[2-[Tert-butyl(dimethyl)silyl]-4-trimethylsilylfuran-3-yl]methanol | 117657-88-2

• 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
• 英文名称: [2-[Tert-butyl(dimethyl)silyl]-4-trimethylsilylfuran-3-yl]methanol
• CAS: 117657-88-2
• 化学式: C₁₄H₂₈O₂Si₂
• 分子量: 284.546
• InChiKey: OHFZJVZJPCTTPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三甲基氯硅烷 、 3-呋喃甲醇,2-[(1,1-二甲基乙基)二甲基甲硅烷基]- 在 正丁基锂 、 lithium chloride 作用下， 生成 [2-[Tert-butyl(dimethyl)silyl]-4-trimethylsilylfuran-3-yl]methanol
  参考文献：
  名称：

  4-硫代-2-（叔丁基二甲基甲硅烷基）-3-（羟甲基）呋喃的区域特异性形成和反应：一种3,4-二取代呋喃的方法。

  摘要：

  通过用2.2当量的正丁基锂（DME / 0°C /在15分钟内）被各种亲电试剂捕获，去甲硅烷基化后可产生3,4-二取代的呋喃，产率中等至中等。

  DOI：

  10.1016/s0040-4039(00)80267-1

文献信息

• The regiospecific formation and reactions of 4-lithio-2-(t-butyldimethylsilyl)- 3-(hydroxymethyl)furan: An approach to 3,4-disubstituted furans.
  作者：Edward J. Bures、Brian A. Keay

  DOI：10.1016/s0040-4039(00)80267-1

  日期：1988.1

  4-Lithio-2-(t-butyldimethylsilyl)-3-(hydroxymethyl)furan, generated by treating 2-(t-butyldimethylsilyl)-3-(hydroxymethyl)furan with 2.2 equivalents of n-butyllithium (DME/0°C/15 min), is trapped by a variety of electrophiles to produce, after desilylation, 3,4-disubstituted furans in good to moderate yields.

  通过用2.2当量的正丁基锂（DME / 0°C /在15分钟内）被各种亲电试剂捕获，去甲硅烷基化后可产生3,4-二取代的呋喃，产率中等至中等。
• BURES, EDWARD J.;KEAY, BRIAN A., TETRAHEDRON LETT., 29,(1988) N 11, 1247-1250
  作者：BURES, EDWARD J.、KEAY, BRIAN A.

  DOI：——

  日期：——
• Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 2.¹ Regioselective Lithiation of 2-Silylated-3-substituted Furan Rings
  作者：Edward Bures、James A. Nieman、Shuyuan Yu、Patrick G. Spinazzé、Jean-Louis J. Bontront、Ian R. Hunt、Arvi Rauk、Brian A. Keay

  DOI：10.1021/jo971098b

  日期：1997.12.1

  A new method for the preparation of 3,4- and 2,5-disubstituted furan rings is described. A variety of 2-silylated-3-(hydroxymethyl)furans and 2-silylated-3-furoic acids lithiate exclusively at C-4 when treated with 2.2 equivs of BuLi. The resulting dianions were quenched with a variety of electrophiles to provide 2-silylated-3-(hydroxymethyl)-substituted furans and 2-silylated-4-substituted 3-furoic acids in good to excellent yields. Removal of the silyl group (n-Bu4NF) provided a variety of 4-substituted-3-(hydroxymethyl)furans and methyl 4-substituted-3-furoates, respectively. The latter esters were prepared due to difficulties encountered in isolating 4-substituted-3-furoic acids. The site of lithiation was altered by protecting the 3-hydroxyl group with a triethylsilane. Lithiation of 2-silylated-3-(((triethylsilyl)oxy)methyl)furan with 1.2 equivs of BuLi followed by the addition of electrophiles provided 2-silylated-3-(((triethylsilyl)oxy)methyl)-5-substituted furan rings. Subsequent removal of both silyl groups provided 2,4-disubstituted furan rings in moderate to good yields. A rationale is provided to explain why protection of the hydroxyl group at C-3 leads to a change in lithiation from the C-4 to the C-5 position of the furan ring. In addition, an explanation for the observed effect of adding HMPA or LiCl to the solution during the lithiation of 2-(tert-butyldimethylsilyl)-3-(hydroxymethyl)furan is provided.