4-phenyl-5-trimethylsilyl-3-furancarboxaldehyde | 141293-91-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-phenyl-5-trimethylsilyl-3-furancarboxaldehyde
• 英文别名: 2-trimethylsilyl-3-phenyl-4-furaldehyde；4-Phenyl-5-trimethylsilylfuran-3-carbaldehyde
• CAS: 141293-91-6
• 化学式: C₁₄H₁₆O₂Si
• 分子量: 244.365
• InChiKey: SZOUYHSCSQFOGS-UHFFFAOYSA-N

物化性质

• 沸点：
  324.1±42.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  月桂酰氯 、 rose bengal 、 4-phenyl-5-trimethylsilyl-3-furancarboxaldehyde 在 正丁基锂 、 LiAlH4 、 三乙胺 、 lithium chloride 、 碘甲烷 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 4-Dodecoyloxymethyl-5-hydroxy-5-methyl-3-phenyl-2-furanone
  参考文献：
  名称：

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

  摘要：

  新型抗炎烯酮化合物具有以下式：##STR1## 其中R.sub.1独立地是H，或者由1到9个碳组成的烷基，n是一个整数，其值为1或2，当n为1时，R.sub.1基附加在2-糠酮的5位，当n为2时，R.sub.1附加在3位和5位，但是当n为1时，R.sub.1不是H；Y.sub.1是H，由1到20个碳组成的烷基，苯基C.sub.1-C.sub.20烷基，含有一个或多个烯烃键的C.sub.1-C.sub.20烯基，其中R.sub.3是H，C.sub.1-C.sub.20烷基，含有一个或多个烯烃键的C.sub.1-C.sub.20烯基，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H，由1到25个碳组成的烷基，或苯基。

  公开号：

  US05451686A1
• 作为产物：
  描述：

  三甲基氯硅烷 、 4-phenyl-3-furaldehyde 生成 4-phenyl-5-trimethylsilyl-3-furancarboxaldehyde
  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

文献信息

• 3 and 5 alkyl and phenyl 4-(hydroxy or acyloxy)-alkyl substituted
  申请人：Allergan, Inc.

  公开号：US05451686A1

  公开（公告）日：1995-09-19

  Novel anti-inflammatory furanone compounds have the following formula: ##STR1## where R.sub.1 independently is H, or alkyl of 1 to 9 carbons and n is an integer having the values of 1 or 2, and where when n is 1 the R.sub.1 group is attached to the 5 position of the 2-furanone, when n is 2 then R.sub.1 is attached to both the 3 and 5 positions, with the proviso that when n is 1 then R.sub.1 is not H; Y.sub.1 is H, alkyl of 1 to 20 carbons, phenyl C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl containing one or more olefinic bonds, where R.sub.3 is H, C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl containing one or more olefinic bonds, phenyl, halogen substituted phenyl or C.sub.1 -C.sub.6 alkyl substituted phenyl, with the proviso that when Y.sub.1 is CO--OR.sub.3 or CONHR.sub.3 then R.sub.3 is not hydrogen; Y.sub.2 is H, an alkyl group of 1 to 25 carbons, or phenyl.

  新型抗炎烯酮化合物具有以下式：##STR1## 其中R.sub.1独立地是H，或者由1到9个碳组成的烷基，n是一个整数，其值为1或2，当n为1时，R.sub.1基附加在2-糠酮的5位，当n为2时，R.sub.1附加在3位和5位，但是当n为1时，R.sub.1不是H；Y.sub.1是H，由1到20个碳组成的烷基，苯基C.sub.1-C.sub.20烷基，含有一个或多个烯烃键的C.sub.1-C.sub.20烯基，其中R.sub.3是H，C.sub.1-C.sub.20烷基，含有一个或多个烯烃键的C.sub.1-C.sub.20烯基，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H，由1到25个碳组成的烷基，或苯基。
• A general approach to 5-substitution of 3-furaldehydes
  作者：Gary C. M. Lee、Judy M. Holmes、Dale A. Harcourt、Michael E. Garst

  DOI：10.1021/jo00037a032

  日期：1992.5

  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.