1-(2-ethynyl-2-methyloxirane)methanol tert-butyldimethylsilyl ether | 197307-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-ethynyl-2-methyloxirane)methanol tert-butyldimethylsilyl ether
• 英文别名: Tert-butyl-[(3-ethynyl-3-methyloxiran-2-yl)methoxy]-dimethylsilane
• CAS: 197307-27-0
• 化学式: C₁₂H₂₂O₂Si
• 分子量: 226.391
• InChiKey: XZPKWJFCZOHCDB-UHFFFAOYSA-N

物化性质

• 沸点：
  246.9±35.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-ethynyl-2-methyloxirane)methanol tert-butyldimethylsilyl ether 在 四(甲基苯基膦)钯 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、2.07 MPa 条件下， 反应 2.75h， 生成 methyl (3-methylfuran-2-yl)acetate
  参考文献：
  名称：

  Carbonylation of Alkynyl Epoxides:  Synthesis of 5-Hydroxy-2,3-dienoate Esters and 2,3-Dihydrofuran-3-ol Derivatives

  摘要：

  The carbonylation of alkynyl oxiranes catalyzed by (MePh2)(4)Pd in the presence of 20 atm of carbon monoxide in methanol gives methyl 5-hydroxy-2,3-pentadienoates in good yields. When the reaction is performed on alkynyl oxiranemethanol derivatives, 4,5-dihydrofuran-3-ol derivatives are obtained stereoselectively. These products arise from the spontaneous cyclization of a dihydroxyallenyl ester intermediate.

  DOI：

  10.1021/jo971303n
• 作为产物：
  描述：

  (E)-3-甲基戊-2-烯-4-炔-1-醇 生成 1-(2-ethynyl-2-methyloxirane)methanol tert-butyldimethylsilyl ether
  参考文献：
  名称：

  Carbonylation of Alkynyl Epoxides:  Synthesis of 5-Hydroxy-2,3-dienoate Esters and 2,3-Dihydrofuran-3-ol Derivatives

  摘要：

  The carbonylation of alkynyl oxiranes catalyzed by (MePh2)(4)Pd in the presence of 20 atm of carbon monoxide in methanol gives methyl 5-hydroxy-2,3-pentadienoates in good yields. When the reaction is performed on alkynyl oxiranemethanol derivatives, 4,5-dihydrofuran-3-ol derivatives are obtained stereoselectively. These products arise from the spontaneous cyclization of a dihydroxyallenyl ester intermediate.

  DOI：

  10.1021/jo971303n

文献信息

• Sustainable Micellar Gold Catalysis - Poly(2-oxazolines) as Versatile Amphiphiles
  作者：Linda Lempke、Andrea Ernst、Fabian Kahl、Ralf Weberskirch、Norbert Krause

  DOI：10.1002/adsc.201600139

  日期：2016.4.28

  the gold‐catalyzed allene cycloisomerizations under aqueous micellar conditions is described. The polymers were prepared by ring‐opening cationic polymerization based on poly(2‐methyl‐2‐oxazoline) as hydrophilic segment and different hydrocarbon‐ or fluorocarbon‐based hydrophobic segments. The catalytic activity in the gold‐catalyzed allene cyclization is strongly dependent on the type of gold precursor

  描述了五种聚合物两亲物在水性胶束条件下在金催化的丙二烯环异构化中的应用。这些聚合物是通过以聚（2-甲基-2-恶唑啉）为亲水链段和不同的基于烃或碳氟化合物的疏水链段通过阳离子聚合开环阳离子而制备的。金催化的异戊烯环化反应中的催化活性在很大程度上取决于金前驱体的类型，本体水介质中的盐浓度以及聚合两亲物的浓度。用2 mol％的溴化金（III），1 mM的两亲物和5 M的氯化钠可获得最佳结果，不同杂环产品的收率超过80％。该催化剂体系也适用于炔二醇的脱水环化成呋喃。而且，
• Combined Rhodium/Gold Catalysis: From Propargyloxiranes to 2,5-Dihydrofurans in One Pot
  作者：Özge Aksın-Artok、Norbert Krause

  DOI：10.1002/adsc.201000903

  日期：2011.2.11

  efficient one-pot synthesis of 2,5-dihydrofurans from propargyloxiranes and arylboronic acids takes advantage of sequential rhodium-gold catalysis. The transformation proceeds with center-to-axis-to-center chirality transfer and tolerates a wide variety of electron-accepting or electron-withdrawing substituents at the arylboronic acid, as well as cyclic or acyclic propargyloxiranes.

  由炔丙基环氧乙烷和芳基硼酸进行的新的高效一锅法合成2,5-二氢呋喃利用了顺序的铑-金催化作用。该转变通过中心到中心到中心的手性转移而进行，并且在芳基硼酸以及环状或无环的炔丙基环氧乙烷上容许各种各样的电子接受或吸电子取代基。
• Marshall James A., DuBay William J., J. Org. Chem., 58 (1993) N 12, S 3435-3443
  作者：Marshall James A., DuBay William J.

  DOI：——

  日期：——