1-(三氟乙酰基)-2-丁烯 | 103935-62-2

• 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
• 中文名称: 1-(三氟乙酰基)-2-丁烯
• 英文名称: crotyl trifluoroacetate
• 英文别名: Trifluoressigsaeure-(but-2t-enylester)；2-butenyl trifluoroacetate；1-(trifluoroacetyl)-2-butene；Crotyl alcohol, trifluoroacetate；[(E)-but-2-enyl] 2,2,2-trifluoroacetate
• CAS: 103935-62-2
• 化学式: C₆H₇F₃O₂
• 分子量: 168.116
• InChiKey: XBSBZMNVXMVAHP-NSCUHMNNSA-N

物化性质

• 沸点：
  120.1±35.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)
• 保留指数：
  737.6

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(三氟乙酰基)-2-丁烯 生成 dimethyl 2-(1-methylallyl)malonate
  参考文献：
  名称：

  SILVERMAN G. S.; STRICKLAND S.; NICHOLAS K. M., ORGANOMETALLICS, 5,(1986) N 10, 2117-2124

  摘要：

  DOI：
• 作为产物：
  描述：

  巴豆醇 、 三氟乙酸酐 以80%的产率得到1-(三氟乙酰基)-2-丁烯
  参考文献：
  名称：

  烯丙醇和胺衍生物的区域选择性羟基磺化

  摘要：

  在烯丙基胺的烯丙基酯或酰胺的存在下，乙酸锰与二苯甲二硫在二氯甲烷-三氟乙酸中的反应产生三氟乙酰氧基硫化物，并因此通过易水解的邻位羟基硫化物进行反应。可以通过选择乙酰基或三氟乙酰基衍生物来控制区域化学结果。

  DOI：

  10.1016/s0040-4039(00)85193-x

文献信息

• Copper(I) promoted CC bond forming reactions: direct activation of allyl alcohols
  作者：Jubaraj.B. Baruah、Ashoka G. Samuelson

  DOI：10.1016/0022-328x(89)87015-9

  日期：1989.2

  Allylic alcohols, acetates, carbonates and chlorides can be activated by copper(I) salts towards nucleophilic substitution by carbon nucleophiles under relatively mild conditions.

  烯丙醇，乙酸盐，碳酸盐和氯化物可以在相对温和的条件下被铜（I）盐活化，以被碳亲核试剂亲核取代。
• C–O and C–S bond activation of allyl esters, ethers, and sulfides by low valent ruthenium complexes
  作者：Jose Giner Planas、Tsuyoshi Marumo、Yoichi Ichikawa、Masafumi Hirano、Sanshiro Komiya

  DOI：10.1016/s1381-1169(99)00139-9

  日期：1999.11

  Allyl carboxylates or ethers react with Ru(cod)(cot) (1) [cod: 1,5-cyclooctadiene, cot: 1,3,5-cyclooctatriene] in the presence of monodentate tertiary phosphines such as PMe3, PEt3, PMe3Ph or PMePh2 to give a series of neutral (eta(3)-allyl)ruthenium(II) complexes Ru( eta(3)-C3H5)(OCOCF3)(PR3)(3) [PR3 = PEt3 (2a), PMe3 (2b), PMe2Ph (2c), PMePh2 (2d)], Ru(eta(3)-C3H5)(OCOR')(PMe3)(3) [R' = Me (2e), Ph (2f)], Ru(eta(3)-syn-C3H4R)(OCOCF3)(PMe3)(3) [R = Me (2g), Ph (2h)] and Ru(OAr)(eta(3)-C3H5)(PMe3)(3) [Ar = Ph (3a), C6H4-o-Me (3b), C6H4-o-Et (3c), C6H4-o-OMe (3d)], whereas similar reactions of these allyl ethers, sulfides and carboxylates in the presence of the bidentate depe ligand [depe = 1,2-bis(diethylphosphino)ethane] afford the cationic (eta(3)-allyl)ruthenium(II) complexes, [Ru(eta(3)-C3H5)(depe)(2)](+)[RY](-) [RY = PhS (4a), MeS (4b), PhO (4c), CF,COO (4d), CH,COO (4e)]. Protonolysis of all (eta(3)-allyl)ruthenium(II) and (eta(3)-crotyl)ruthenium(II) complexes with HCL liberate propylene and trans-2-butene, respectively. Complex 2a reacts with benzaldehyde to give 1-phenyl-3-butene-1-ol. Reaction of 2b with CO forces the bonding mode of allyl moiety in 2a from eta(3) to eta(1). (C) 1999 Elsevier Science B.V. All rights reserved.
• Vitagliano, Aldo; Akermark, Björn; Hansson, Sverker, Organometallics, 1991, vol. 10, # 8, p. 2592 - 2599
  作者：Vitagliano, Aldo、Akermark, Björn、Hansson, Sverker

  DOI：——

  日期：——
• Claisen rearrangement of α-(F-alkyl)enol ethers prepared via Wittig olefination of allyl perfluoroalkanoates
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Shen-Weng Wu、Abderrahim M'Bida、Toshiro Shintani、Takeshi Nakai

  DOI：10.1016/s0040-4039(00)76656-1

  日期：1994.5

  The title rearrangement is shown to proceed at ca. 100 degrees C to afford the gamma,delta-unsaturated perfluoroalkyl ketones. The stereochemistry of the Wittig and claisen processes and the effect of the Rf-group in the Claisen process are discussed.
• Sjoergen, Magnus P. T.; Frisell, Haakan; Aakermark, Bjoern, Organometallics, 1997, vol. 16, p. 942 - 950
  作者：Sjoergen, Magnus P. T.、Frisell, Haakan、Aakermark, Bjoern、Norrby, Per-Ola、Eriksson, Lars、Vitagliano, Aldo

  DOI：——

  日期：——