(E)-1-phenyl-2-(thiophen-2-ylmethylene)hydrazine | 39677-96-8

• 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: (E)-1-phenyl-2-(thiophen-2-ylmethylene)hydrazine
• 英文别名: thiophene-2-carboxaldehyde phenylhydrazone；2-Thiophenecarbaldehyde phenylhydrazone；N-[(E)-thiophen-2-ylmethylideneamino]aniline
• CAS: 39677-96-8
• 化学式: C₁₁H₁₀N₂S
• 分子量: 202.28
• InChiKey: ROJRSTYMUAGWKC-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (E)-1-phenyl-2-(thiophen-2-ylmethylene)hydrazine 在 sodium amide 、 xylene 作用下， 生成 N-phenyl-N'-(N-phenyl-thiophene-2-carboximidoyl)-urea
  参考文献：
  名称：

  Robev, Chemische Berichte, 1958, vol. 91, p. 244

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙酰基噻吩 在 copper(l) iodide 、 氧气 作用下， 以 二甲基亚砜 为溶剂， 反应 22.0h， 生成 (E)-1-phenyl-2-(thiophen-2-ylmethylene)hydrazine
  参考文献：
  名称：

  化学选择性氧化C（CO）？CuI分子氧催化甲基酮的C（甲基）键裂解为醛

  摘要：

  醛类终止反应：铜催化的甲基酮到醛的新型转化已经完成。该方法适用于多种芳香族和脂肪族甲基酮，并能化学选择性地产生醛类，并伴随着副产物氢（H 2）和二氧化碳（CO 2）的释放。

  DOI：

  10.1002/anie.201305010

文献信息

• Simple and efficient approach for synthesis of hydrazones from carbonyl compounds and hydrazides catalyzed by meglumine
  作者：Mo Zhang、Ze-Ren Shang、Xiao-Tang Li、Jia-Nan Zhang、Yong Wang、Kang Li、Yang-Yang Li、Zhan-Hui Zhang

  DOI：10.1080/00397911.2016.1258476

  日期：2017.1.17

  ABSTRACT A simple, environmentally benign protocol for synthesis of hydrazones from carbonyl compounds and hydrazides has been developed in the presence of meglumine in aqueous-ethanol media at room temperature. The salient features of the present protocol are mild reaction conditions, short reaction time, high yields, operational simplicity, metal-free, applicability toward large-scale synthesis, and biodegradable

  摘要 在葡甲胺存在的情况下，在室温下，在乙醇水溶液中，已经开发出一种简单、环境友好的方案，用于从羰基化合物和酰肼合成腙。本协议的显着特点是反应条件温和、反应时间短、产量高、操作简单、不含金属、适用于大规模合成以及可生物降解且价格低廉的催化剂。图形概要
• <i>sp</i> 2-C-H Acetoxylation of Diversely Substituted (<i>E</i> )-1-(Arylmethylene)-2-phenylhydrazines Using PhI(OAc)₂ as Acetoxy Source at Ambient Conditions
  作者：Goutam Brahmachari、Indrajit Karmakar

  DOI：10.1002/ejoc.201900994

  日期：2019.9.15

  It's Simple! Catalyst‐ and additive‐free regioselective direct sp2 C–H acetoxylation of biologically interesting aldehyde hydrazones to access a new series of hydrazone acetates has been achieved. The reaction proceeds at ambient temperature employing PIDA as an acetoxy source.

  很简单！已实现了对生物感兴趣的乙的无催化剂和无添加剂的区域选择性直接sp 2 C–H乙酰化反应，从而获得了一系列新的acetate乙酸盐。使用PIDA作为乙酰氧基源，反应在环境温度下进行。
• X=Y-ZH Systems as potential 1,3-dipoles
  作者：Ronald Grigg、Marie Dowling、Maurice W. Jordan、Visuvanathar Sridharan、Sunit Thianpatanagul

  DOI：10.1016/s0040-4020(01)87793-0

  日期：——

  Hydrazones of aldehydes and ketones undergo intermolecular cycloaddition to electronegative olefins via azomethine imines, formed by a formal 1,2-prototropic shift, in low to moderate yield on heating in xylene or ethanol. In some instances the reaction is diverted to give products derived (at least formally) from an ene reaction. Similar intramolecular cycloadditions occur with unactivated terminal

  醛和酮的dra通过在正式的1,2-质子转移反应中形成的偶氮甲亚胺，在二甲苯或乙醇中加热时，产率低至中等，从而发生分子间环加成反应。在某些情况下，使反应转向以产生（至少正式地）衍生自烯反应的产物。未活化的末端烯烃和炔烃也会发生类似的分子内环加成反应。
• Determination of the Apparent Molar Refraction and Partial Molar Volume at Infinite Dilution of Thiophene-, Pyrrole- and Furan-2-Carboxaldehyde Phenylhydrazone Derivatives in Acetonitrile at 293.15 K
  作者：Ysaías J. Alvarado、José Caldera-Luzardo、Gladys Ferrer-Amado、Victoria Mancilla-Labarca、Elba Michelena

  DOI：10.1007/s10953-006-9093-2

  日期：2007.1.5

  High-precision densitometry and high-accuracy refractometry measurements of extremely dilute solutions of the thiophene-2- (TCPH), pyrrole-2- (PCPH) and furan-2-carboxaldehyde-phenylhydrazone (FCPH) compounds in acetonitrile have been obtained at 293.15 K. The partial molar volumes V 2^∞ of each compound at infinite dilution were determined. The apparent molar refraction of these solutes at infinite dilution at 293.15 K has been experimentally determined within the Kohner-Geffcken-Grunwald-Haley approximation. The volumetric and refractometric results were interpreted in terms of the Pauling electronegativity and intrinsic molar volume of the heteroatom, and the aromaticity of the heterocyclic rings. The experimental results indicate that solute-solute interactions are negligible within the concentration range studied. Theoretical calculations at the DFT-B3LYP/6−311++G(3d,3p) level of molecular volumes support the interpretation that the volumetric contribution from the solute-solvent interactions to the limiting partial molar volumes of solutes are very small and thus solute molecules are isolated in this medium.

  在 293.15 K 的温度下，对噻吩-2-（TCPH）、吡咯-2-（PCPH）和呋喃-2-甲醛苯腙（FCPH）化合物在乙腈中的极稀释溶液进行了高精度密度测量和高精度折射测量。根据 Kohner-Geffcken-Grunwald-Haley 近似法，实验测定了这些溶质在 293.15 K 时无限稀释时的表观摩尔折射率。根据杂原子的鲍林电负性和固有摩尔体积以及杂环的芳香性解释了体积测定法和折射测定法的结果。实验结果表明，在所研究的浓度范围内，溶质与溶质之间的相互作用可以忽略不计。DFT-B3LYP/6-311++G(3d,3p) 级别的分子体积理论计算支持这样的解释，即溶质-溶剂相互作用对溶质极限部分摩尔体积的体积贡献非常小，因此溶质分子在这种介质中是孤立的。
• Base‐Mediated Generation of Ketenimines from Ynamides: Addition of Hydrazones to Give Acetimidohydrazides**
  作者：Capucine Mahe、Agathe C. A. D'Hollander、Kevin Cariou

  DOI：10.1002/ejoc.202200028

  日期：2022.5.13

  The addition of hydrazones onto the central carbon of the ketenimines generated in situ from N-Boc ynamides is reported. This reaction takes place under basic conditions and heating, to generate the N-arylketenimines, and gives access to a variety of acetimidohydrazides.

  报道了将腙添加到由N -Boc ynamides原位产生的酮亚胺的中心碳上。该反应在碱性条件和加热下发生，生成N-芳基烯酮亚胺，并得到多种乙酰亚氨基酰肼。