2-methyl-5-triethylsilyl-3-furaldehyde | 141293-82-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-5-triethylsilyl-3-furaldehyde
• 英文别名: 5-methyl-2-triethylsilyl-4-furaldehyde；5-Methy-2-triethylsilyl-4-furaldehyde；2-methyl-5-triethylsilylfuran-3-carbaldehyde
• CAS: 141293-82-5
• 化学式: C₁₂H₂₀O₂Si
• 分子量: 224.375
• InChiKey: VZPXDFPLYCSOPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  Lithium aluminium hydride 、 2-methyl-5-triethylsilyl-3-furaldehyde 在 氩 、 盐酸 、 乙醚 、 水 、 Brine 、 magnesium sulfate 、 silica 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 5-Methyl-2-triethylsilyl-furan-4-ylmethanol
  参考文献：
  名称：

  Pharmaceutical compositions and method for administering 3 and

  摘要：

  3和4取代的2（5H）-呋喃酮化合物影响哺乳动物，包括人类的骨生成和骨吸收的平衡。活性化合物以有效剂量给予哺乳动物，包括人类，每千克体重每天范围在0.05至100毫克之间，以影响骨生成和骨吸收的平衡，特别是用于治疗骨质疏松症。

  公开号：

  US05541221A1
• 作为产物：
  描述：

  3-糠醛 、 三乙基氯硅烷 、 碘甲烷 生成 5-Triethylsilyl-3-furaldehyde 、 2-methyl-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

文献信息

• Intermediates and processes for preparing 4-substituted 2-5(H)-furanones
  申请人：Allergan, Inc.

  公开号：US05082954A1

  公开（公告）日：1992-01-21

  Anti-inflammatory 4-substituted 2-furanones are made from intermediates having the formulas: ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 independently are n-alkyl of 1 to 6 carbons, or branched chain alkyl of 1 to 6 carbons; X is H, OH, NH.sub.2, I or Br; R.sub.4 is H, alkyl of 1-20 carbons, phenyl[C.sub.1 -C.sub.20 alkyl], naphthyl[C.sub.1 -C.sub.20 alkyl], 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 or CH.sub.2 --COOR.sub.5, and R.sub.5 is alkyl of 1 to 6 carbons, with the proviso that when X is hydrogen then R.sub.4 is selected from the group consisting of CH.sub.2 OH, CH.sub.2 NH.sub.2, CH.sub.2 CH.sub.2 OH, CH.sub.2 --CHO, or CH.sub.2 --COOR.sub.5 ; ##STR2## in which R.sub.1, R.sub.2 and R.sub.3 independently are n-alkyl of 1 to 6 carbons, or branched chain alkyl or 1 to 6 carbons, and R.sub.5 is alkyl or 1 to 6 carbons; ##STR3## in which R.sub.1, R.sub.2 and R.sub.3 independently are n-alkyl of 1 to 6 carbons, or branched chain alkyl of 1 to 6 carbons, and R.sub.6 is phenyl, or alkyl of 1 to 6 carbons, and ##STR4## in which R.sub.1, R.sub.2 and R.sub.3 independently are n-alkyl of 1 to 6 carbons, or branched chain alkyl of 1 to 6 carbons.

  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。
• Intermediates for preparing 4-substituted 2-5(H)-furanones as
  申请人：Allergan, Inc.

  公开号：US05171863A1

  公开（公告）日：1992-12-15

  Anti-inflammatory 4-substituted 2-furanones are made from intermediates having the formulas: ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 independently are n-alkyl of 1 to 6 carbons, or branched chain alkyl of 1 to 6 carbons; X is H, OH, NH.sub.2, I or Br; R.sub.4 is H, alkyl of 1-20 carbons, phenyl[C.sub.1 -C.sub.20 alkyl], naphthyl[C.sub.1 -C.sub.20 alkyl], 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 or CH.sub.2 --COOR.sub.5, and R.sub.5 is alkyl of 1 to 6 carbons, with the proviso that when X is hydrogen then R.sub.4 is selected from the group consisting of CH.sub.2 OH, CH.sub.2 NH.sub.2, CH.sub.2 CH.sub.2 OH, CH.sub.2 --CHO, or CH.sub.2 --COOR.sub.5 ; ##STR2## in which R.sub.1, R.sub.2 R.sub.3 independently are n-alkyl of 1 to 6 carbons, or branched chain alkyl of 1 to 6 carbons, and R.sub.5 is alkyl of 1 to 6 carbons; ##STR3## in which R.sub.1, R.sub.2 and R.sub.3 independently are n-alkyl of 1 to 6 carbons, or branched chain alkyl of 1 to 6 carbons, and R.sub.6 is phenyl, or alkyl of 1 to 6 carbons, and ##STR4## in which R.sub.1, R.sub.2 and R.sub.3 independently are n-alkyl of 1 to 6 carbons, or branched chain alkyl of 1 to 6 carbons.

  抗炎4-取代2-呋喃酮是由中间体制备而成，其化学式如下：##STR1## 其中，R.sub.1、R.sub.2和R.sub.3独立地是1到6个碳的n-烷基，或者是1到6个碳的支链烷基；X是H、OH、NH.sub.2、I或Br；R.sub.4是H、1-20个碳的烷基、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，其中R.sub.5是1到6个碳的烷基，但是当X是氢时，R.sub.4的选择范围包括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；##STR2## 其中，R.sub.1、R.sub.2和R.sub.3独立地是1到6个碳的n-烷基，或者是1到6个碳的支链烷基，而R.sub.5是1到6个碳的烷基；##STR3## 其中，R.sub.1、R.sub.2和R.sub.3独立地是1到6个碳的n-烷基，或者是1到6个碳的支链烷基，而R.sub.6是苯基或1到6个碳的烷基；##STR4## 其中，R.sub.1、R.sub.2和R.sub.3独立地是1到6个碳的n-烷基，或者是1到6个碳的支链烷基。
• 2- and 5-alkyl and phenyl substituted 4-(1-hydroxy, 1-acyloxy or
  申请人：Allergan, Inc.

  公开号：US05183906A1

  公开（公告）日：1993-02-02

  Novel anti-inflammatory furanone compounds have the following formula ##STR1## where R.sub.1 independently is H, phenyl, C.sub.1 -C.sub.6 alkyl substituted phenyl, halogen substituted phenyl, or alkyl of 1 to 6 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 either to the 3 or 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 olephinic bonds, PO(OH).sub.2, PO(OH)OR.sub.2, PO(OH)R.sub.2, PO(OR.sub.2).sub.2, where R.sub.2 is independently alkyl of 1 to 20 carbons, phenyl, or halogen substituted phenyl or C.sub.1 -C.sub.6 alkyl substituted phenyl, further Y.sub.1 is CO--R.sub.3, CO--OR.sub.3, CONHR.sub.3, SO.sub.2 R.sub.3, SO.sub.2 NHR.sub.3, (CH.sub.2).sub.p --O--R.sub.3, or (CH.sub.2).sub.p --O--(CH.sub.2).sub.m --O--R.sub.3, where p, and m, are integers and are independently 1 to 20 and R.sub.3 is H, C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl containing one or more olephinic 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--R.sub.3, CO--OR.sub.3, and CONHR.sub.3 then R.sub.3 is not hydrogen; Y.sub.2 is H, an alkyl group of 1 to 25 carbons, phenyl, naphthyl, phenyl (C.sub.1 -C.sub.20)alkyl-, naphthyl (C.sub.1 -C.sub.20)alkyl-, halogen substituted phenyl, C.sub.1 -C.sub.6 alkyl substituted phenyl, halogen substituted naphthyl, C.sub.1 -C.sub.6 substituted naphthyl; Y.sub.3 is H, alkyl of 1 to 20 carbons, CO--R.sub.4, CO--O--R.sub.4, CO--NH--R.sub.4, PO(OR.sub.4).sub.2 or PO(OR.sub.4)R.sub.4, where R.sub.4 independently is H, alkyl of 1 to 20 carbons, phenyl, or halogen substituted phenyl or C.sub.1 -C.sub.6 alkyl substituted phenyl.

  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。
• 2-trialkylsilyl-3-furaldehydes
  申请人：Allergan, Inc.

  公开号：US05322953A1

  公开（公告）日：1994-06-21

  Anti-inflammatory 4-substituted 2-furanones are made from intermediates having the formula ##STR1## where R.sub.1, R.sub.2 and R.sub.3 independently are n-or branched chain alkyl of 1 to 6 carbons. These compounds can be used as intermediates to produce 4-substituted 2-furanones which are anti-inflammatory agents.

  抗炎4-取代的2-呋喃酮是由具有以下公式的中间体制备的：##STR1## 其中R.sub.1、R.sub.2和R.sub.3分别是1至6个碳原子的n-或支链烷基。这些化合物可用作中间体，以生产具有抗炎作用的4-取代的2-呋喃酮。