4-(1-Hydroxymethyl)-2-trimethylsilylfuran | 94742-49-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4-(1-Hydroxymethyl)-2-trimethylsilylfuran
• 英文别名: 5-trimethylsilyl-3-hydroxymethylfuran；3-(5-trimethylsilyl)furylmethanol；2-trimethylsilyl-4-furanmethanol；5-trimethylsilyl-3-furylmethanol；2-trimethylsilyl-4-hydroxymethylfuran；4-hydroxymethyl-2-trimethylsilylfuran；(2-Trimethylsilyl-4-furyl)methanol；(5-trimethylsilylfuran-3-yl)methanol
• CAS: 94742-49-1
• 化学式: C₈H₁₄O₂Si
• 分子量: 170.283
• InChiKey: GSMUPTHGSLMVML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  4-(1-Hydroxymethyl)-2-trimethylsilylfuran 以79%的产率得到2-(trimethylsilyl)-4-furaldehyde
  参考文献：
  名称：

  Two syntheses of manoalide via heteroatom-assisted alkyne carbometallation

  摘要：

  Two approaches to the sesterterpenoid phospholipase A(2) inhibitors seco-manoalide (3) and manoalide (1) are described based on carbometallation of propargylic alcohols to generate the functionalised C6-C7 trisubstituted alkene. Both syntheses also deploy the photooxidation of a furan in order to generate a 4-substituted-5-hydroxy-2(5H)-furanone moiety.

  DOI：

  10.1016/s0040-4020(01)85353-9
• 作为产物：
  描述：

  2-(trimethylsilyl)-4-furaldehyde 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 4-(1-Hydroxymethyl)-2-trimethylsilylfuran
  参考文献：
  名称：

  钯催化的 3-芳基氧化吲哚的不对称苄基化反应

  摘要：

  在这里，我们报告了钯催化的不对称苄基烷基化，以 3-芳基羟吲哚作为前手性亲核试剂。与不对称烯丙基烷基化类似地进行，使用手性双膦配体对各种未保护的 3-芳基羟吲哚和苄基甲基碳酸酯以高产率和对映选择性发生不对称苄化。该方法代表在苄基和前手性亲核试剂之间形成新的不对称碳-碳键以生成季中心。

  DOI：

  10.1021/ja1079755

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。
• Anti-inflammatory furanones
  申请人：Allergan, Inc.

  公开号：US05134128A1

  公开（公告）日：1992-07-28

  New 5-hydroxy-2-furanone compounds having anti-inflammatory, immunosuppressive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis.

  新的具有抗炎、免疫抑制和抗增殖活性的5-羟基-2-呋喃酮化合物对治疗牛皮癣和调节钙稳态具有用处。
• Synthetic studies on prehispanolone and 14,15-dihydroprehispanolone
  作者：En Si Wang、Yuen Min Choy、Henry N.C. Wong

  DOI：10.1016/0040-4020(96)00705-3

  日期：1996.9

  Michael addition as a pivotal step, butenolide 5, furans 6 and 7 have been converted to dioxaspiro compounds 8, 9, 10 and 11, whose heterocyclic frameworks constitute important structural units of prehispanolone (2) as well as 14,15-dihydroprehispanolones (3) and (4), respectively. Hispanolone (1) was converted to 2, 3 and 4 by utilizing a similar strategy.

  利用分子内迈克尔加成法作为关键步骤，丁烯内酯5，呋喃6和7已转化为二氧杂螺环化合物8、9、10和11，它们的杂环骨架构成了prehispanolone（2）以及14,15-的重要结构单元。二氢普hi烷酮（3）和（4）。通过使用类似的策略，将史帕诺龙（1）转换为2、3和4。
• Pharmaceutical compositions and method for administering 3 and
  申请人：Allergan, Inc.

  公开号：US05268387A1

  公开（公告）日：1993-12-07

  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，包括人类的骨生成和骨吸收之间的平衡。这些活性化合物以有效剂量（每公斤体重范围在0.05至100毫克之间）被用于哺乳动物，包括人类，旨在影响骨生成和骨吸收之间的平衡，特别用于治疗骨质疏松症。
• 4-(oxygen, sulfur or nitrogen substituted)-methyl
  申请人：Allergan, Inc.

  公开号：US05037811A1

  公开（公告）日：1991-08-06

  Compounds of the formula ##STR1## in which R.sub.1 is H or alkyl of 1 to 20 carbons, CO--R.sub.1.sup.* CO--O--R.sub.1.sup.* CO--NH--R.sub.1.sup.* or PO(OR.sub.1.sup.*).sub.2 or PO(OR.sub.1.sup.*)R.sub.1.sup.* where R.sub.1.sup.* independently is H, alkyl of 1 to 20 carbons, phenyl, or substituted phenyl; X is O, S, SO--, SO.sub.2, NH--, or NR.sub.2 where R.sub.2 is phenyl, substituted phenyl or alkyl of 1 to 20 carbons, and Y is alkyl having at least 6 carbon atoms, arylalkyl, aryl, substituted aryl, substituted arylalkyl, alkenyl containing one or more olephinic bonds and at least 6 carbon atoms, CO--R.sub.3, CO--OR.sub.3, CONHR.sub.3, SO.sub.2 R.sub.3, SO.sub.2 NHR.sub.3 where R.sub.3 is aryl, substituted aryl, substituted arylalkyl, alkyl, alkenyl containing one or more olephinic bonds, further Y is (CH.sub.2).sub.n --O--R.sub.4, or (CH.sub.2).sub.n --O--(CH.sub.2).sub.m --O--R.sub.4, where n, and m, are integers and are independently 1 to 25 and R.sub.4 is phenyl, substituted phenyl or alkyl of one to 20 carbons, still further Y is PO(OH).sub.2, PO(OH)OR.sub.5, PO(OH)R.sub.5 PO(OR.sub.5).sub.2, where R.sub.5 is independently phenyl, substituted phenyl, alkyl or 1 to 20 carbons or R.sub.5 is (CH.sub.2).sub.n --N(R.sub.5.sup.*).sub.3 where R.sub.5.sup.* is alkyl of 1 to 20 carbons, or Y is NH--R.sub.6 where R.sub.6 is phenyl, substituted phenyl or alkyl of at least 6 carbon atoms with the proviso that when X is O, S, then Y is not NH--R.sub.6, and with the further proviso that when X is SO or SO.sub.2 then Y is not SO.sub.2 R.sub.3 or SO.sub.2 NHR.sub.3, are disclosed. The compounds possess anti-inflammatory activity.

  式为##STR1##的化合物，其中R.sub.1为H或含有1至20个碳原子的烷基，CO--R.sub.1.sup.* CO--O--R.sub.1.sup.* CO--NH--R.sub.1.sup.*或PO(OR.sub.1.sup.*).sub.2或PO(OR.sub.1.sup.*)R.sub.1.sup.*，其中R.sub.1.sup.*独立地为H、含有1至20个碳原子的烷基、苯基或取代苯基；X为O、S、SO--、SO.sub.2、NH--或NR.sub.2，其中R.sub.2为苯基、取代苯基或含有1至20个碳原子的烷基，Y为至少含有6个碳原子的烷基、芳基烷基、芳基、取代芳基、取代芳基烷基、含有一个或多个烯烃键且至少含有6个碳原子的烯烃基、CO--R.sub.3、CO--OR.sub.3、CONHR.sub.3、SO.sub.2 R.sub.3、SO.sub.2 NHR.sub.3，其中R.sub.3为芳基、取代芳基、取代芳基烷基、烷基、含有一个或多个烯烃键的烯烃基，进一步Y为(CH.sub.2).sub.n --O--R.sub.4，或(CH.sub.2).sub.n --O--(CH.sub.2).sub.m --O--R.sub.4，其中n和m为整数，独立地为1至25，R.sub.4为苯基、取代苯基或含有1至20个碳原子的烷基，进一步Y为PO(OH).sub.2、PO(OH)OR.sub.5、PO(OH)R.sub.5 PO(OR.sub.5).sub.2，其中R.sub.5独立地为苯基、取代苯基、含有1至20个碳原子的烷基，或R.sub.5为(CH.sub.2).sub.n --N(R.sub.5.sup.*).sub.3，其中R.sub.5.sup.*为含有1至20个碳原子的烷基，或Y为NH--R.sub.6，其中R.sub.6为苯基、取代苯基或至少含有6个碳原子的烷基，但其中X为O、S时，Y不是NH--R.sub.6，且当X为SO或SO.sub.2时，Y不是SO.sub.2 R.sub.3或SO.sub.2 NHR.sub.3，这些化合物具有抗炎活性。