(E)-1,1,1-trichloro-4-(furan-2-yl)but-3-en-2-one | 1280199-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-1,1,1-trichloro-4-(furan-2-yl)but-3-en-2-one
• CAS: 1280199-18-9
• 化学式: C₈H₅Cl₃O₂
• 分子量: 239.485
• InChiKey: PKGKDORSZAIAIZ-ONEGZZNKSA-N

物化性质

• 熔点：
  42-44 °C
• 沸点：
  245.0±40.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1,1,1-trichloro-4-(furan-2-yl)but-3-en-2-one 在 (5aR,10bS)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2S,3S)-N¹,N⁵-dibenzyl-3-(furan-2-yl)-2-methylpentanediamide
  参考文献：
  名称：

  Enantioselective NHC-Catalyzed Redox [4 + 2]-Hetero-Diels–Alder Reactions Using α,β-Unsaturated Trichloromethyl Ketones as Amide Equivalents

  摘要：

  alpha,beta-Unsaturated trichloromethyl ketones are suitable a alpha,beta-unsaturated amide and ester equivalents in N-heterocyclic carbene (NHC)-catalyzed redox hetero-Diels Alder reactions with azolium enolates generated from alpha-aroyloxyaldehydes. The initially formed syn-dihydropyranone products can be isolated or can undergo ring-opening with benzylamine followed by aminolysis of the resulting CCl3 ketone to form a range of diamides with high diastereo- and enantioselectivity (up to >95:5 dr and >99% ee).

  DOI：

  10.1021/acs.joc.5b01820
• 作为产物：
  描述：

  反-3-(2-呋喃基)丙烯醛 在 manganese(IV) oxide 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (E)-1,1,1-trichloro-4-(furan-2-yl)but-3-en-2-one
  参考文献：
  名称：

  Highly enantioselective synthesis of α-trichloromethyldihydropyrans catalyzed by bifunctional organocatalysts

  摘要：

  The enantioselective Michael addition of alpha-cyanoketones to alpha,beta-unsaturated trichloromethyl ketones was firstly reported. With a phenylalanine-derived bifunctional piperazine/thiourea catalyst, a series of alpha-trichloromethyldihydropyrans were obtained with up to 95% ee and 99% yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.043

文献信息

• Isothiourea-Catalyzed Enantioselective Functionalization of 2-Pyrrolyl Acetic Acid: Two-Step Synthesis of Stereodefined Dihydroindolizinones
  作者：Shuyue Zhang、James E. Taylor、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1021/acs.orglett.8b02423

  日期：2018.9.7

  Catalytic enantioselective functionalization of 2-pyrrolyl acetic acid with trichloromethyl enones using isothiourea catalysis is reported, leading to a range of stereodefined diesters and diamides after nucleophilic ring opening with either methanol or benzylamine (30 examples, up to >95:5 dr and >99:1 er). Subsequent intramolecular Friedel–Crafts reaction allows access to dihydroindolizinones in high yields

  据报道，使用异硫脲催化三氯甲基烯酮对2-吡咯基乙酸的催化对映选择性官能化，导致在用甲醇或苄基胺亲核开环后产生一系列立体定义的二酯和二酰胺（30个实例，高达> 95：5 dr和> 99 ：1 er）。随后的分子内Friedel-Crafts反应可实现高收率和立体保真度的二氢吲哚并酮（6个实例，高达> 95：5 dr和99：1 er）。
• Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents
  作者：Louis C. Morrill、Daniel G. Stark、James E. Taylor、Siobhan R. Smith、James A. Squires、Agathe C. A. D'Hollander、Carmen Simal、Peter Shapland、Timothy J. C. O'Riordan、Andrew D. Smith

  DOI：10.1039/c4ob01788a

  日期：——

  Isothiourea HBTM-2.1 catalyses the Michael addition–lactonisation of 2-aryl and 2-alkenylacetic acids and α,β-unsaturated trichloromethyl ketones. Ring-opening of the resulting dihydropyranones and subsequent alcoholysis of the CCl3 ketone with an excess of methanol gives a range of diesters in high diastereo- and enantioselectivity (up to 95 : 5 dr and >99% ee). Sequential addition of two different

  异硫脲 HBTM-2.1 催化 2-芳基和 2-烯基乙酸和 α,β-不饱和三氯甲基酮的迈克尔加成-内酯化。所得二氢吡喃酮的开环和随后用过量甲醇对 CCl 3酮进行醇解得到一系列具有高非对映和对映选择性的二酯（高达 95 : 5 dr 和 >99% ee）。将两种不同的亲核试剂依次添加到二氢吡喃酮上，得到相应的不同取代的二酸衍生物。
• Highly enantioselective synthesis of α-trichloromethyldihydropyrans catalyzed by bifunctional organocatalysts
  作者：Hai-Feng Wang、Peng Li、Hai-Feng Cui、Xiao-Wei Wang、Jun-Kang Zhang、Wen Liu、Gang Zhao

  DOI：10.1016/j.tet.2011.01.043

  日期：2011.3

  The enantioselective Michael addition of alpha-cyanoketones to alpha,beta-unsaturated trichloromethyl ketones was firstly reported. With a phenylalanine-derived bifunctional piperazine/thiourea catalyst, a series of alpha-trichloromethyldihydropyrans were obtained with up to 95% ee and 99% yield. (C) 2011 Elsevier Ltd. All rights reserved.
• Enantioselective NHC-Catalyzed Redox [4 + 2]-Hetero-Diels–Alder Reactions Using α,β-Unsaturated Trichloromethyl Ketones as Amide Equivalents
  作者：Nassilia Attaba、James E. Taylor、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1021/acs.joc.5b01820

  日期：2015.10.2

  alpha,beta-Unsaturated trichloromethyl ketones are suitable a alpha,beta-unsaturated amide and ester equivalents in N-heterocyclic carbene (NHC)-catalyzed redox hetero-Diels Alder reactions with azolium enolates generated from alpha-aroyloxyaldehydes. The initially formed syn-dihydropyranone products can be isolated or can undergo ring-opening with benzylamine followed by aminolysis of the resulting CCl3 ketone to form a range of diamides with high diastereo- and enantioselectivity (up to >95:5 dr and >99% ee).