4-(p-acetamidophenyl)but-3-en-2-one | 55420-72-9

• 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: 4-(p-acetamidophenyl)but-3-en-2-one
• 英文别名: 4-(4-ACETYLAMINOPHENYL)-BUT-3-EN-2-ONE；trans-4-(4-Acetamidophenyl)-but-3-en-2-on；4'-(3-Oxo-1-butenyl)acetanilide；N-[4-[(E)-3-oxobut-1-enyl]phenyl]acetamide
• CAS: 55420-72-9
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: AMXOFEWEPYFRPN-ONEGZZNKSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  440.8±28.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(p-acetamidophenyl)but-3-en-2-one 在 nicotinamide adenine dinucleotide phosphate 作用下， 以 phosphate buffer 、 乙二醇甲醚 、 异丙醇 为溶剂， 反应 2.0h， 以70%的产率得到(2S,3E)-4-(4-acetamidophenyl)-3-buten-2-ol
  参考文献：
  名称：

  Chiral (R)- and (S)-allylic alcohols via a one-pot chemoenzymatic synthesis

  摘要：

  Chiral (R)- and (S)-allylic alcohols with an enantiomeric excess exceeding 99% have been prepared in good to high overall isolated yields through a two-step one-pot chemoenzymatic process based on the palladium-catalyzed Heck reaction of aryl iodides with butenone followed by an enzymatic reduction of the resultant vinylic substitution products. Alcohol dehydrogenases from Lactobacillus brevis and Thermoanaerobacter species were used to attain (R)- and (S)-stereoselectivity, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.043
• 作为产物：
  描述：

  N-(4-碘苯基)乙酰胺 、 丁烯酮 在 palladium diacetate 三(2,4,6-三甲氧基苯基)磷 、 1,8-双二甲氨基萘 作用下， 生成 4-(p-acetamidophenyl)but-3-en-2-one
  参考文献：
  名称：

  Chiral (R)- and (S)-allylic alcohols via a one-pot chemoenzymatic synthesis

  摘要：

  Chiral (R)- and (S)-allylic alcohols with an enantiomeric excess exceeding 99% have been prepared in good to high overall isolated yields through a two-step one-pot chemoenzymatic process based on the palladium-catalyzed Heck reaction of aryl iodides with butenone followed by an enzymatic reduction of the resultant vinylic substitution products. Alcohol dehydrogenases from Lactobacillus brevis and Thermoanaerobacter species were used to attain (R)- and (S)-stereoselectivity, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.043

文献信息

• [EN] QUINAZOLINONE DERIVATIVES<br/>[FR] DERIVES DE QUINAZOLINONE
  申请人：CELLTECH R&D LTD

  公开号：WO2004018462A1

  公开（公告）日：2004-03-04

  A compound of formula (1): wherein: X is an oxygen or sulfur atom; R1 is an aliphatic, cycloaliphatic or cycloalkyl-alkyl-group; R2 is an optionally substituted heteroaromatic group or a -CN group; R3 is a group -(Alk1)mL1(Alk2)nR6 in which m and n, which may be the same or different, is each zero or the integer 1, Alk1 and Alk2, which may be the same or different, is each an optionally substituted aliphatic or heteroaliphatic chain, L1 is a covalent bond or a linker atom or group and R6 is a hydrogen atom or an optionally substituted cycloaliphatic, heterocycloaliphatic, aromatic or heteroaromatic group; R4 is a group -(Alk3)pL2(Alk4)qR7 in which p and q, which may be the same or different, is each zero or the integer 1, Alk3 and Alk4, which may be the same or different, is each an optionally substituted aliphatic or heteroaliphatic chain, L2 is a covalent bond or a linker atom or group and R7 is a hydrogen or halogen atom or a -CN group or an optionally substituted cycloaliphatic, heterocycloaliphatic, aromatic or heteroaromatic group; R5 is a hydrogen atom or an optionally substituted aliphatic group; and the salts, solvates, hydrates, tautomers, isomers or N-oxides thereof. The compounds of the present invention are potent inhibitors of IMPDH.

  翻译结果如下： 公式(1)的化合物：其中：X是氧原子或硫原子；R1是脂肪族、环脂肪族或环烷基-烷基团；R2是可选地取代的杂芳基团或-CN基团；R3是组-(Alk1)mL1(Alk2)nR6，其中m和n相同或不同，都是零或整数1，Alk1和Alk2相同或不同，都是可选地取代的脂肪族或杂脂肪族链，L1是共价键或连接原子或团，R6是氢原子或可选地取代的环脂肪族、杂环脂肪族、芳香族或杂芳族团；R4是组-(Alk3)pL2(Alk4)qR7，其中p和q相同或不同，都是零或整数1，Alk3和Alk4相同或不同，都是可选地取代的脂肪族或杂脂肪族链，L2是共价键或连接原子或团，R7是氢或卤素原子或-CN基团或可选地取代的环脂肪族、杂环脂肪族、芳香族或杂芳族团；R5是氢原子或可选地取代的脂肪族团；以及其盐、溶剂化物、水合物、互变异构体、同分异构体或N-氧化物。本发明的化合物是IMPDH的强效抑制剂。
• The palladium-catalysed vinylic substitution of vinyl triflates with β-substituted-α,β-unsaturated carbonyl compounds. An application to the synthesis of cardenolides
  作者：Antonio Arcadi、Sandro Cacchi、Giancarlo Fabrizi、Fabio Marinelli、Paola Pace

  DOI：10.1016/0040-4020(96)00303-1

  日期：1996.5

  Vinyl triflates react with β-substituted-α,β-unsaturated aldehydes, ketones, and esters in the presence of catalytic amounts of Pd(OAc)2 and an exeess of KOAc, omitting phosphine ligands, to give vinylic substitution products in good to high yield with high regioselectivity. The added vinyl unit is preferentially linked to the β-carbon atom. As to the stereochemistry, vinylic substitution products

  在催化量的Pd（OAc）2和KOAc的存在下，乙烯基三氟甲磺酸酯与β-取代的α，β-不饱和醛，酮和酯反应，省去了膦配体，从而得到了高至高的乙烯基取代产物具有高区域选择性的收率。添加的乙烯基单元优先连接至β-碳原子。关于立体化学，乙烯基取代产物在预先存在的β-取代基的同一侧上含有羰基。事实证明，使用KOAc不仅优于叔胺，而且在添加或不添加盐（例如LiCl和n -Bu 4）的情况下均优于碳酸或碳酸氢盐碱。NCl。报道了该反应在腰果内酯衍生物的合成中的应用。根据β-取代的α，β-不饱和羰基化合物的性质，该反应可产生氢乙烯基化（正式的共轭加成）产物。
• Morpholinium Trifluoroacetate-Catalyzed Aldol Condensation of Acetone with both Aromatic and Aliphatic Aldehydes
  作者：Kristina Zumbansen、Arno Döhring、Benjamin List

  DOI：10.1002/adsc.200900902

  日期：——

  We report a highly efficient, general and practical method for the aldol condensation of acetone with aromatic and aliphatic aldehydes, using morpholinium trifluoroacetate as a catalyst.

  我们报告了一种高效，通用和实用的方法，用于将丙酮与芳香族和脂肪族醛醛醇醛缩合，使用三氟乙酸吗啉鎓作为催化剂。
• Use of (S)-5-(2-Methylpyrrolidin-2-yl)-1H-tetrazole as a Novel and Enantioselective Organocatalyst for the Aldol Reaction
  作者：Sok-Teng (Amy) Tong、Paul W. R. Harris、David Barker、Margaret A. Brimble

  DOI：10.1002/ejoc.200700834

  日期：2008.1

  The novel organocatalyst (S)-5-(2-methylpyrrolidin-2-yl)-1H-tetrazole (4) catalyzes the aldol reaction between acetone and various aldehydes with superior enantioselectivity to the existing organocatalysts (S)-proline (1) and (S)-5-(pyrrolidin-2-yl)-1H-tetrazole (3). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  新型有机催化剂 (S)-5-(2-methylpyrrolidin-2-yl)-1H-tetrazole (4) 催化丙酮和各种醛之间的醛醇反应，对现有有机催化剂 (S)-脯氨酸 (1) 和(S)-5-(吡咯烷-2-基)-1H-四唑(3)。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• CLIFTON, J. E.;COLLINS, I.;HALLETT, P.;HARTLEY, D.;LUNTS, L. H. C.;WICKS,+, J. MED. CHEM., 1982, 25, N 6, 670-679
  作者：CLIFTON, J. E.、COLLINS, I.、HALLETT, P.、HARTLEY, D.、LUNTS, L. H. C.、WICKS,+

  DOI：——

  日期：——