1-(4-苄氧基苯基)丁-1-烯-3-酮 | 75676-91-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(4-苄氧基苯基)丁-1-烯-3-酮
• 英文名称: (E)-4-(4-(benzyloxy)phenyl)but-3-en-2-one
• 英文别名: 1-(4-benzyloxyphenyl)but-1-en-3-one；(E)-4-(4-phenylmethoxyphenyl)but-3-en-2-one
• CAS: 75676-91-4
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: PWNCWNHMBUMBLU-BQYQJAHWSA-N

物化性质

• 沸点：
  430.4±25.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-苄氧基苯基)丁-1-烯-3-酮 在 盐酸肼 、 水 、 sodium ethanolate 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 paraffin oil 为溶剂， 反应 17.0h， 生成 3-(1-(4-fluorobenzyl)-4-(4-(benzyloxy)phenyl)-1H-pyrrol-3-yl)-1H-pyrazole-5-carboxylic acid
  参考文献：
  名称：

  Pyrrolyl Pyrazoles as Non-Diketo Acid Inhibitors of the HIV-1 Ribonuclease H Function of Reverse Transcriptase

  摘要：

  Due to the biological liability of diketo acid (DKA) chain, we transferred this element of our previously reported anti-HIV-1 pyrrolyl derivatives to a non-DKA scaffold, obtaining a series of pyrrolyl-pyrazole carboxylic acids as new RNase H inhibitors. Among the newly synthesized derivatives, oxyphenyl-pyrrolyl-pyrazoles demonstrated inhibitory activities within the low micromolar/submicromolar range with compound 11b being the most potent. Interestingly, all tested compounds showed up to 2 orders of magnitude of selectivity for RNase H vs integrase. Docking studies within the RNase H catalytic site, coupled with site-directed mutagenesis, showed the key structural features that could confer the ability to establish specific interactions within RNase H. Furthermore, they proved the ability of our compounds to interact with amino acids highly conserved among HIV-1 subspecies isolated among patients carrying drug-resistant variants. In the end, the newly discovered pyrazole carboxylic acid derivatives feature promising serum stability with respect to their corresponding DKAs.

  DOI：

  10.1021/acsmedchemlett.9b00617
• 作为产物：
  描述：

  4-苄氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 生成 1-(4-苄氧基苯基)丁-1-烯-3-酮
  参考文献：
  名称：

  Substituted cyclohexanediones and their herbicidal use

  摘要：

  本公开涉及取代环己二酮化合物，所述化合物的制备，含有所述化合物的组合物，以及在各种作物植物存在的情况下使用所述组合物在选择性的前后除草和控制草本杂草上。

  公开号：

  US04983211A1

文献信息

• Asymmetric 1,2-Reduction of Enones with Potassium Borohydride Catalyzed by Chiral <i>N,N</i>′-Dioxide–Scandium(III) Complexes
  作者：Peng He、Xiaohua Liu、Haifeng Zheng、Wei Li、Lili Lin、Xiaoming Feng

  DOI：10.1021/ol302430h

  日期：2012.10.5

  The first catalytic enantioselective 1,2-reduction of enones with 0.45 mol equiv potassium borohydride solution catalyzed by a chiral N,N′-dioxide–Sc(III) complex catalyst was accomplished under mild reaction conditions. A number of optically active allylic alcohols were obtained in good to excellent enantioselectivities (up to 95% ee) with nearly quantitative yields.

  在温和的反应条件下，用手性N，N'-二氧化物-Sc（III）络合物催化剂催化的0.45摩尔当量硼氢化钾溶液对烯酮的首次催化对映选择性1,2-还原。以接近定量的产率获得了许多具有良好至优异对映选择性（高达95％ee）的旋光烯丙基醇。
• A General Organocatalytic Enantioselective Malonate Addition to α,β-Unsaturated Enones
  作者：Veit Wascholowski、Kristian Rahbek Knudsen、Claire E. T. Mitchell、Steven V. Ley

  DOI：10.1002/chem.200800673

  日期：2008.7.7

  A general enantioselective organocatalytic conjugate addition procedure of a variety of malonates to alpha,beta-unsaturated enone systems is presented. The reaction is efficiently catalysed by the pyrrolidinyl tetrazole catalyst 1. Cyclic, acyclic and aromatic enones can be used and the reaction with ethyl malonates 3 b provides the Michael addition products in high yields with good to excellent enantioselectivities

  提出了各种丙二酸酯向α，β-不饱和烯酮体系的一般对映选择性有机催化共轭加成方法。该反应被吡咯烷基四唑催化剂1有效地催化。可以使用环状，无环和芳族烯酮，并且与丙二酸乙酯3b的反应以高收率提供了迈克尔加成产物，具有良好的至优异的对映选择性。由于仅使用1.5当量的丙二酸酯作为试剂，因此该反应易于规模化并且操作实用。此外，丙二酸酯加成产物可通过酶促或氢氧化钠介导的方法容易地单脱羧而不会损失对映体过量。
• A novel route to cyclopropyl ketones, aldehydes, and carboxylic acids.
  作者：Karen E. Rodriques

  DOI：10.1016/s0040-4039(00)79644-4

  日期：1991.3

  Cyclopropanation of α,β-unsaturated N-methoxy-N-methyl amides provided the cyclopropyl amides in far superior yields to those obtained with the corresponding ketones. The desired ketones are then readily accessible by the addition of organometallic reagents. Access to a variety functional groups, including aldehydes and carboxylic acids, is also described.

  α，β-不饱和N-甲氧基-N-甲基酰胺的环丙烷化提供的环丙基酰胺的收率远高于用相应的酮获得的收率。然后通过添加有机金属试剂可以容易地获得所需的酮。还描述了对包括醛和羧酸在内的各种官能团的获取。
• Design, synthesis and biological evaluation of optically pure functionalized spiro[5,5]undecane-1,5,9-triones as HIV-1 inhibitors
  作者：Dhevalapally B. Ramachary、Y. Vijayendar Reddy、Atoshi Banerjee、Sharmistha Banerjee

  DOI：10.1039/c1ob06133j

  日期：——

  A single-step amino acid-catalyzed diastereoselective three-component synthesis of optically pure highly functionalized spiro[5,5]undecane-1,5,9-triones preferentially over the four stereoisomers was accomplished in very good yields with >99% ee/de. Preliminary cell culture-based in vivo screening on these molecules revealed that cis-1aca and cis-1jca are better lead compounds for HIV-1 treatment than

  相对于四个立体异构体，优先完成光学纯的高度官能化的螺[5,5]十一烷-1,5,9-三酮的一步一步氨基酸催化的非对映选择性三组分合成，收率非常高，ee> 99％德 基于培养的初步细胞在体内筛选这些分子显示，顺式- 1ACA和顺- 1jca更好铅化合物对HIV-1治疗比已知的抗逆转录病毒药物叠氮胸苷 （AZT）。
• Substituted cyclohexanediones and their herbicidal uses
  申请人：DowElanco

  公开号：US05006159A1

  公开（公告）日：1991-04-09

  The present disclosure is directed to substituted cyclohexanedione compounds, the preparation of said compounds, compositions containing said compounds and the use of said compositions in the selective pre- and postemergent kill and control of grassy weeds in the presence of various crop plants.

  本公开涉及替代环己二酮化合物，所述化合物的制备，含有所述化合物的组合物以及在各种作物植物存在的情况下使用所述组合物在选择性前后除草和控制草类杂草方面的用途。