2-乙基-1-苯基丁烷-1,3-二酮 | 39581-96-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-乙基-1-苯基丁烷-1,3-二酮
• 英文名称: 2-ethyl-1-phenyl-1,3-butanedione
• 英文别名: 2-Ethyl-1-phenylbutane-1,3-dione
• CAS: 39581-96-9
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: LPCGWVBPFSRIFF-UHFFFAOYSA-N

物化性质

• 沸点：
  140 °C
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙基-1-苯基丁烷-1,3-二酮 在 甲醇 、 氨 、 sodium acetate 、 sodium amide 作用下， 以 甲醇 、 苯 为溶剂， 反应 8.5h， 生成 (4-Ethyl-1,5-diphenyl-1H-pyrazol-3-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Novel 1,5-Diphenylpyrazole Nonnucleoside HIV-1 Reverse Transcriptase Inhibitors with Enhanced Activity versus the Delavirdine-Resistant P236L Mutant:  Lead Identification and SAR of 3- and 4-Substituted Derivatives

  摘要：

  Through computationally directed broad screening, a novel 1,5-diphenylpyrazole (DPP) class of HIV-1 nonnucleoside reverse transcriptase inhibitors (NNRTIs) has been discovered. Compound 2 (PNU-32945) was found to have good activity versus wild-type (IC50 = 2.3 mu M) and delavirdine-resistant P236L (IC50 = 1.1 mu M) reverse transcriptase IRT). Also, PNU-32945 has an ED50 for inhibition of viral replication in cell cultures of 0.1 mu M and was shown to be noncytotoxic with a CC50 > 10 mu M. Structure-activity relationship studies on the 3- and 4-positions of PNU-32945 led to interesting selectivity and activity within the class. In particular, the 3-hydroxyethyl-4-ethyl congener 29 is a potent inhibitor of the P236L mutant (IC50 = 0.65 mu M), whereas it is essentially inactive versus the wild-type enzyme (IC50 > 50 mu M). Furthermore, this compound was significantly more active versus the P236L mutant than delavirdine. The synthesis and RT inhibitory activity of various 3- and 4-substituted analogues are discussed.

  DOI：

  10.1021/jm990383f
• 作为产物：
  描述：

  1-苯基-1,3-丁二酮 在 sodium 、 苯 作用下， 生成 2-乙基-1-苯基丁烷-1,3-二酮
  参考文献：
  名称：

  Claisen; Lowman, Chemische Berichte, 1888, vol. 21, p. 1152 Anm. 2

  摘要：

  DOI：

文献信息

• Selective α-Mono- and α,α-Dialkylations of 1,3-Diketones Using Solid Base Prepared from Sodium Ethoxide and Alumina
  作者：Nobutoshi Yoshihara、Teruhiro Kitagawa、Ikuko Ihara、Sadao Hasegawa、Tadashi Hasegawa

  DOI：10.1246/bcsj.65.1185

  日期：1992.4

  The alkylation of 1,3-diketones with alkyl halides using a solid base prepared from sodium ethoxide and alumina was carried out. The amount of 0.4 mol of sodium ethoxide on 50 g of alumina showed the best reactivity for alkylation. Selective mono- and dialkylation could be achieved by controlling the reaction temperature.

  使用由乙醇钠和氧化铝制备的固体碱进行 1,3-二酮与卤代烷的烷基化反应。50 克氧化铝上 0.4 摩尔乙醇钠的量显示出最好的烷基化反应性。通过控制反应温度可以实现选择性单烷基化和二烷基化。
• Mono-C-alkylation of β-dicarbonyl compounds using tetraethylammonium fluoride
  作者：James H. Clark、Jack M. Miller

  DOI：10.1039/c39770000064

  日期：——

  The hydrogen-bonded solvates formed between tetraethylammonium fluoride and a number of β-dicarbonyl compounds react at about room temperature with alkyl iodides to provide high yields of the mono-C-alkylated β-dicarbonyl products with no apparent contamination due to the formation of O-alkyl, dialkyl, or polymerisation products.

  氟化四乙基铵和许多β-二羰基化合物之间形成的氢键合溶剂化物在大约室温下与烷基碘反应，以提供高收率的单碳烷基化β-二羰基产物，且由于形成O而没有明显的污染-烷基，二烷基或聚合产物。
• Palladium(ii)- and platinum(ii)-catalyzed addition of stabilized carbon nucleophiles to ethylene and propyleneElectronic supplementary information (ESI) available: experimental procedures, analytical and spectroscopic data for new compounds. See http://www.rsc.org/suppdata/cc/b3/b316734h/
  作者：Xiang Wang、Ross A. Widenhoefer

  DOI：10.1039/b316734h

  日期：——

  PdCl(2)(CH(3)CN)(2) and [PtCl(2)(H(2)C[double bond]CH(2))](2) catalyze the addition of beta-dicarbonyl compounds to ethylene and propylene.

  PdCl（2）（CH（3）CN）（2）和[PtCl（2）（H（2）C [双键] CH（2））]（2）催化将β-二羰基化合物添加到乙烯中并丙烯。
• Convenient Synthesis of 2-pyridyl thioglycosides
  作者：Galal Elgemeie、Elsayed Eltamny、Ibraheim Elgawad、Nashwa Mahmoud

  DOI：10.3184/030823408x340816

  日期：2008.8

  A reported method for preparation of a new class of pyridine thioglycosides via reaction of pyridine-2(1 H)-thiones with 2,3,4-tri- O-acetyl-α-d-xylo- and -β-d-arabinopyranosyl bromides has been studied.

  据报道，一种通过吡啶-2(1 H)-亚硫酰与 2,3,4- 三 O-乙酰基-α-d-氧基-和-β-d-阿拉伯吡喃糖基溴化物反应制备新型吡啶硫糖苷的方法得到了研究。
• Photo-mediated [1, 3]-Carbonyl shift of β-Ketocarbonyls
  作者：Wenzhao Zhang、Yao Li、Sanzhong Luo

  DOI：10.1016/j.jphotochem.2020.112553

  日期：2020.6

  An organic amine mediated photolytic [1,3]-benzoyl migration of β-benzoyl carbonyl compounds was reported. This migration was achieved by Norrish-Yang cyclization and retro-aldol reaction under black light (365 nm) or visible light irradiation. This photolytic protocol provides an alternative approach to the synthesis of 1,5-dicarbonyl compounds. By chiral primary amine catalysis, a kinetic resolution

  报道了有机胺介导的β-苯甲酰基羰基化合物的光解[1,3]-苯甲酰基迁移。这种迁移是通过在黑光（365 nm）或可见光照射下进行的Norrish-Yang环化反应和逆醛醇反应实现的。该光解方案为合成1,5-二羰基化合物提供了另一种方法。通过手性伯胺催化，还发展了动力学拆分以提供对映体富集的1，5-二羰基。