2-呋喃二甲基硅烷醇 | 879904-83-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 2-呋喃二甲基硅烷醇
• 中文别名: 2-呋喃二甲基硅烷醇,97；2-呋喃基二甲基硅烷醇
• 英文名称: 2-(hydroxydimethylsilyl)furan
• 英文别名: furan-3-yldimethylsilanol；(2-furyl)dimethylsilanol；dimethyl(2-furyl)silanol；Furan-2-yl-dimethylsilanol；furan-2-yl-hydroxy-dimethylsilane
• CAS: 879904-83-3
• 化学式: C₆H₁₀O₂Si
• mdl: MFCD09266145
• 分子量: 142.23
• InChiKey: AAYDPVXTNSQTRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.29
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-呋喃二甲基硅烷醇 、 2-碘代甲苯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex sodium hydride 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以61%的产率得到2-(2-methylphenyl)furan
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling of Five-Membered Heterocyclic Silanolates

  摘要：

  The preparation of pi-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables: (1) identification of stable, isolable alkali metal silanolates, (2) identification of conditions for preformation and isolation of silanolate salts, (3) judicious choice in the palladium catalyst/ligand combination, and (4) selection of the protecting group on the nitrogen of indole. It was found that the alkali metal silanolates, either isolated or formed in situ, offered a significant rate enhancement and broader substrate scope over the use of silanols activated by Bronsted bases such as NaOt-Bu. In addition, the optimized conditions for the cross-coupling of 2-indolylsilanolates were readily applied to the cross-coupling of 2-pyrrolyl-, 2-furyl-, and 2-thienylsilanolates.

  DOI：

  10.1021/jo7023784
• 作为产物：
  描述：

  (3-furyldimethylsilyl)methanol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 potassium bromide 、 sodium hypochlorite 、 碳酸氢钠 作用下， 以 丙酮 、 水 为溶剂， 反应 1.17h， 以27%的产率得到2-呋喃二甲基硅烷醇
  参考文献：
  名称：

  A Novel Method for Preparing Silanols from Silylmethanols

  摘要：

  各种类型的硅烷甲醇在温和的氧化条件下使用TEMPO（2,2,6,6-四甲基-1-哌啶氧基）转化为其相应的硅醇，收率良好至优异。

  DOI：

  10.1246/cl.2009.532

文献信息

• Palladium-Catalyzed Cross-Coupling Reactions of Heterocyclic Silanolates with Substituted Aryl Iodides and Bromides
  作者：Scott E. Denmark、John D. Baird

  DOI：10.1021/ol053165r

  日期：2006.2.1

  heterocyclic silanols undergo cross-coupling with a variety of aromatic iodides and bromides under mild conditions. In situ deprotonation of the silanols with an equivalent amount of sodium hydride in toluene generates the sodium salt that couples with iodides under the action of Pd(2)(dba)(3).CHCl(3) in good yield at room temperature to 50 degrees C. The aromatic bromides also couple with these salts

  [反应：见正文]在温和条件下，衍生自多种杂环硅烷醇的硅烷醇钠与各种芳族碘化物和溴化物发生交叉偶联。硅烷醇与甲苯中的等量氢化钠进行原位去质子化反应生成的钠盐在Pd（2）（dba）（3）.CHCl（3）的作用下与碘化物偶合，在室温至50的条件下产率很高芳族溴化物在Pd（I）催化剂12的作用下也与这些盐偶联。
• Heteroaryl bismuthines: a novel synthetic concept and metal⋯π heteroarene interactions
  作者：A. M. Preda、W. B. Schneider、M. Rainer、T. Rüffer、D. Schaarschmidt、H. Lang、M. Mehring

  DOI：10.1039/c7dt01437f

  日期：——

  provides the bismuth oxido cluster [Bi4O2OCMe2(2-C4H3S)}8] (2). In contrast, the reaction of Bi(OtBu)3 and Bi[N(SiMe3)2]3 with the silanols HOSiMe2(2-C4H3X) (X = O, S, Se, and NMe), HOSiMe2(2-C4H2S-5-SiMe3) and HOSiMe2(3-C4H3S) leads to the formation of tris(heteroaryl)bismuthines Bi(2-C4H2X-5-R)3 [where X = O, R = H (3); X = S, R = H (4); X = S, R = SiMe3 (5); X = NMe, R = H (6); X = Se, R = H (7)] and

  通过三个当量的反应形成醇盐Bi [OCMe 2（2-C 4 H 3 S）] 3（1）。用Bi（O t Bu）3制备醇HOCMe 2（2-C 4 H 3 S），然后水解得到铋氧化簇[Bi 4 O 2 OCMe 2（2-C 4 H 3 S）} 8 ] （2）。相反，Bi（O t Bu）3和Bi [N（SiMe 3）2 ] 3的反应与硅烷醇HOSiMe 2（2-C 4 H 3 X）（X = O，S，Se和NMe），HOSiMe 2（2-C 4 H 2 S-5-SiMe 3）和HOS​​iMe 2（3-C 4 H 3 S）导致形成三（杂芳基）双突变蛋白Bi（2-C 4 H 2 X-5-R）3 [其中X = O，R = H（3）; X = S，R = H（4）；X = S，R = SiMe 3（5）；X = NMe，R = H（6）; X = Se，R = H（7）]和Bi（3-C 4 H 3 S）3（
• Palladium-Catalyzed Cross-Coupling of Five-Membered Heterocyclic Silanolates
  作者：Scott E. Denmark、John D. Baird、Christopher S. Regens

  DOI：10.1021/jo7023784

  日期：2008.2.1

  The preparation of pi-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables: (1) identification of stable, isolable alkali metal silanolates, (2) identification of conditions for preformation and isolation of silanolate salts, (3) judicious choice in the palladium catalyst/ligand combination, and (4) selection of the protecting group on the nitrogen of indole. It was found that the alkali metal silanolates, either isolated or formed in situ, offered a significant rate enhancement and broader substrate scope over the use of silanols activated by Bronsted bases such as NaOt-Bu. In addition, the optimized conditions for the cross-coupling of 2-indolylsilanolates were readily applied to the cross-coupling of 2-pyrrolyl-, 2-furyl-, and 2-thienylsilanolates.
• A Novel Method for Preparing Silanols from Silylmethanols
  作者：Daisuke Takeda、Ryo Oyama、Shozo Yamada

  DOI：10.1246/cl.2009.532

  日期：2009.6.5

  Various types of silylmethanols were converted into their corresponding silanols in good to excellent yield under mild oxidation conditions using TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxyl).

  各种类型的硅烷甲醇在温和的氧化条件下使用TEMPO（2,2,6,6-四甲基-1-哌啶氧基）转化为其相应的硅醇，收率良好至优异。