tert-butyl-[5-deuterio-3-(triethylsilyloxymethyl)furan-2-yl]-dimethylsilane | 158360-04-4

• 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: tert-butyl-[5-deuterio-3-(triethylsilyloxymethyl)furan-2-yl]-dimethylsilane
• CAS: 158360-04-4
• 化学式: C₁₇H₃₄O₂Si₂
• 分子量: 327.619
• InChiKey: OKMLQEKIVQSXLE-YSOHJTORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  22.37
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyl-[5-deuterio-3-(triethylsilyloxymethyl)furan-2-yl]-dimethylsilane 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 1.0h， 以77%的产率得到(5-deuteriofuran-3-yl)methanol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo971098b
• 作为产物：
  描述：

  2-(tert-Butyl-dimethyl-silanyl)-3-triethylsilanyloxymethyl-furan 在 正丁基锂 、 氘代甲醇-d 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以95%的产率得到tert-butyl-[5-deuterio-3-(triethylsilyloxymethyl)furan-2-yl]-dimethylsilane
  参考文献：
  名称：

  一种简便的2,4-二取代呋喃制剂

  摘要：

  用1.3当量处理2-（叔丁基二甲基甲硅烷基）-3-（三乙基甲硅烷基氧甲基）呋喃。取正丁基锂（THF，-40°，3h），然后加入各种亲电试剂，得到2,3,5-三取代的呋喃，用四正丁基氟化铵处理后得到2,4-二取代的呋喃中等至极高的产量。

  DOI：

  10.1016/s0040-4039(00)73493-9

文献信息

• Nieman James A., Keay Brian A., Tetrahedron Lett, 35 (1994) N 30, S 5335-5338
  作者：Nieman James A., Keay Brian A.

  DOI：——

  日期：——