(1E,2E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one oxime | 78324-39-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (1E,2E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one oxime
• 英文别名: 1-(4-Methoxyphenyl)-3-phenyl-prop-2-en-1-one oxime；(NE)-N-[(E)-1-(4-methoxyphenyl)-3-phenylprop-2-enylidene]hydroxylamine
• CAS: 78324-39-7
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: BOYBMWBBOASQML-IQMJLNOESA-N

物化性质

• 沸点：
  425.0±45.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1E,2E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one oxime 在 乙醚 、 五氯化磷 作用下， 生成 N-(肉桂酰)-4-甲氧基苯胺
  参考文献：
  名称：

  v. Auwers; Seyfried, Justus Liebigs Annalen der Chemie, 1930, vol. 484, p. 194,212

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 乙醇 、 盐酸羟胺 作用下， 生成 (1E,2E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one oxime
  参考文献：
  名称：

  v. Auwers; Seyfried, Justus Liebigs Annalen der Chemie, 1930, vol. 484, p. 194,212

  摘要：

  DOI：

文献信息

• An Easy Access to Oxime Ethers by <scp>Pd‐Catalyzed</scp> C—O <scp>Cross‐Coupling</scp> of Activated Aryl Bromides with Ketoximes and Chalcone Oximes
  作者：Reeta、T. M. Rangarajan、Raj Pal Singh、R. P. Singh、Manjula Singh

  DOI：10.1002/cjoc.201900540

  日期：2020.8

  An efficient Pd‐catalyzed method for C—O cross‐coupling of ketoximes and chalcone oximes with activated aryl bromides and bromo‐chalcones has been developed. All oxime ethers were obtained in good to excellent yields by [(π‐allyl)PdCl]2/t BuXPhos (L7 ) catalyst system. TrixiePhos (L11 ) was also found to be effective for the oxime coupling. This method offers an easy and smooth coupling of chalcone

  已经开发了一种有效的钯催化的方法，用于酮肟和查尔酮肟与活化的芳基溴化物和溴代查耳酮的C-O交叉偶联。通过[（π-烯丙基）PdCl] 2 / t BuXPhos（L7）催化剂体系可以很好地获得所有肟醚。还发现TrixiePhos（L11）对于肟耦合有效。该方法提供了查耳酮肟与活化的芳基溴化物和溴查耳酮的轻松，平滑的偶联，这是以前没有探索过的。
• An Improved, Efficient and Microwave Assisted Synthetic Method for the Synthesis of Chalcone Oximes: An Experimental and Computational Study
  作者：Taner Erdogan、Fatma Oguz Erdogan

  DOI：10.2174/1570178614666170822163132

  日期：2018.1.10

  Chalcone oximes are important molecules in organic chemistry. Extant literature contains several methods for conversion of chalcones to their oxime forms but rapid and efficient new methods need to be developed. In this study; we have investigated a new, microwave assisted synthetic method for conversion of chalcones to their oxime forms. For this purpose, a series of known chalcones were synthesized and converted to their oxime forms employing the method being examined. The results show that the proposed method is efficient, providing time and energy savings. In the second part of our study, DFT calculations with B3LYP method have been performed on the synthesized molecules and computational results have been compared with the experimentally obtained data. All DFT calculations were performed at the B3LYP/6-31G(d), B3LYP/6-311G(d,p) and B3LYP/6-311+G(2d,p) levels of theory. NMR calculations were carried out using GIAO and CSGT methods. Additionally, MEP maps, FMOs, some global reactivity descriptors and Mulliken atomic charges for the synthesized compounds were computationally determined with the same basis sets.

  查耳酮肟在有机化学中是重要的分子。现有文献包含几种将查耳酮转化为肟的方法，但需要开发快速而高效的新方法。在本研究中，我们探索了一种新的微波辅助合成方法，将查耳酮转化为肟形式。为此，合成了一系列已知的查耳酮，并采用正在研究的方法将其转化为肟形式。结果显示，所提出的方法效率高，节省时间和能量。在我们的研究的第二部分，使用B3LYP方法进行了DFT计算，并将计算结果与实验获得的数据进行了比较。所有的DFT计算都在B3LYP/6-31G(d)、B3LYP/6-311G(d,p)和B3LYP/6-311+G(2d,p)理论水平上进行。NMR计算采用GIAO和CSGT方法进行。此外，使用相同的基组，通过计算确定了合成的化合物的MEP图、FMOs、一些全局反应性描述符和Mulliken原子电荷。
• Cascade Synthesis of 3-Functionalized Indoles from Nitrones and Their Conversion to Cycloheptanone-Fused Indoles
  作者：Michelle A. Kroc、Ami Prajapati、Donald J. Wink、Laura L. Anderson

  DOI：10.1021/acs.joc.7b02638

  日期：2018.2.2

  A cascade reaction of N-aryl-α,β-unsaturated nitrones and electron-deficient allenes has been discovered that allows single-step access to 3-functionalized indoles that usually require preformation and alkylation of an indole precursor. The heterocycles prepared through the hydrogen bond donor catalyzed cascade reaction are poised to undergo a McMurry coupling to form previously synthetically elusive

  已发现N-芳基-α，β-不饱和硝酮与缺电子的烯键联的级联反应允许一步一步进入通常需要吲哚前体的预制和烷基化的3-官能化的吲哚。通过氢键供体催化的级联反应制备的杂环准备进行McMurry偶联，以形成先前难以合成的环庚酮-稠合的吲哚。讨论了这些转化的范围以及描述级联反应中间体的机理实验和在级联过程中生成碳立构中心的初始催化不对称实例。
• v. Auwers; Brink, Justus Liebigs Annalen der Chemie, 1932, vol. 493, p. 218,231
  作者：v. Auwers、Brink

  DOI：——

  日期：——
• Notes - Structural Studies of the Isoximes of Weygand and Bauer
  作者：R Barnes、Francis Chigbo

  DOI：10.1021/jo01105a603

  日期：1958.11