2-(tert-butyldimethylsilyl)-3-hydroxymethyl-4-furaldehyde | 125849-83-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(tert-butyldimethylsilyl)-3-hydroxymethyl-4-furaldehyde
• 英文别名: 5-[Tert-butyl(dimethyl)silyl]-4-(hydroxymethyl)-3-furaldehyde；5-[tert-butyl(dimethyl)silyl]-4-(hydroxymethyl)furan-3-carbaldehyde
• CAS: 125849-83-4
• 化学式: C₁₂H₂₀O₃Si
• 分子量: 240.374
• InChiKey: MYONDEHHLINJPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(tert-butyldimethylsilyl)-3-hydroxymethyl-4-furaldehyde 在 四丁基氟化铵 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 16.25h， 生成 3-cyanomethyl-4-(2-methoxycarbonylvinyl)furan
  参考文献：
  名称：

  Synthesis of oxa analogs of porphobilinogen (PBG) as probes for mechanistic studies of PBG deaminase

  摘要：

  Three oxa analogs of porphobilinogen (PBG) 2, 27, and 29 were synthesized from 3-hydroxymethylfuran. The target molecules were prepared by introducing first the beta-acetate sidechain, then constructing propionate side chains on the furan nucleus into which the aminomethyl group was introduced at position 2 via the corresponding aldehyde.

  DOI：

  10.1016/s0040-4020(01)88038-8
• 作为产物：
  描述：

  3-呋喃甲醇,2-[(1,1-二甲基乙基)二甲基甲硅烷基]- 、 N,N-二甲基甲酰胺 在 正丁基锂 作用下， 生成 2-(tert-butyldimethylsilyl)-3-hydroxymethyl-4-furaldehyde
  参考文献：
  名称：

  Synthesis of oxa analogs of porphobilinogen (PBG) as probes for mechanistic studies of PBG deaminase

  摘要：

  Three oxa analogs of porphobilinogen (PBG) 2, 27, and 29 were synthesized from 3-hydroxymethylfuran. The target molecules were prepared by introducing first the beta-acetate sidechain, then constructing propionate side chains on the furan nucleus into which the aminomethyl group was introduced at position 2 via the corresponding aldehyde.

  DOI：

  10.1016/s0040-4020(01)88038-8

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4-取代2-呋喃酮是由中间体制备而成，其化学式为：##STR1## 其中，R.sub.1、R.sub.2和R.sub.3独立地为1到6个碳的正烷基或1到6个碳的支链烷基；X为H、OH、NH.sub.2、I或Br；R.sub.4为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.2OH、CH.sub.2NH.sub.2、CH.sub.2CH.sub.2OH、CH.sub.2--CHO、CH.sub.2--COOH或CH.sub.2--COOR.sub.5，R.sub.5为1到6个碳的烷基，但当X为氢时，R.sub.4从以下组中选择：CH.sub.2OH、CH.sub.2NH.sub.2、CH.sub.2CH.sub.2OH、CH.sub.2--CHO或CH.sub.2--COOR.sub.5；##STR2## 其中，R.sub.1、R.sub.2和R.sub.3独立地为1到6个碳的正烷基或1到6个碳的支链烷基，R.sub.5为1到6个碳的烷基；##STR3## 其中，R.sub.1、R.sub.2和R.sub.3独立地为1到6个碳的正烷基或1到6个碳的支链烷基，R.sub.6为苯基或1到6个碳的烷基，且##STR4## R.sub.1、R.sub.2和R.sub.3独立地为1到6个碳的正烷基或1到6个碳的支链烷基。
• Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 1. [1,4] O → C and [1,4] C → O Silyl Migrations of Silyl Ethers and Esters Attached to Furan and Thiophene Rings
  作者：Edward Bures、Patrick G. Spinazzé,、Giovanna Beese、Ian R. Hunt、Christine Rogers、Brian A. Keay

  DOI：10.1021/jo971097j

  日期：1997.12.1

  [1,4] O --> C and [1,4] C --> O rearrangements are described for a variety of furans and thiophenes. Treatment of 3-((silyloxy)methyl)furans and -thiophenes with n-BuLi in HMPA provided 2-silylated-3-(hydroxymethyl)furans and -thiophenes in good to excellent yields. The reaction was shown by crossover studies to proceed via an intramolecular [1,4] O --> C silyl migration. Silyl esters of 3-furoic acids also underwent an intramolecular [1,4] O --> C silyl migration to provide 2-silylated-3-furoic acids in moderate to good yield when treated with a mixture of LDA and HMPA. Finally, the above silyl migrations were shown to be reversible. Treatment of 2-silylated-3-(hydroxymethyl)furans and -thiophenes with NaH in DMF provided 3-((silyloxy)methyl)furans and -thiophenes in excellent yields via a [1,4] C --> O silyl migration. The [1,4] C --> O silyl migration was also shown to be an intramolecular process by a crossover study.
• The 1,4 C→O silyl migrations of various furan and thiophene systems
  作者：Patrick G. Spinazzé、Brian A. Keay

  DOI：10.1016/s0040-4039(00)99574-1

  日期：——
• A Regioselective Route to 2,3,4-Trisubstituted Furans
  作者：Leo A. Paquette、Ivan Efremov

  DOI：10.3987/com-00-s(k)2

  日期：——
• SPINAZZE, PATRICK G.;KEAY, BRIAN A., TETRAHEDRON LETT., 30,(1989) N4, C. 1765-1768
  作者：SPINAZZE, PATRICK G.、KEAY, BRIAN A.

  DOI：——

  日期：——