N-(3-氯苯基)-2-羟基苄胺 | 13160-55-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3-氯苯基)-2-羟基苄胺
• 英文名称: N-(3-chlorophenyl)2-hydroxy benzylamine
• 英文别名: N-(3-Chlor-phenyl)-2-hydroxy-benzylamin；2-((3-chlorophenylamino)methyl)phenol；2-(3-chloro-anilinomethyl)-phenol；2-(3-Chlor-anilinomethyl)-phenol；2-{[(3-Chlorophenyl)amino]methyl}phenol；2-[(3-chloroanilino)methyl]phenol
• CAS: 13160-55-9
• 化学式: C₁₃H₁₂ClNO
• mdl: MFCD00020055
• 分子量: 233.697
• InChiKey: GLNKHORJYRGXQS-UHFFFAOYSA-N

物化性质

• 熔点：
  112-114 °C(Solv: methanol (67-56-1))
• 沸点：
  396.8±22.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-氯苯基)-2-羟基苄胺 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2-(4-chlorophenoxy)-3-(3-chlorophenyl)-N-(4-nitrobenzyl)-3,4-dihydro-2H-2l5-benzo[e][1,3,2]oxazaphosphinin-2-imine
  参考文献：
  名称：

  N-[2-(4-卤代苯氧基)-3-(3-氯苯基)-3, 4-dihydro-2H-1,3,2-λ5-benzoxazaphosphinin-2-yliden]-N-取代的合成及光谱表征施陶丁格反应生成的胺

  摘要：

  AbstractThe synthesis of the title compounds was accomplished in four steps. The synthetic route involves the preparation of Schiff's base by reacting salicylaldehyde with m‐chloroaniline in EtOH. The Schiff's base was then reduced with NaBH4/MeOH. In the second step, PCl3 was reacted with p‐chlorophenol/p‐bromophenol in THF in the presence of Et3N to obtain P(III) dichloride derivatives. The reduced Schiff's base and dichloride derivatives were reacted in equimolar quantities in the presence of Et3N in THF to get the cyclized product. Alkyl azides were prepared by reacting alkyl bromides with sodium azide, and then alkyl azides were treated with the cyclized product to obtain the title compounds. The structure of these novel compounds was elucidated by elemental analysis, IR, 1H, 13C, 31P NMR, and mass spectroscopy. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:499–504, 2010; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20639

  DOI：

  10.1002/hc.20639
• 作为产物：
  描述：

  m-chlorophenylsalicylaldimine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 N-(3-氯苯基)-2-羟基苄胺
  参考文献：
  名称：

  通过重排反应进行钯催化的区域选择性C-苄基化：获得苄基取代的苯胺

  摘要：

  据报道，钯催化了前所未有的C-苄基化重排反应。反应通过重排进行，从而直接合成对位或邻位苄基取代的N-甲基苯胺。以高区域选择性获得产物，而无需在催化过程中使用配体。

  DOI：

  10.1002/chem.201603941

文献信息

• Zirconium Borohydride - a Versatile Reducing Agent for the Reduction of Electrophilic and Nucleophilic Substrates
  作者：S. Narasimhan、R. Balakumar

  DOI：10.1080/00397910008087061

  日期：2000.12

  Abstract Zirconium borohydride, a potential reducing agent, reduces acids, esters, imines to the corresponding alcohols and secondary amines in good yield at room temperature within two hours. This facile reducing property was taken advantage off in the synthesis of pheromones and some novel chiral precursors for asymmetric synthesis.

  摘要 硼氢化锆是一种潜在的还原剂，可在室温下两小时内以良好的收率将酸、酯、亚胺还原为相应的醇和仲胺。在信息素和一些用于不对称合成的新型手性前体的合成中利用了这种简便的还原特性。
• Synthesis and Structure-Activity Relationships of a Class of Sodium Iodide Symporter Function Inhibitors
  作者：Fanny Waltz、Lucie Pillette、Elodie Verhaeghe、Yves Ambroise

  DOI：10.1002/cmdc.201100258

  日期：2011.10.4

  Blocking iodide: Iodide capture plays a central role in many thyroid pathophysiological conditions. Here, we report the synthesis and biological evaluation of 184 N‐benzylanilines as iodide transport inhibitors in thyroid‐derived cells. Important structure–activity relationships were elucidated, and two compounds with enhanced potency were identified. These new bioactive molecules are valuable pharmacological

  阻断碘化物：碘化物的捕获在许多甲状腺病理生理状况中起着核心作用。在这里，我们报告了184 N-苄基苯胺作为碘在甲状腺衍生细胞中的转运抑制剂的合成和生物学评估。阐明了重要的构效关系，并鉴定了两种具有增强效价的化合物。这些新的生物活性分子是进一步了解如何在甲状腺中捕获碘化物的有价值的药理学工具，SAR数据可能证明对开发新型抗甲状腺药有用。
• Metal-Free Diaryl Etherification of Tertiary Amines by <i>Ortho</i>-C(sp²)–H Functionalization for Synthesis of Dibenzoxazepines and -ones
  作者：Vellekkatt Jamsheena、Chikkagundagal K. Mahesha、M. Nibin Joy、Ravi S. Lankalapalli

  DOI：10.1021/acs.orglett.7b03328

  日期：2017.12.15

  A phenyliodine(III) diacetate mediated umpolung reactivity of the tertiary amines with suitably substituted o-hydroxybenzyl and phenyl groups is exploited to facilitate o-C(sp2)–H functionalization to afford diaryl ethers. The presence of an o-CHO and secondary amine functionalities in the resulting diaryl ether, generated in situ, were utilized for synthesis of dibenzoxazepines and dibenzoxazepinones

  利用苯乙酸碘（III）介导的叔胺与适当取代的邻羟基苄基和苯基基团的蛋白反应，可促进邻-C（sp 2）-H官能化，从而提供二芳基醚。原位产生的所得二芳基醚中邻-CHO和仲胺官能团的存在被用于合成二苯并x氮杂和二苯并a氮杂酮。温和的条件和相对较宽的底物范围以及二芳基醚进一步多样化的潜力是该方法的重点。
• Synthesis and structure–antibacterial activity relationship studies of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thiones
  作者：Hikmet Agirbas、Berat Kemal、Fatma Budak

  DOI：10.1007/s00044-010-9457-4

  日期：2011.11

  The synthesis and characterization of a series of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thiones were presented. Preliminary in vitro antimicrobial activity of the compounds was assessed against a panel of microorganisms including S. aureus, E. faecalis, P. aeruginosa, E. coli, and C. albicans. Some of the compounds exhibited significantly in vitro antimicrobial activity. The pMIC values were correlated with physicochemical descriptors: Hammett substituent constants (sigma (m) and sigma (p) ) and the lipophilic constant (pi). One statistical significant 2D-QSAR model was obtained with para-substituted compounds. The pMIC values were also correlated with some theoretical descriptors as independent variables and four statistical significant 2D-QSAR models were also obtained with meta-substituted compounds.
• Palladium-Catalyzed Regioselective C-Benzylation via a Rearrangement Reaction: Access to Benzyl-Substituted Anilines
  作者：Manuel Amézquita-Valencia、Howard Alper

  DOI：10.1002/chem.201603941

  日期：2016.11.14

  An unprecedented C‐benzylation rearrangement reaction, catalyzed by palladium, is reported. The reaction proceeds by rearrangement leading to the direct synthesis of para or ortho benzyl‐substituted N‐methylanilines. The product is obtained in high regioselectivity, without the need to use a ligand for the catalytic process.

  据报道，钯催化了前所未有的C-苄基化重排反应。反应通过重排进行，从而直接合成对位或邻位苄基取代的N-甲基苯胺。以高区域选择性获得产物，而无需在催化过程中使用配体。