1-(三氟乙酰基)-2-哌啶酮 | 94363-58-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-(三氟乙酰基)-2-哌啶酮
• 英文名称: 1-(Trifluoroacetyl)piperidin-2-one
• 英文别名: 1-(2,2,2-trifluoroacetyl)piperidin-2-one
• CAS: 94363-58-3
• 化学式: C₇H₈F₃NO₂
• 分子量: 195.141
• InChiKey: GEPLDFXBBIXQLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  1-(三氟乙酰基)-2-哌啶酮 在 4-二甲氨基吡啶 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 tert-butyl (E)-3-benzylidene-2-oxopiperidine-1-carboxylate
  参考文献：
  名称：

  SpinPhox /铱（I）催化的环状α-亚烷基羰基化合物的不对称加氢

  摘要：

  带有α-手性碳中心的旋光中型环状羰基化合物在制药科学和不对称合成中引起人们的兴趣。在本文中，SpinPhox / Ir I催化剂在环外α，β-不饱和环状羰基化合物（包括各种α-亚烷基内酰胺，不饱和环状酮）中的CC键的不对称氢化中被证明具有高度对映选择性。内酯。值得注意的是，该方法可以成功地用于具有六元或七元环的具有挑战性的α-烷基亚内酰胺底物的不对称氢化，从而提供相应的具有α-手性碳中心的旋光羰基化合物，其对映体过量通常非常好（高达ee的98％ ）。该协议的合成用途还已在抗炎药洛索洛芬及其类似物以及生物学上重要的ε-氨基己酸衍生物的不对称合成中得到证明。

  DOI：

  10.1002/anie.201309521
• 作为产物：
  描述：

  哌啶酮 、 三氟乙酸酐 以 甲苯 为溶剂， 反应 1.0h， 生成 1-(三氟乙酰基)-2-哌啶酮
  参考文献：
  名称：

  SpinPhox /铱（I）催化的环状α-亚烷基羰基化合物的不对称加氢

  摘要：

  带有α-手性碳中心的旋光中型环状羰基化合物在制药科学和不对称合成中引起人们的兴趣。在本文中，SpinPhox / Ir I催化剂在环外α，β-不饱和环状羰基化合物（包括各种α-亚烷基内酰胺，不饱和环状酮）中的CC键的不对称氢化中被证明具有高度对映选择性。内酯。值得注意的是，该方法可以成功地用于具有六元或七元环的具有挑战性的α-烷基亚内酰胺底物的不对称氢化，从而提供相应的具有α-手性碳中心的旋光羰基化合物，其对映体过量通常非常好（高达ee的98％ ）。该协议的合成用途还已在抗炎药洛索洛芬及其类似物以及生物学上重要的ε-氨基己酸衍生物的不对称合成中得到证明。

  DOI：

  10.1002/anie.201309521

文献信息

• Natural α-methylenelactam analogues: Design, synthesis and evaluation of α-alkenyl-γ and δ-lactams as potential antifungal agents against Colletotrichum orbiculare
  作者：Wang Delong、Wang Lanying、Wu Yongling、Song Shuang、Feng Juntao、Zhang Xing

  DOI：10.1016/j.ejmech.2017.02.050

  日期：2017.4

  In our continued efforts to improve the potential utility of the alpha-methylene-gamma-lactone scaffold, 62 new and 59 known natural alpha-methylenelactam analogues including alpha-methylene-gamma- lactams, alpha-arylidene- gamma and delta-lactams, and 3-arylideneindolin-2-ones were synthesized as the bioisosteric analogues of the amethylenelactone scaffold. The results of antifungal and cytotoxic activity indicated that among these derivatives compound (E)-1-(2, 6-dichlorobenzyl)-3-(2-fluorobenzylidene) pyrrolidin-2-one (Py51) possessed good selectivity with the highest antifungal activity against Colletotrichum orbiculare with IC50 - 10.4 mu M but less cytotoxic activity with IC50 - 141.2 mu M (against HepG2 cell line) and 161.2 mu M ( against human hepatic L02 cell line). Ultrastructural change studies performed by transmission electron microscope showed that Py51 could cause important cell morphological changes in C. orbiculare, such as plasma membrane detached from cell wall, cell wall thickening, mitochondria disruption, a dramatic increase in vacuolation, and eventually a complete loss in the integrity of organelles. Significantly, mitochondria appeared one of the primary targets, as confirmed by their remarkably aberrant morphological changes. Analysis of structureeactivity relationships revealed that incorporation of the aryl group into the alpha-exo methylene and the N-benzyl substitution increased the activity. Meanwhile, the alpha-arylidene-gamma-lactams have superiority in selectivity over the 3-arylideneindolin-2-ones. Based on the results, the N- benzyl substituted a-(2-fluorophenyl)-gamma-lactam was identified as the most promising natural- based scaffold for further discovering and developing improved crop- protection agents. (c) 2017 Elsevier Masson SAS. All rights reserved.
• Stereoselective Process for a CCR3 Antagonist
  作者：Tai-Yuen Yue、Douglas D. McLeod、Kevin B. Albertson、Steven R. Beck、Joerg Deerberg、Joseph M. Fortunak、William A. Nugent、Lilian A. Radesca、Liya Tang、Cathie Dong Xiang

  DOI：10.1021/op050202l

  日期：2006.3.1

  A convergent, multikilogram, stereoselective synthesis of 1 is described. A key fragment, (S)-3-(4-fluorobenzyl)piperidine (2) was synthesized from valerolactam in three steps using our recently discovered Ir-BDPP-catalyzed asymmetric hydrogenation. Another key fragment, (IR,2R)-2-(benzyloxycarbonylamino)cyclohexanecarboxaldehyde (3) was synthesized from meso-hexahydrophthalic anhydride in seven steps. The stereochemistry was set in the first step of this sequence via a quinidine-mediated desymmetrization of the meso-anhydride. Coupling of the fragments 2 and 3 followed by deprotection provided the penultimate 23. The active pharmaceutical ingredient (API) free base I was obtained by treatment of 23 with the aminothiazole fragment 4 under mild conditions.
• Enantioselective Hydrogenation of 3-Alkylidenelactams:  High-Throughput Screening Provides a Surprising Solution
  作者：Tai-Yuen Yue、William A. Nugent

  DOI：10.1021/ja028043y

  日期：2002.11.1

  High-throughput screening of 256 potential catalysts (8 metal precursors x 32 phosphine ligands) has identified [(BDPP)Ir(COD)]BF4 as a catalyst for the enantioselective hydrogenation of 3-alkylidenelactams. This result is surprising given the highly flexible backbone of the BDPP ligand and the ineffectiveness of this catalyst in other applications. The asymmetric hydrogenation appears fairly general for five- and six-membered lactams and in one case has been scaled up to a 20 kg level.
• Kramarova, E. P.; Shipov, A. G.; Artamkina, O. B., Journal of general chemistry of the USSR, 1984, vol. 54, # 8, p. 1712 - 1713
  作者：Kramarova, E. P.、Shipov, A. G.、Artamkina, O. B.、Baukov, Yu. I.

  DOI：——

  日期：——
• KRAMAROVA, E. P.;SHIPOV, A. G.;ARTAMKINA, O. B.;BAUKOV, YU. I., ZH. OBSHCH. XIMII, 1984, 54, N 8, 1921-1922
  作者：KRAMAROVA, E. P.、SHIPOV, A. G.、ARTAMKINA, O. B.、BAUKOV, YU. I.

  DOI：——

  日期：——