2-butyl-5-triethylsilyl-3-furaldehyde | 141319-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-butyl-5-triethylsilyl-3-furaldehyde
• 英文别名: 5-butyl-2-triethylsilyl-4-furaldehyde；2-butyl-5-triethylsilylfuran-3-carbaldehyde
• CAS: 141319-42-8
• 化学式: C₁₅H₂₆O₂Si
• 分子量: 266.456
• InChiKey: PNCJZSCXVQTLPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  magnesium,dodecane,bromide 、 异氰酸苯酯 、 2-butyl-5-triethylsilyl-3-furaldehyde 以 四氢呋喃 为溶剂， 生成 5-Butyl-4-(1-phenylcarbamoyloxy)tridecyl-2-triethylsilylfuran
  参考文献：
  名称：

  Intermediates and processes for preparing 4-substituted 2-5(H)-furanones

  摘要：

  抗炎症的4-取代的2-呋喃酮是由具有以下结构的中间体制备的：##STR1## 其中R.sub.1，R.sub.2和R.sub.3独立地是1到6个碳原子的n-烷基，或者1到6个碳原子的支链烷基；X是H，OH，NH.sub.2，I或Br；R.sub.4是H，1-20个碳原子的烷基，苯基[C.sub.1-C.sub.20烷基]，萘基[C.sub.1-C.sub.20烷基]，CH.sub.2 OH，CH.sub.2 NH.sub.2，CH.sub.2 CH.sub.2 OH，CH.sub.2 --CHO，CH.sub.2 --COOH或CH.sub.2 --COOR.sub.5，而R.sub.5是1到6个碳原子的烷基，但当X为氢时，R.sub.4从CH.sub.2 OH，CH.sub.2 NH.sub.2，CH.sub.2 CH.sub.2 OH，CH.sub.2 --CHO或CH.sub.2 --COOR.sub.5的组中选择；##STR2## 其中R.sub.1，R.sub.2和R.sub.3独立地是1到6个碳原子的n-烷基，或者1到6个碳原子的支链烷基，而R.sub.5是1到6个碳原子的烷基；##STR3## 其中R.sub.1，R.sub.2和R.sub.3独立地是1到6个碳原子的n-烷基，或者1到6个碳原子的支链烷基，而R.sub.6是苯基，或者1到6个碳原子的烷基，以及##STR4## 其中R.sub.1，R.sub.2和R.sub.3独立地是1到6个碳原子的n-烷基，或者1到6个碳原子的支链烷基。

  公开号：

  US05082954A1
• 作为产物：
  描述：

  1-碘丁烷 、 2-triethylsilyl-4-furaldehyde semicarbazone 生成 2-butyl-5-triethylsilyl-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
• 作为试剂：
  描述：

  2-methyl-5-trimethylsilyl-3-furaldehyde 、 2-(trimethylsilyl)-4-furaldehyde 、 碘甲烷 、 5-Triethylsilyl-3-furaldehyde 、 1-碘丁烷 在 2-butyl-5-triethylsilyl-3-furaldehyde 作用下， 以respectively, gives 5-butyl-2-triethylsilyl-4-furaldehyde (Compound 41)的产率得到2-butyl-5-triethylsilyl-3-furaldehyde
  参考文献：
  名称：

  2- and 5-alkyl and phenyl substituted 4-(1-hydroxy, 1-acyloxy or

  摘要：

  新型抗炎症呋喃酮类化合物的化学式如下：##STR1## 其中，R.sub.1独立地为H，苯基，C.sub.1-C.sub.6烷基取代的苯基，卤素取代的苯基，或1至6个碳的烷基，n为整数，取值为1或2，当n为1时，R.sub.1基团连接到2-呋喃酮的3或5位，当n为2时，R.sub.1连接到3和5位，但n为1时，R.sub.1不为H；Y.sub.1为H，1至20个碳的烷基，苯基C.sub.1-C.sub.20烷基，C.sub.1-C.sub.20烯基，含有一个或多个烯丙基键的PO(OH).sub.2，PO(OH)OR.sub.2，PO(OH)R.sub.2，PO(OR.sub.2).sub.2，其中R.sub.2独立地为1至20个碳的烷基，苯基，或卤素取代的苯基或C.sub.1-C.sub.6烷基取代的苯基，此外，当Y.sub.1为CO--R.sub.3，CO--OR.sub.3和CONHR.sub.3时，R.sub.3不为氢；Y.sub.2为H，1至25个碳的烷基，苯基，萘基，苯基(C.sub.1-C.sub.20)烷基，萘基(C.sub.1-C.sub.20)烷基，卤素取代的苯基，C.sub.1-C.sub.6烷基取代的苯基，卤素取代的萘基，C.sub.1-C.sub.6取代的萘基；Y.sub.3为H，1至20个碳的烷基，CO--R.sub.4，CO--O--R.sub.4，CO--NH--R.sub.4，PO(OR.sub.4).sub.2或PO(OR.sub.4)R.sub.4，其中R.sub.4独立地为H，1至20个碳的烷基，苯基，或卤素取代的苯基或C.sub.1-C.sub.6烷基取代的苯基。

  公开号：

  US05183906A1

文献信息

• Pharmaceutical compositions and method for administering 3 and
  申请人：Allergan, Inc.

  公开号：US05387606A1

  公开（公告）日：1995-02-07

  3 and 4-substituted 2(5H)-furanone compounds influence the balance between bone production and bone resorption in mammals, including humans. The active compounds are administered to mammals, including humans, in an effective dose which ranges between 0.05 to 100 mg per kilogram, body weight, per day, for the purpose of influencing the balance between bone production and bone resorption, and particularly for treating osteoporosis.

  3和4取代的2（5H）-呋喃酮化合物影响哺乳动物，包括人类的骨生产和骨吸收平衡。活性化合物以有效剂量给哺乳动物，包括人类，每日剂量范围为0.05至100毫克/千克体重，以影响骨生产和骨吸收的平衡，特别是用于治疗骨质疏松症。