(2-Methyl-4-phenyl-5-trimethylsilanyl-furan-3-yl)-methanol | 141293-98-3

• 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: (2-Methyl-4-phenyl-5-trimethylsilanyl-furan-3-yl)-methanol
• 英文别名: 5-Trimethylsilyl-4-phenyl-3-hydroxymethyl-2-methylfuran；(2-methyl-4-phenyl-5-trimethylsilylfuran-3-yl)methanol
• CAS: 141293-98-3
• 化学式: C₁₅H₂₀O₂Si
• 分子量: 260.408
• InChiKey: AUSUIRXUJXCAAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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-Methyl-4-phenyl-5-trimethylsilanyl-furan-3-yl)-methanol 、 月桂酰氯 在 5-Trimethylsilyl-4-phenyl-3-dodecoyloxymethyl-2-methylfuran 作用下， 以 三乙胺 为溶剂， 以to yield 5-trimethylsilyl-4-phenyl-3-dodecoyloxymethyl-2-methylfuran (Compound 15)的产率得到5-Trimethylsilyl-4-phenyl-3-dodecoyloxymethyl-2-methylfuran
  参考文献：
  名称：

  3 and 5 alkyl and phenyl 4-(hydroxy or acyloxy)-alkyl substituted

  摘要：

  新型抗炎症呋喃酮化合物的化学式如下：##STR1##其中，R.sub.1独立地是氢或1至9个碳的烷基，n是具有值为1或2的整数，当n为1时，R.sub.1基团附加在2-呋喃酮的5位，当n为2时，R.sub.1附加在3和5位，但是当n为1时，R.sub.1不是氢；Y.sub.1是氢，1至20个碳的烷基，苯基C.sub.1-C.sub.20烷基，具有一个或多个烯丙基键的C.sub.1-C.sub.20烯基烷基，其中R.sub.3是氢，C.sub.1-C.sub.20烷基，具有一个或多个烯丙基键的C.sub.1-C.sub.20烯基烷基，苯基，卤素取代的苯基或C.sub.1-C.sub.6烷基取代的苯基；但是当Y.sub.1是CO--OR.sub.3或CONHR.sub.3时，R.sub.3不是氢；Y.sub.2是氢，1至25个碳的烷基或苯基。

  公开号：

  US05451686A1
• 作为产物：
  描述：

  (4-Phenyl-5-trimethylsilanyl-furan-3-yl)-methanol 、 碘甲烷 生成 (2-Methyl-4-phenyl-5-trimethylsilanyl-furan-3-yl)-methanol
  参考文献：
  名称：

  A general approach to 5-substitution of 3-furaldehydes

  摘要：

  Herein we report the details of the conversion of 3-furaldehyde into 2-substituted 4-furaldehydes and the transformations of 2-substituted 4-furaldehydes and 4-substituted 3-furaldehydes into tri- and tetrasubstituted furans. We have developed a new disubstituted furan synthesis by applying metalation to the direct conversion of 3-substituted furans into 2,4-disubstituted furans. In situ protection of 3-furaldehyde with lithium morpholide followed by metalation at the C-5 position and quenching with several electrophiles affords 2-substituted 4-furaldehydes in 30-70% yield. The electrophiles include chlorosilanes, chlorostannanes, aldehydes, ketones, and primary iodides. This work provides a general route to a previously relatively inaccessible furan substitution pattern and is the first example of selective metalation at the C-5 position of 3-substituted furans. Other bulky a-alkoxy substituents at C-3 direct remote metalation to C-5 of furan. We examined other 3-furaldehyde metalations. The amino alkoxide intermediate derived from lithio N,N,N'-trimethylethylenediamine and 3-furaldehyde, when treated with BuLi and electrophiles, provided a product mixture which included metalation at the C-4 position of 3-furaldehyde. Several approaches to enhance this unusual C-4 metalation were unsuccessful. Using this amino alkoxide-metalation chemistry, 4-alkyl- or 4-phenyl-3-furaldehyde could be substituted at C-2 or C-5 selectively. Finally we converted trisubstituted furans into tetrasubstituted furans with metalation/electrophilic trapping.

  DOI：

  10.1021/jo00037a032