5-(1-Hydroxy-1-methyldecyl)-3-furaldehyde | 130493-26-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(1-Hydroxy-1-methyldecyl)-3-furaldehyde
• 英文别名: 5-(2-hydroxyundecan-2-yl)furan-3-carbaldehyde
• CAS: 130493-26-4
• 化学式: C₁₆H₂₆O₃
• 分子量: 266.381
• InChiKey: XUZFIQYMRVIFGK-UHFFFAOYSA-N

物化性质

• 沸点：
  386.9±27.0 °C(Predicted)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-糠醛 、 2-十一酮 生成 5-(1-Hydroxy-1-methyldecyl)-3-furaldehyde
  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

• Process for preparing 5-substituted-3-furaldehydes
  申请人：Allergan, Inc.

  公开号：US04935530A1

  公开（公告）日：1990-06-19

  A process for preparing 5-substituted-3-furaldehydes which comprises reacting 3-furaldehyde with lithium morpholide, followed by sec-butyl lithium, followed by an electrophile.

  一种制备5-取代-3-呋喃醛的方法，包括将3-呋喃醛与吗啉锂反应，然后加入丁基锂，最后加入亲电试剂。
• US4935530A
  申请人：——

  公开号：US4935530A

  公开（公告）日：1990-06-19
• 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.