1-phenyl-propane-1,2-dione 1-oxime | 25355-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-phenyl-propane-1,2-dione 1-oxime
• 英文别名: 1-oximino-1-phenyl-2-propanone；1-hydroxyimino-1-phenylpropan-2-one；1-(N-hydroxyimino)-1-phenylpropan-2-one
• CAS: 25355-34-4
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: YQHWURFNAULYNW-UHFFFAOYSA-N

物化性质

• 熔点：
  165-166 °C(Solv: water (7732-18-5))
• 沸点：
  292.5±13.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  3

制备方法与用途

制备方法

本方法适用于液晶材料、农药中间体和香料中间体的制备。

用途简介

暂无具体内容。

反应信息

• 作为反应物：
  描述：

  1-phenyl-propane-1,2-dione 1-oxime 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以40%的产率得到Beta-氨基-Alpha-甲基-苯乙醇
  参考文献：
  名称：

  Discovery of a Novel Class of Selective Non-Peptide Antagonists for the Human Neurokinin-3 Receptor. 2. Identification of (S)-N-(1-Phenylpropyl)-3-hydroxy-2- phenylquinoline-4-carboxamide (SB 223412)

  摘要：

  Optimization of the previously reported 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonist 14, with regard to potential metabolic instability of the ester moiety and affinity and selectivity for the human neurokinin-3 (hNK-3) receptor, is described. The ester functionality could be successfully replaced by the ketone (31) or by lower alkyl groups (Et, 21, or n-Pr, 24). Investigation of the substitution pattern of the quinoline ring resulted in the identification of position 3 as a key position to enhance hNK-3 binding affinity and selectivity for the hNK-3 versus the hNK-2 receptor. All of the chemical groups introduced at this position, with the exception of halogens, increased the hNK-3 binding affinity, and compounds 53 (3-OH, SE 223412, hNK-3-CHO binding K-i = 1.4 nM) and 55 (3-NHz, hNK-3-CHO binding K-i = 1.2 nM) were the most potent compounds of this series. Selectivity studies versus the other neurokinin receptors (hNK-8-CHO and hNK-1-CHO) revealed that 53 is about 100-fold selective for the hNK-3 versus hNK-2 receptor, with no affinity for the hNK-1 at concentrations up to 100 mu M. In vitro studies demonstrated that 53 is a potent functional antagonist of the hNK-3 receptor (reversal of senktide-induced contractions in rabbit isolated iris sphincter muscles and reversal of NKB-induced Ca2+ mobilization in CHO cells stably expressing the hNK-3 receptor), while in vivo this compound showed oral and intravenous activity in NK-3 receptor-driven models (senktide-induced behavioral responses in mice and senktide-induced miosis in rabbits). Overall, the biological data indicate that (S)-N-(1-phenylpropyl)-3-hydroxy-2-phenylquinoline-4-carboxamide (53, SE 223412) may serve as a pharmacological tool in animal models of disease to assess the functional and pathophysiological role of the NK-3 receptor and to establish therapeutic indications for non-peptide NK-3 receptor antagonists.

  DOI：

  10.1021/jm980633c
• 作为产物：
  描述：

  苯基丙酮 在 盐酸 、 亚硝酸特丁酯 作用下， 以 乙醚 、 水 为溶剂， 以46%的产率得到1-phenyl-propane-1,2-dione 1-oxime
  参考文献：
  名称：

  无过渡金属的无应变C（sp 3）–C（sp 2）键的无酰化解离：从酮和醛到氰基和脂肪族腈的无氰化物访问

  摘要：

  首先描述了一种无过渡金属的脱酰基C（sp 3）–C（sp 2）键裂解的方法，该方法用于合成和实际的酮和醛氧化胺化成腈，使用廉价且商业上充裕的NaNO 2作为氧化剂和氮源。可以从酮和醛中以高收率平稳地获得各种带有芳基，杂芳基，烷基和烯基的腈，避免了剧毒的氰化物或过渡金属。

  DOI：

  10.1021/acs.orglett.5b03367

文献信息

• Silica Gel Supported Chromium Trioxide: An Efficient Reagent for Oxidative Cleavage of Oximes to Carbonyl Compounds under Mild Condition
  作者：Pravin M. Bendale、Bhushan M. Khadilkar

  DOI：10.1080/00397910008087368

  日期：2000.2

  Abstract A facile, efficient oxidative deblocking of aldoximes and ketoximes to their corresponding aldehydes and ketones have been achieved by using silica gel supported chromium trioxide.

  摘要 通过使用硅胶负载的三氧化铬，已经实现了醛肟和酮肟轻松、有效地氧化解封为其相应的醛和酮。
• TRIAZOLOPYRAZINE
  申请人：ENGELHARDT Harald

  公开号：US20140142098A1

  公开（公告）日：2014-05-22

  Disclosed are compounds of the formula (I) wherein the groups R 1 to R 3 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation pharmaceutical preparations containing such compounds and their uses as a medicament.

  公开的是具有以下式（I）的化合物，其中基团R1至R3具有权利要求和说明书中给出的含义。本发明的化合物适用于治疗由细胞过度或异常增殖所特征化的疾病，包含这些化合物的制药制剂以及它们作为药物的用途。
• Novel Chiral C2-Symmetric Bisimidazole-N-Oxides as Promising Organocatalysts for Enantioselective Allylation of Aromatic Aldehydes
  作者：Grzegorz Mlostoń、Janusz Jurczak、Piotr Kwiatkowski、Paulina Mucha

  DOI：10.1055/s-0029-1217365

  日期：2009.7

  A series of new, chiral Lewis bases containing imidazole-N-oxide moiety were tested for purposes of asymmetric catalysis. Bisimidazole-N-oxides derived from (1R,2R)- and (1S,2S)-trans-1,2-diaminocyclohexane were used as catalysts in the allylation reaction of aromatic aldehydes with allyltrichlorosilane, which yielded homoallyl alcohols in good yields and with enantioselectivity up to 80% ee. Screening

  出于不对称催化的目的，测试了一系列含有咪唑-N-氧化物部分的新型手性路易斯碱。衍生自 (1R,2R)- 和 (1S,2S)-trans-1,2-二氨基环己烷的双咪唑-N-氧化物用作芳香醛与烯丙基三氯硅烷的烯丙基化反应的催化剂，该反应以良好的收率和对映选择性高达 80% ee。催化剂的筛选表明，取代基的类型及其在咪唑环中的位置对加成过程的对映选择性有至关重要的影响。
• Synthesis of 1,4- and 1,5-Diaryl-1H-Imidazoles
  作者：V. S. Mityanov、V. P. Perevalov、I. I. Tkach

  DOI：10.1007/s10593-014-1621-1

  日期：2015.2

  1,5-diarylimidazoles has been developed. The method is based on the condensation of appropriate α-diketone monooxime with aromatic amines and formaldehyde in the presence of boron trifluoride etherate leading to the formation of stable boron trifluoride complexes of imidazole N-oxides. Further reduction of these complexes led to the formation of corresponding imidazoles.

  已经开发出一种简单的合成1，4-和1，5-二芳基咪唑的方法。该方法基于适当的α-二酮一肟与芳族胺和甲醛在三氟化硼醚化物的存在下缩合，从而形成稳定的咪唑N-氧化物三氟化硼配合物。这些络合物的进一步还原导致形成相应的咪唑。
• Synthesis and Selected Transformations of 1<i>H</i>-Imidazole 3-Oxides Derived from Amino Acid Esters
  作者：Marcin Jasiński、Grzegorz Mlostoń、Anthony Linden、Heinz Heimgartner

  DOI：10.1002/hlca.200890205

  日期：2008.10

  substituted acetate group at N(1) as the chiral unit were prepared by the reaction of α-(hydroxyimino) ketones, α-amino acid methyl esters, and formaldehyde. In an analogous reaction, ethyl 2-(hydroxyimino)-3-oxobutyrate and 1,3,5-trialkylhexahydro-1,3,5-triazines gave 3-oxido-1H-imidazole-4-carboxylates 14, which easily rearranged into the 2-oxo derivatives 15. Selected examples of N-oxides 5 could be transformed

  通过α-（羟基亚氨基）酮，α-氨基酸甲酯和甲醛的反应，制备了一系列在N（1）上具有取代乙酸酯基的旋光活性1 H-咪唑3-氧化物5。在类似的反应中，由2-（羟基亚氨基）-3-氧代丁酸乙酯和1,3,5-三烷基六氢-1,3,5-三嗪生成3-氧代-1 H-咪唑-4-羧酸酯14，它们很容易重新排列成2-氧代衍生物15。选择的实施例Ñ -oxides 5 可以转化成相应的2,3-二氢- 1 H ^ -咪唑-2-硫酮衍生物10经由一个“硫转移反应”，并用阮内-镍还原组氨酸衍生物5i产生了光学活性的2,3-双（咪唑基）丙酸酯12。此外，（1 H-咪唑-1-基）乙酸酯与伯胺的反应产生相应的乙酰胺。