(6E)-6-(anilinomethylidene)-4-bromocyclohexa-2,4-dien-1-one | 15597-75-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (6E)-6-(anilinomethylidene)-4-bromocyclohexa-2,4-dien-1-one
• 英文别名: (E)-4-bromo-2-[(phenylimino)methyl]phenol；4B2PMP；trans-N-(5-Brom-salicyliden)-anilin；N-Phenyl-5-brom-salicylaldehydimin
• CAS: 15597-75-8
• 化学式: C₁₃H₁₀BrNO
• 分子量: 276.132
• InChiKey: UBWNXKBHOIRKNG-OQLLNIDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,3-二氢呋喃 、 (6E)-6-(anilinomethylidene)-4-bromocyclohexa-2,4-dien-1-one 在 碘 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以91%的产率得到
  参考文献：
  名称：

  Molecular iodine-catalyzed diastereoselective synthesis of cis-fused pyranobenzopyrans and furanobenzopyrans

  摘要：

  A highly efficient method for the diastereoselective synthesis of cis-fused pyranobenzopyrans and furanobenzopyrans via 2 mol % of molecular iodine-catalyzed reaction of o-hydroxybenzaldimines with 3,4-dihydro-2H-pyran and 2,3-dihydrofuran at ambient temperature is described. 2-Butoxy-4-N-aryl-aminobenzopyrans were also synthesized from o-hydroxybenzaldimine and n-butyl vinyl ether using this procedure. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.024
• 作为产物：
  描述：

  苯胺 、 5-溴水杨醛 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 (6E)-6-(anilinomethylidene)-4-bromocyclohexa-2,4-dien-1-one
  参考文献：
  名称：

  分子内氢键化合物的NMR谱-II：β-二酮和邻羟基羰基化合物的席夫碱

  摘要：

  使用NMR光谱法已显示芳香胺和β-二酮的席夫碱（包括含Ph端基的席夫碱）作为酮胺互变异构体存在。衍生自芳族胺和2-羟基-1-萘醛的席夫碱被认为是酮烯胺和烯醇胺形式的平衡混合物。还研究了芳族胺中电子效应对氢键强度的影响。

  DOI：

  10.1016/0040-4020(68)88164-5

文献信息

• Synthesis, structures and catalytic activities of half-sandwich ruthenium complexes based on Schiff Base ligands
  作者：Wei-Guo Jia、Hui Zhang、Tai Zhang、Shuo Ling

  DOI：10.1016/j.inoche.2016.02.001

  日期：2016.4

  A series of half-sandwich ruthenium(II) complexes containing Schiff-base ligands [Ru(p-cymene)LCl] [HL = (E)-4-X-2-((phenylimino)methyl)phenol, X = H (2a); X = CH3 (2b); X = Cl (2c) and X = Br (2d)] have been synthesized and fully characterized by 1H and 13C NMR spectra, elemental analyses and infrared spectrometry. Moreover, the molecular structures of ruthenium complexes 2b and 2c were confirmed by

  摘要 一系列含有席夫碱配体 [Ru(p-cymene)LCl] [HL = (E)-4-X-2-((phenylimino)methyl)phenol, X = H (2a); X = CH3 (2b); X = Cl (2c) 和 X = Br (2d)] 已合成并通过 1H 和 13C NMR 光谱、元素分析和红外光谱进行充分表征。此外，钌配合物2b和2c的分子结构通过单晶X射线衍射方法得到证实。这些半夹心钌配合物是在硼氢化钠还原剂的存在下，在乙醇溶剂中高度催化硝基芳烃氢化成芳香苯胺的过程。值得注意的是，发现配合物 2c 是一种非常有效的还原硝基芳烃化合物的催化剂，具有广泛的官能团兼容性和底物范围。
• (<i>E</i>)-4-Bromo-2-[(phenylimino)methyl]phenol: a new polymorph and thermochromism
  作者：Helen E. Mason、Judith A. K. Howard、Hazel A. Sparkes

  DOI：10.1107/s2053229620011560

  日期：2020.11.1

  A new polymorph of (E)-4-bromo-2-[(phenylimino)methyl]phenol, C₁₃H₁₀BrNO, is reported, together with a low-temperature structure determination of the previously published polymorph. Both polymorphs were found to have an intramolecular O—H...N hydrogen bond between the phenol OH group and the imine N atom, forming an S(6) ring. The crystals were observed to have different colours at room temperature, with the previously published polymorph being more orange and the new polymorph more yellow. The planarity of the molecule in the two polymorphs was found to be significantly different, with dihedral angles (Φ) between the two aromatic rings for the previously published `orange' polymorph of Φ = 1.8 (2)° at 120 K, while the new `yellow' polymorph had Φ = 45.6 (1)° at 150 K. It was also observed that both polymorphs displayed some degree of thermochromism and upon cooling the `orange' polymorph became more yellow, while the `yellow' polymorph became paler upon cooling.

  报告了 (E)-4- 溴-2-[(苯基亚氨基)甲基]苯酚（C13H10BrNO）的一种新的多晶型，同时还对之前发表的多晶型进行了低温结构测定。研究发现，这两种多晶型的苯酚羟基和亚胺 N 原子间都存在分子内 O-H...N 氢键，形成一个 S(6) 环。室温下观察到的晶体颜色不同，以前公布的多晶体呈橙色，而新的多晶体呈黄色。发现这两种多晶体中分子的平面度有很大不同，以前公布的 "橙色 "多晶体在 120 K 时两个芳香环之间的二面角（Φ）为 Φ = 1.8 (2)°，而新的 "黄色 "多晶体在 150 K 时为 Φ = 45.6 (1)°。此外，还观察到两种多晶体都显示出一定程度的热变色现象，冷却后 "橙色 "多晶体变得更黄，而 "黄色 "多晶体则变得更淡。
• Synthesis, Thermal and Antimicrobial Activity of Novel Organic Single Crystal of (E)-4-Bromo-2-[(phenylimino)methyl]phenol compound
  作者：R. IDAMALARSELVI、G. SWETHA、C. RAMACHANDRA RAJA、R. PRISCILLA

  DOI：10.14233/ajchem.2020.22872

  日期：——

  This study focused on kinetic modelling of a specific type of multistep heterogeneous reaction comprising exothermic and endothermic reaction steps, as exemplified by the experimental kinetic curves for the thermal decomposition of (E)-4-Bromo-2-[(phenylimino)methyl]- phenol (4B2PMP) crystal. The crystal was grown by a slow evaporation method. The cell parameters and crystalline perfection of the grown crystal were studied by single and powder X-ray diffractions. Thermal stability and phase change of 4B2PMP crystal were analyzed by TG/DTA. The microhardness study has revealed the soft nature. UV-visible analysis reveals the wide range of optical window of the optical transmission from 199 nm to 1100 nm. The bandgap of the crystal is found to be 3.24 eV. The FESEM of the crystals was spherically shaped and consisted of a core-shell structure with internal aggregates. The antimicrobial activity of title crystal was tested against different microorganisms by disc diffusion method. The results reveal that the title compound have effective antimicrobial activities.

  本研究针对一种特定类型的多步异相反应进行了动力学建模，其中包括放热和吸热反应步骤，以(E)-4-溴-2-[(苯亚甲基)亚胺基]-苯酚（4B2PMP）晶体的热分解实验动力学曲线为例。晶体是通过缓慢蒸发法生长的。单晶和粉末X射线衍射研究了晶体的晶胞参数和晶体完整度。通过TG/DTA分析了4B2PMP晶体的热稳定性和相变。微硬度研究揭示了其柔软性质。UV-可见分析显示了光学透射的宽波长范围，从199 nm到1100 nm。晶体的带隙为3.24 eV。晶体的FESEM呈球形状，由具有内部聚集物的核壳结构组成。通过盘扩散法测试了标题晶体对不同微生物的抗菌活性。结果显示，标题化合物具有有效的抗菌活性。
• IRE-1alpha INHIBITORS
  申请人：MannKind Corporation

  公开号：US20140080832A1

  公开（公告）日：2014-03-20

  Compounds which directly inhibit IRE-1α activity in vitro, prodrugs, and pharmaceutically acceptable salts thereof. Such compounds and prodrugs are useful for treating diseases associated with the unfolded protein response and can be used as single agents or in combination therapies.

  直接抑制IRE-1α活性的化合物、前药及其药学上可接受的盐。这些化合物和前药可用于治疗与未折叠蛋白应答相关的疾病，并可作为单一药物或联合治疗的组分。
• Lanthanum–Catalyzed One–Pot Synthesis of Chromeno–Fused Pyridine/Quinolinone Derivatives
  作者：Kurma Siva Hariprasad、Bhimapaka China Raju

  DOI：10.1002/ejoc.202301265

  日期：2024.3.25

  A facile one–pot method has been developed for the synthesis of chromeno fused pyridine/quinolinone derivatives. The reactions proceeded through the formation C−O, C−N and C−C bonds to form the title compounds. The bio–active compound 6H-chromeno[4,3-b] quinolin-6-one has been prepared by this protocol.

  开发了一种简便的一锅法来合成色烯稠合吡啶/喹啉酮衍生物。反应通过形成CO、CN和CC键进行，形成标题化合物。通过该方案制备了生物活性化合物 6 H -chromeno[ 4,3-b ]quinolin-6-one。