(3R)-3-(tert-butyldimethylsilyl)oxy-4,4,4-trifluorobutan-1-ol | 189439-67-6

• 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: (3R)-3-(tert-butyldimethylsilyl)oxy-4,4,4-trifluorobutan-1-ol
• 英文别名: (R)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,4,4-trifluorobutanol；(3R)-3-[tert-butyl(dimethyl)silyl]oxy-4,4,4-trifluorobutan-1-ol
• CAS: 189439-67-6
• 化学式: C₁₀H₂₁F₃O₂Si
• 分子量: 258.356
• InChiKey: FAEPYVQMJKYKIJ-MRVPVSSYSA-N

物化性质

• 沸点：
  222.4±40.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R)-3-(tert-butyldimethylsilyl)oxy-4,4,4-trifluorobutan-1-ol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 三氯异氰尿酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (3R)-3-(tert-butyldimethylsilyl)oxy-4,4,4-trifluorobutan-1-al
  参考文献：
  名称：

  Synthesis of trifluoromethylated analogues of β-l-fucofuranose and β-l-4,6-dideoxyxylohexopyranose

  摘要：

  Efficient strategy to trifluoromethylated trans-disubstituted alkene 3 was developed starting from commercially available 4,4,4-trifluoro-3-oxobutyric acid ethyl ester 12. 6-Deoxy-6,6,6-trifluorosugars 21 and 30 were synthesized from 3 in high stereoselectivity and in a straightforward fashion. The key steps were Sharpless AD reaction, regioselective ring opening of trifluoromethylated cyclic sulfate, Horner-Wadsworth-Emmons reaction and TEMPO oxidation. It was noteworthy that the oxidation of alcohols 20 and 29 followed by deprotection and acetylation gave the single isomer target molecules 21 and 30, respectively. (C) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.11.018
• 作为产物：
  描述：

  ethyl (R)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,4,4-trifluorobutanoate 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 以61%的产率得到(3R)-3-(tert-butyldimethylsilyl)oxy-4,4,4-trifluorobutan-1-ol
  参考文献：
  名称：

  Enzymatic Synthesis of Both Enantiomers of 2-Methylene-4-(fluoromethyl)-4-butanolides

  摘要：

  DOI：

  10.1021/jo981183z

文献信息

• Oxazolidin-2-one derivatives, preparation method therefor and
  申请人：Synthelabo

  公开号：US05969146A1

  公开（公告）日：1999-10-19

  Compounds derived from oxazolidin-2-one of formula (I) ##STR1## in which: R.sub.1 represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, a fluoroalkyl group, a hydroxyfluoroalkyl group, a cyanoalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenylmethyl group or an R.sub.3 A- group in which R.sub.3 is a cycloalklyl or cyclooxyalkyl group which is unsubstituted or substituted by a hydroxyl group and A is a --CH.sub.2 or --CH.sub.2 --CH.sub.2 radical, R.sub.2 represents a hydrogen atom or a methyl group, X represents an oxygen or sulphur atom or an NR.sub.4 group where R.sub.4 is an alkyl group or a hydrogen atom, and Z represents an oxygen atom or a --CH.dbd.CH or --CH.sub.2 --CH.sub.2 group, their process of preparation and their applications in therapeutics.

  从氧唑啉-2-酮衍生的化合物，其化学式为（I）##STR1##其中：R.sub.1代表氢原子、烷基、羟基烷基、氟烷基、羟基氟烷基、氰基烷基、取代或未取代苯基、取代或未取代苯甲基或R.sub.3 A-基团，其中R.sub.3是未取代或取代的环烷基或环氧烷基，A是--CH.sub.2或--CH.sub.2--CH.sub.2基团，R.sub.2代表氢原子或甲基，X代表氧原子、硫原子或NR.sub.4基团，其中R.sub.4是烷基或氢原子，Z代表氧原子或--CH.dbd.CH或--CH.sub.2--CH.sub.2基团，它们的制备过程及在治疗学中的应用。
• Enzymatic Synthesis of Both Enantiomers of 2-Methylene-4-(fluoromethyl)-4-butanolides
  作者：Yuzo Komatsu、Fumio Sasaki、Satoshi Takei、Tomoya Kitazume

  DOI：10.1021/jo981183z

  日期：1998.10.1
• Synthesis of trifluoromethylated analogues of β-l-fucofuranose and β-l-4,6-dideoxyxylohexopyranose
  作者：Bing-Lin Wang、Fei Yu、Xiao-Long Qiu、Zhong-Xing Jiang、Feng-Ling Qing

  DOI：10.1016/j.jfluchem.2005.11.018

  日期：2006.5

  Efficient strategy to trifluoromethylated trans-disubstituted alkene 3 was developed starting from commercially available 4,4,4-trifluoro-3-oxobutyric acid ethyl ester 12. 6-Deoxy-6,6,6-trifluorosugars 21 and 30 were synthesized from 3 in high stereoselectivity and in a straightforward fashion. The key steps were Sharpless AD reaction, regioselective ring opening of trifluoromethylated cyclic sulfate, Horner-Wadsworth-Emmons reaction and TEMPO oxidation. It was noteworthy that the oxidation of alcohols 20 and 29 followed by deprotection and acetylation gave the single isomer target molecules 21 and 30, respectively. (C) 2005 Elsevier B.V. All rights reserved.