4-(1-hydroxytridecyl)-2-trimethyl-silylfuran | 130163-03-0

• 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-hydroxytridecyl)-2-trimethyl-silylfuran
• 英文别名: 3-(1-hydroxytridecyl)-5-trimethylsilylfuran；1-(5-trimethylsilylfuran-3-yl)tridecan-1-ol
• CAS: 130163-03-0
• 化学式: C₂₀H₃₈O₂Si
• 分子量: 338.606
• InChiKey: CDFIESMXSMSFNC-UHFFFAOYSA-N

物化性质

• 沸点：
  352.0±12.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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-hydroxytridecyl)-2-trimethyl-silylfuran 在 rose bengal 氧气 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 AGN-190383
  参考文献：
  名称：

  Singlet oxygen oxidation of substituted furans to 5-hydroxy-2(5H)-furanone

  摘要：

  The conditions for the regiospecific singlet oxygen oxidation of various 2,4-disubstituted furans 9 to 4-substituted-2 (5H)-furanones 3 are developed. The presence of a C-2 substituent (e.g., trimethylsilyl, tert-butyldimethylsilyl, or tributylstannyl) in 9 is an absolute requirement for the formation of the 4-substituted-5-hydroxy-2(5H)-furanone regioisomer 3. When the C-2 substituent is triethylsilyl (TES) or TBDMS, however, apart from 3, the corresponding 5-trialkylsiloxy derivative 11 is also isolated in a significant amount. These silyl acetals are unexpectedly stable but can be hydrolyzed back to 3 on stirring with dilute acid. The formation of silyl acetals, to our knowledge, has never been reported in the singlet oxygen oxidation of (trialkylsilyl)furan. A plausible mechanism for their formation is proposed. The presence of a catalytic amount of water in the oxidation of 2-(trialkylsilyl)-4-substituted-furans not only eliminates the formation of the silyl acetals but also speeds up the rate of the oxidation process. Moreover, the oxidation can then be carried out at 0-degrees-C instead of at -78-degrees-C. Oxidation of 2-(1-hydroxyalkyl)-4-substituted-furans in the absence of a reducing agent gives little or no sign of 2,5-disubstituted-6-hydroxy-3(2H)-pyranone 23 but instead 26 selectively. Thus, the (1-hydroxy)alkyl group can be utilized as the trialkylsilyl or trialkylstannyl group in dictating the regioselectivity in the singlet oxygen oxidation of substituted furans.

  DOI：

  10.1021/jo00025a012
• 作为产物：
  描述：

  2-(trimethylsilyl)-4-furaldehyde 、 溴代十二烷 在 ammonium chloride 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 生成 4-(1-hydroxytridecyl)-2-trimethyl-silylfuran
  参考文献：
  名称：

  Anti-inflammatory furanones

  摘要：

  新的呋喃酮化合物具有抗炎、免疫抑制和抗增殖活性，并可用于治疗牛皮癣和调节钙稳态。该发明的一种化合物是4-(1-硫代乙酰氧基十三烷基-5-羟基-2(5H)-呋喃酮)。

  公开号：

  US05089485A1

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。
• Process of using anti-inflammatory furanones as selective calcium
  申请人：Allergan, Inc.

  公开号：US05376676A1

  公开（公告）日：1994-12-27

  4-(C.sub.10 -C.sub.20)alkyl-2(5H)-furanone compounds are selective calcium channel inhibitors and useful for treatment of diseases such as hypertension, angina, cardiac arrythmia, pulmonary hypertension, aortic insufficiency, Raynand's disease, migraine headaches, deficiency of platelet function, atherosclerosis, ischemia, reprofusion injury, bronchial asthma, esophageal spasm, dysmenorhea, allergic contact dermatitis, acute inflammatory response, glaucoma and as potentiators of chemotherapeutic agents in the treatment of tumors.

  4-(C.sub.10 -C.sub.20)烷基-2(5H)-呋喃酮类化合物是选择性钙通道抑制剂，可用于治疗高血压、心绞痛、心律失常、肺动脉高压、主动脉瓣不全、雷诺病、偏头痛、血小板功能缺陷、动脉粥样硬化、缺血、再灌注损伤、支气管哮喘、食管痉挛、痛经、过敏性接触性皮炎、急性炎症反应、青光眼，并在肿瘤治疗中作为化疗药物的增效剂。
• Anti-inflammatory 2-furanones
  申请人：Allergan, Inc.

  公开号：US05045564A1

  公开（公告）日：1991-09-03

  New 2-furanone compounds have calcium channel antagonist activity and are useful as anti-inflammatory agents and in treating psoriasis.

  新的2-呋喃酮化合物具有钙通道拮抗活性，可用作抗炎药物，并用于治疗牛皮癣。
• 4-ethyl and 4-ethenyl-5-hydroxy-2(5H)-furanones substituted on alpha
  申请人：Allergan, Inc.

  公开号：US05013850A1

  公开（公告）日：1991-05-07

  Compounds of Formula 1, and of Formula 2, ##STR1## in which R.sub.1 is H or alkyl of 1 to 20 carbon, CO--R.sub.1 * CO--O--R.sub.1 * CO--NH--R.sub.1 * or PO(OR.sub.1 *).sub.2 or PO(OR.sub.1 *)R.sub.1 * where R.sub.1 * independently is alkyl of 1 to 20 carbons, phenyl, or substituted phenyl; X is long chain alkyl having at least 5 carbon atoms, long chain alkyl of at least 5 carbons substituted with an aryl group, or long chain alkyl of at least 5 carbons substituted with a substituted aryl group; Y is COOH, COOR.sub.2, CONH.sub.2, CONHR.sub.2, CON(R.sub.2).sub.2, CHO, COR.sub.2 ; COCF.sub.3, COCHF.sub.2, CH.dbd.NR.sub.2, CR.sub.2 .dbd.N--R.sub.2, CH.dbd.N--NHR.sub.2, CH.dbd.N--N(R.sub.2).sub.2, CH.dbd.NOH, CR.sub.2 .dbd.N--OH, CH.dbd.NOR.sub.2, CR.sub.2 .dbd.NOR.sub.2, CH.sub.2 OH, CHR.sub.2 OH, C(R.sub.2).sub.2 OH, CH.sub.2 OR.sub.2 * CHR.sub.2 OR.sub.2 * C(R.sub.2).sub.2 OR.sub.2 * SO.sub.2 R.sub.2, PO(OR.sub.3).sub.2, and PS(OR.sub.3).sub.2, where R.sub.2 independently is alkyl, phenyl, or substituted phenyl, R.sub.2 * is alkyl, phenyl, substituted phenyl, alkanoyl, or aroyl, and R.sub.3 is H, alkyl, phenyl or substituted phenyl; W is H, alkyl, phenyl, COOH, COOR.sub.4, CONHR.sub.4, CON(R.sub.4).sub.2, and Z is H or alkyl, are disclosed. The compounds possess anti-inflammatory activity.

  化合物的化学式1和化学式2如下：##STR1## 其中R.sub.1为H或含有1至20个碳原子的烷基，CO--R.sub.1 * CO--O--R.sub.1 * CO--NH--R.sub.1 *或PO(OR.sub.1 *).sub.2或PO(OR.sub.1 *)R.sub.1 *，其中R.sub.1 *独立地为含有1至20个碳原子的烷基、苯基或取代苯基；X为至少含有5个碳原子的长链烷基、至少含有5个碳原子的长链烷基取代的芳基、或至少含有5个碳原子的长链烷基取代的取代芳基；Y为COOH、COOR.sub.2、CONH.sub.2、CONHR.sub.2、CON(R.sub.2).sub.2、CHO、COR.sub.2、COCF.sub.3、COCHF.sub.2、CH.dbd.NR.sub.2、CR.sub.2.dbd.N--R.sub.2、CH.dbd.N--NHR.sub.2、CH.dbd.N--N(R.sub.2).sub.2、CH.dbd.NOH、CR.sub.2.dbd.N--OH、CH.dbd.NOR.sub.2、CR.sub.2.dbd.NOR.sub.2、CH.sub.2OH、CHR.sub.2OH、C(R.sub.2).sub.2OH、CH.sub.2OR.sub.2*CHR.sub.2OR.sub.2*C(R.sub.2).sub.2OR.sub.2*SO.sub.2R.sub.2、PO(OR.sub.3).sub.2和PS(OR.sub.3).sub.2，其中R.sub.2独立地为烷基、苯基或取代苯基，R.sub.2 *为烷基、苯基、取代苯基、烷酰基或芳酰基，R.sub.3为H、烷基、苯基或取代苯基；W为H、烷基、苯基、COOH、COOR.sub.4、CONHR.sub.4、CON(R.sub.4).sub.2；Z为H或烷基。这些化合物具有抗炎活性。
• 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。