Functionalized Vinyl Triflates
  作者：Trent Rankin、Rik R. Tykwinski

  DOI：10.1021/ol027267i

  日期：2003.1.1

  [GRAPHICS]We describe the synthesis of alpha,alpha-dibromomethyl ynones (8) and their subsequent derivatization to vinyl acetates (10). These vinyl acetates feature a 1,1-dibromo-olefin moiety, which is readily exploited in palladium-catalyzed Sonogashira, Stille, and Suzuki cross-coupling reactions with alkynes, stannanes, and boronic acids, respectively. A novel one-pot process then directly converts the resulting vinyl acetates 11-13 to the vinyl triflate derivatives 14a-j.