(E)-1,1,1-trifluoro-4-(2-methoxyphenyl)but-3-en-2-one | 204708-10-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1,1,1-trifluoro-4-(2-methoxyphenyl)but-3-en-2-one
• 英文别名: 1,1,1-Trifluoro-4-(2-methoxyphenyl)-3-buten-2-one
• CAS: 204708-10-1
• 化学式: C₁₁H₉F₃O₂
• 分子量: 230.186
• InChiKey: BHUJHRQSOYXICE-VOTSOKGWSA-N

物化性质

• 沸点：
  190 °C(Press: 5 Torr)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (E)-1,1,1-trifluoro-4-(2-methoxyphenyl)but-3-en-2-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以75%的产率得到(E)-4-(o-anisyl)-1,1,1-trifluoro-3-buten-2-ol
  参考文献：
  名称：

  三氟甲基化π-烯丙基铝配合物亲核取代对区域化学的极性影响

  摘要：

  在钯络合物催化剂的存在下，三氟甲基取代的肉桂酸碳酸丙二酯的烯丙基亲核取代反应在区域和立体选择性上产生了S N 2'产物。在类似的空间环境中，由三氟甲基的极性作用引起的区域化学与甲基化的肉桂基底物相反。与苯基衍生物相比，在空间上更受阻的异丁烯和叔丁基底物也使产物在受阻更严重的位置反应。尽管检查了预期分子内配位会影响区域化学的邻位取代底物，但未检测到其他区域异构体。

  DOI：

  10.1016/s0022-328x(03)00262-6
• 作为产物：
  描述：

  2-ethoxy-4-(2-methoxyphenyl)-6-trifluoromethyl-3,4-dihydro-2H-pyran 300.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 以78%的产率得到(E)-1,1,1-trifluoro-4-(2-methoxyphenyl)but-3-en-2-one
  参考文献：
  名称：

  A Facile Synthesis of 4-Aryl-1,1,1-trifluorobut-3-en-2-ones via 4-Aryl Substituted CF3 - Containing Dihydropyran Derivatives: A Versatile Method for the Introduction of Fluorine-Containing C4- and C6-Unit to Aromatic Compounds

  摘要：

  The CF3 - containing dihydropyran derivative (2) reacted easily with various aromatic compounds in trifluoroacetic acid to give novel 4-aryl substituted dihydropyran derivatives (7) in moderate to high yields. Retro hetero Die Is-Alder reaction of thus obtained 7 proceeded readily by heating at 300 degrees C to afford the corresponding 4-aryl-1,1,1-trifluorobut-3-en-2-ones (12) in good to excellent yields. With the use of p-toluenesulfonic acid instead of trifluoroacetic acid together with dihydropyran (2) in acetonitrile, 4-trifluoroacetyl-1,3-butalienylation of 1,3-dimethoxybenzene occurred successfully. The bimolecular reaction of dihydropyran (2) in the presence of p-toluenesulfonic acid was also examined.

  DOI：

  10.3987/com-09-s(s)60

文献信息

• Highly enantioselective copper(<scp>i</scp>)-catalyzed conjugate addition of 1,3-diynes to α,β-unsaturated trifluoromethyl ketones
  作者：Amparo Sanz-Marco、Gonzalo Blay、M. Carmen Muñoz、José R. Pedro

  DOI：10.1039/c5cc01676b

  日期：——

  The conjugate diynylation of [small alpha],[small beta]-unsaturated trifluoromethyl ketones is carried out in the presence of a low catalytic load (2.5 mol %) of a copper(I)-MeOBIPHEP complex, triethylamine and a terminal 1,3-diyne....

  在低催化负荷（2.5 mol％）的铜（I）-MeOBIPHEP络合物，三乙胺和末端1,3的存在下，进行小α，小β-不饱和三氟甲基酮的共轭二炔化反应。 -狄恩...
• Asymmetric synthesis of either diastereomer of trifluoromethylated allylic amines by the selective reduction of trifluoromethyl α,β-unsaturated N-tert-butanesulfinyl ketoimines
  作者：Zhen-Jiang Liu、Jin-Tao Liu

  DOI：10.1039/b810459j

  日期：——

  Regio- and diastereoselective reduction of chiraltrifluoromethyl α,β-unsaturated N-tert-butanesulfinyl ketoimines 1 was achieved by choosing appropriate reducing agent and either diastereomer of the corresponding trifluoromethylated allylic amines was obtained with good yield and excellent diastereoselectivity (up to >99 : 1 dr).

  通过选择适当的还原剂，实现了手性三氟甲基δ,δ-不饱和 N-叔丁基亚磺酰酮亚胺 1 的区域和非对映选择性还原，并获得了相应的三氟甲基烯丙基胺的非对映异构体，且收率高，非对映选择性极佳（达 >99 : 1 dr）。
• Dy(OTf)3/Pybox-catalyzed enantioselective Friedel–Crafts alkylation of indoles with α,β-unsaturated trifluoromethyl ketones
  作者：Shigeru Sasaki、Takayasu Yamauchi、Kimio Higashiyama

  DOI：10.1016/j.tetlet.2010.02.121

  日期：2010.4

  The first catalytic enantioselective Friedel–Crafts alkylation of indoles with α,β-unsaturated trifluoromethyl ketones has been accomplished. The reaction was achieved in the presence of the Dy(OTf)3/Pybox complex, producing the desired products in high yields (up to 99%) with good enantioselectivities (up to 86% ee). The absolute stereochemistry of the resulting adducts was determined by X-ray analysis

  用α，β-不饱和三氟甲基酮对吲哚进行的首个催化对映选择性Friedel-Crafts烷基化反应已经完成。该反应是在Dy（OTf）3 / Pybox络合物存在下完成的，以高收率（最高99％）和良好的对映选择性（最高86％ee）生产出所需的产物。通过X射线分析确定所得加合物的绝对立体化学。
• Highly Enantioselective Michael Addition of Cyclic 1,3-Dicarbonyl Compounds to β,γ-Unsaturated α-Keto Esters
  作者：Xing-Kuan Chen、Chang-Wu Zheng、Sheng-Li Zhao、Zhuo Chai、Ying-Quan Yang、Gang Zhao、Wei-Guo Cao

  DOI：10.1002/adsc.201000045

  日期：——

  A highly enantioselective Michael addition of cyclic 1,3‐dicarbonyl compounds to β,γ‐unsaturated α‐keto esters catalyzed by amino acid‐derived thiourea‐tertiary‐amine catalysts is presented. Using 5 mol% of a novel tyrosine‐derived thiourea catalyst, a series of chiral coumarin derivatives were obtained in excellent yields (up to 99%) and with up to 96% ee under very mild conditions within a short

  提出了由氨基酸衍生的硫脲-叔胺催化剂催化的环状1,3-二羰基化合物对β，γ-不饱和α-酮酯的高对映选择性迈克尔加成反应。使用5 mol％的新型酪氨酸衍生的硫脲催化剂，可在极短的反应时间内，在非常温和的条件下，以优异的收率（高达99％）和高达96％ee获得一系列手性香豆素衍生物。
• An efficient route to 3-trifluoromethylpyrazole via cyclization/1,5-H shift and its applications in the synthesis of bioactive compounds
  作者：Yongdong Wang、Jing Han、Jie Chen、Weiguo Cao

  DOI：10.1016/j.tet.2015.09.007

  日期：2015.10

  A methodology for regioselective synthesis of 3-trifluoromethylpyrazole from the reaction of trifluoromethyl alkenone and tosylhydrazone has been developed. The reaction was proposed to proceed through a tandem cyclization and 1,5-H shift reaction, which can be applied to the synthesis of bioactive compounds like Celecoxib, Mavacoxib, and SC-560. (C) 2015 Elsevier Ltd. All rights reserved.