methyl 2-trifluoroacetoxyacrylate | 372-35-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-trifluoroacetoxyacrylate
• 英文别名: methyl 2-(2,2,2-trifluoroacetyl)oxyprop-2-enoate
• CAS: 372-35-0
• 化学式: C₆H₅F₃O₄
• 分子量: 198.099
• InChiKey: VLHGLJFMEKDINM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-trifluoroacetoxyacrylate 、 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R)-4-((2S,3R,6S)-6-tert-Butyl-3-fluoro-tetrahydro-pyran-2-yloxy)-2-oxo-pentanoic acid methyl ester 、 (S)-4-((2S,3R,6S)-6-tert-Butyl-3-fluoro-tetrahydro-pyran-2-yloxy)-2-oxo-pentanoic acid methyl ester
  参考文献：
  名称：

  3-Fluoro-6-tert-butyltetrahydropyranosyl Trichloroacetamidates. “Chiral Auxiliary Donors” for Hydroxyalkyl Radicals

  摘要：

  [GRAPHICS]An improved THP-based chiral auxiliary for hydroxyalkyl radicals is reported. The key modifications involve introduction of a fluorine substituent at C-3 to make the acetal center more robust and the use of Schmidt's trichloroacetamidate glycosylation methodology for efficient attachment of the auxiliary to the radical precursor. The resulting chiral hydroxyalkyl radical equivalents add to methyl 2-trifluoroacetoxyacrylate with selectivities ranging from 9:1 (0 degreesC) to 15:1 (-78 degreesC).

  DOI：

  10.1021/ol049922n
• 作为产物：
  描述：

  甲醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 methyl 2-trifluoroacetoxyacrylate
  参考文献：
  名称：

  Alkyl alpha-fluoroacetoxy acrylates, and polymers thereof

  摘要：

  公开号：

  US02611761A1

文献信息

• A camphor-derived chiral auxiliary for hydroxyalkyl radicals
  作者：Philip Garner、Özge Şeşenoğlu、Hugh Burgoon

  DOI：10.1016/j.tetasy.2003.07.014

  日期：2003.10

  A new camphor-derived chiral auxiliary for hydroxyalkyl radicals is described. The auxiliary is prepared by the Baeyer-Villiger oxidation of 3-fluorocamphor 12 to give lactone 14, followed by its reduction to the lactol 16. Compound 16 is converted to the acetal-ester 17 and then on to radical precursor 18. A key feature of this auxiliary is the incorporation of a fluorine atom at C-3 (pyranoside numbering), which accelerates the Baeyer-Villiger reaction, results in complete anomeric control during auxiliary attachment. and stabilizes the resulting acetal center. The chiral radical derived from carboxylic acid 18 adds to methyl 2-trifluoroacetoxyacrylate to give adducts 22 and 23 with good diastereocontrol (ds from 3:1 at 0 degreesC up to 4.5:1 at -78 degreesC). (C) 2003 Elsevier Ltd. All rights reserved.
• Hydrogel material
  申请人：PBH, INC.

  公开号：EP0495603B1

  公开（公告）日：1998-10-14
• US5362768A
  申请人：——

  公开号：US5362768A

  公开（公告）日：1994-11-08