2-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenol | 90922-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenol
• 英文别名: 2-(2′-hydroxyphenyl)-5,6-dihydro-1,3-oxazine
• CAS: 90922-09-1
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: RTMJUNBGVDHELM-UHFFFAOYSA-N

物化性质

• 熔点：
  78-80 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  320.8±25.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 2-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenol 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以65%的产率得到
  参考文献：
  名称：

  Half-sandwich ruthenium complexes with oxygen–nitrogen mixed ligands as efficient catalysts for nitrile hydration reaction

  摘要：

  Three ruthenium(II) p-cymene complexes containing oxygen-nitrogen mixed ligands [Ru(p-cymene)LCI] [HL = 2-(4,5-dihydrooxazol-2-yl)phenol (2a); HL = 2-(4,5-dihydrothiazol-2-yl)phenol (2b); HL = 2-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenol (2c)] have been synthesized and characterized. All half-sandwich ruthenium complexes were fully characterized by H-1 and C-13 NMR spectra, elemental analyses and infrared spectrometry. The molecular structure of ruthenium complex 2c was further confirmed by single crystal X-ray diffraction methods. Furthermore, these half-sandwich ruthenium complexes are active catalysts for the hydration of nitriles to amides in the presence of sodium hydroxide in isopropanol. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2017.09.007
• 作为产物：
  描述：

  2-hydroxy-N-(3-hydroxypropyl)benzamide 在 氯化亚砜 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 以1.2 g的产率得到2-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenol
  参考文献：
  名称：

  Palladium and copper complexes with oxygen–nitrogen mixed donors as efficient catalysts for the Heck reaction

  摘要：

  A simple bidentate ligand, 2-(2'-hydroxyphenyl)-5,6-dihydro-1,3-oxazine, was readily prepared with a two-step synthesis. Two novel complexes of Pd(II) and Cu(II) with this (N,O) oxazine ligand have been prepared and the molecular structures of these complexes have been confirmed by X-ray structure analysis, NMR, IR and UV-Vis spectroscopy. These complexes efficiently catalyze the Heck reaction of aryl halides with olefins at 120 degrees C in 8 h. The reaction conditions for the Heck coupling of iodobenzene with styrene was optimized by varying the amount of the catalyst, reaction temperature, solvent and exogenous base. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.10.040

文献信息

• Identification of Adenosine Deaminase Inhibitors by Metal‐binding Pharmacophore Screening
  作者：Rebecca N. Adamek、Paul Ludford、Stephanie M. Duggan、Yitzhak Tor、Seth M. Cohen

  DOI：10.1002/cmdc.202000271

  日期：2020.11.18

  more rapid drug discovery efforts for this target, an in vitro assay was developed that utilizes the enzymatic conversion of a visibly emitting adenosine analogue to the corresponding fluorescent inosine analogue by ADA, which can be monitored via fluorescence intensity changes. Utilizing this assay, a library of ∼350 small molecules containing metal‐binding pharmacophores (MBPs) was screened in an HTS

  腺苷脱氨酶 (ADA) 是一种人类单核 Zn 2+将腺苷转化为肌苷的金属酶。ADA 是一种经过验证的癌症药物靶点，但最近在开发针对这种酶的新疗法方面的工作很少。缺乏新进展的部分原因是缺乏针对 ADA 的高通量筛选 (HTS) 的合适检测方法。为了促进针对该目标的更快速的药物发现工作，开发了一种体外测定法，该测定法利用 ADA 将可见发射的腺苷类似物酶促转化为相应的荧光肌苷类似物，这可以通过荧光强度变化进行监测。利用该测定，以 HTS 格式筛选了一个包含 350 个包含金属结合药效团 (MBP) 的小分子的文库，以鉴定针对 ADA 的新抑制剂支架。K i值为 26±1 μM。
• A Catalytic Route to Ampakines and Their Derivatives
  作者：Michael Mulzer、Geoffrey W. Coates

  DOI：10.1021/ol200111a

  日期：2011.3.18

  A catalytic domino reaction that efficiently provides access to an important class of heterocycles, the ampakines, is reported. Our approach is based on the cobalt-catalyzed hydroformylation of dihydrooxazines and allows for the facile synthesis of the pharmaceutically interesting compound CX-614 and related substances.

  据报道，催化多米诺骨牌反应可有效地进入重要的一类杂环，即两性霉素。我们的方法基于二氢恶嗪的钴催化加氢甲酰化，可轻松合成可药用的化合物CX-614和相关物质。
• Selective oxidation of sulfides and olefins by a manganese(III) complex containing an N,O-type bidentate oxazine ligand
  作者：Mojtaba Amini、Mojtaba Bagherzadeh、Zeinab Moradi-Shoeili、Davar M. Boghaei、Arkady Ellern、L. Keith Woo

  DOI：10.1080/00958972.2012.761339

  日期：2013.2.1

  manganese(III) complex [(N–O)2Mn(OAc)] was synthesized using 2-(2′-hydroxyphenyl)-5,6-dihydro-1,3-oxazine (N–O) as a bidentate O, N donor. The complex has been characterized by elemental analysis, IR, UV–vis spectroscopy, and X-ray structure analysis. Oxidation of sulfides and epoxidation of olefins, respectively, to their corresponding sulfoxides and epoxides were conducted by this catalyst using urea

  使用 2-(2'-羟基苯基)-5,6-二氢-1,3-恶嗪 (N-O) 作为双齿 O 合成了一种新的锰 (III) 配合物 [(N-O)2Mn(OAc)] , N 供体。该配合物已通过元素分析、IR、UV-vis 光谱和 X 射线结构分析进行表征。硫化物的氧化和烯烃的环氧化分别生成其相应的亚砜和环氧化物是由该催化剂使用过氧化氢尿素作为氧化剂在室温下空气中进行的。该催化剂在氧化反应中是有效的，产生高产率和选择性。
• Synthesis, X-ray studies, DFT calculations and catalytic activity of a novel iron complex containing an N,O-type bidentate oxazine ligand
  作者：Mojtaba Amini、Mohammad Mehdi Haghdoost、Mojtaba Bagherzadeh、Arkady Ellern、L. Keith Woo

  DOI：10.1016/j.poly.2013.05.049

  日期：2013.9

  2-(2′-hydroxyphenyl)-5,6-dihydro-1,3-oxazine (N–O) as a bidentate O,N donor ligand afforded a five-coordinated iron(III) complex, [Fe(N-O) 2 Cl], with a distorted trigonal bipyramidal configuration. The complex [Fe(N-O) 2 Cl] was isolated as an air-stable crystalline solid and was fully characterized, including by single-crystal X-ray structure analysis. The complex [Fe(N-O) 2 Cl] shows very efficient reactivity

  摘要FeCl 3·3H 2 O与2-（2'-羟基苯基）-5,6-二氢-1,3-恶嗪（N–O）作为二齿O，N供体配体的反应提供了五配位铁（III）配合物[Fe（NO）2 Cl]，具有扭曲的三角双锥体构型。分离出复合物[Fe（NO）2 Cl]，为空气稳定的结晶固体，并进行了充分表征，包括通过单晶X射线结构分析。络合物[Fe（NO）2 Cl]在室温下于空气中，使用过氧化氢尿素（UHP）作为氧化剂，在硫化物氧化为相应的亚砜的过程中显示出非常有效的反应性。为了深入了解该复合物的电子结构，实验研究伴随着密度泛函理论（DFT）计算。
• Ligand Design for Isomer-Selective Oxorhenium(V) Complex Synthesis
  作者：Jinyong Liu、Xiaoge Su、Mengwei Han、Dimao Wu、Danielle L. Gray、John R. Shapley、Charles J. Werth、Timothy J. Strathmann

  DOI：10.1021/acs.inorgchem.6b03076

  日期：2017.2.6

  2-(2′-hydroxyphenyl)-2-oxazoline (Hhoz) ligand to increase steric hindrance in the N,N-cis structure, and it was found that substituents as small as −Me completely eliminate the formation of N,N-cis isomers. The generality of the relationship between N,N-trans/cis isomerism and DAs is further established from a literature survey of 56 crystal structures of Re(O)(LN–O)2X, Re(O)(LO–N–N–O)X, and Tc(O)(LN–O)2X

  最近，N，N- -反式的Re（O）（L N-O ）2 X（L N-O =单阴离子N-O螯合物; X = Cl或Br之前被溶剂或醇盐取代）络合物已经发现优于相应的N，N- -顺在经由氧原子转移催化还原高氯酸盐异构体。然而，报道了的Re（O）的方法（L N-O ）2 X合成常常仅产生的N，N- -顺式配合物或混合物反式和顺异构体。这项研究报告了几何启发的配体设计原理，可以有选择地产生N，N- -反式的Re（O）（L N-O ）2个氯络合物。晶体结构的分析显示，这两个L之间的二面角（DAS）N-O的配体N，N- -顺式的Re（O）（L N-O ）2个氯配合物是小于90°，而在DA的最N，N- -反式的配合物是大于90°。可变大小的烷基（-Me，-CH 2 Ph和-CH 2 CY）然后被引入到2-（2'-羟基苯基）-2-恶唑啉（Hhoz）配位体，以增加空间位阻在N，N- -顺式结构，并且发现该取代基一样小-Me完全消除的形成N，N-