2-((tert-butylamino)methyl)phenol | 60399-04-4

• 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: 2-((tert-butylamino)methyl)phenol
• 英文别名: 2-[(Tert-butylamino)methyl]phenol
• CAS: 60399-04-4
• 化学式: C₁₁H₁₇NO
• mdl: MFCD09045784
• 分子量: 179.262
• InChiKey: YXEWBNFFNOODEO-UHFFFAOYSA-N

物化性质

• 熔点：
  35 °C
• 沸点：
  268.0±15.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 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：

  2-((tert-butylamino)methyl)phenol 在 六氯环三磷腈 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以56%的产率得到4,4,6,6-tetrachloro-3-tert-butyl-3,4-dihydro-spiro[1,3,2-benzoxazaphosphorine][2λ5,4λ5,6λ5][1,3,5,2,4,6]triazatriphosphorine
  参考文献：
  名称：

  Microwave-assisted and conventional synthesis and stereogenic properties of monospirocyclotriphosphazene derivatives

  摘要：

  The reactions of hexachlorocyclotriphosphazene, N3P3Cl6, with N/O donor type N-alkyl or (aryl)-o-hydroxybenzylamines HO(C6H4)CH2NHR(Ar), [R(Ar) = C(CH3)(3) (1), Ph (2)] produce monospirocyclic tetra-chlorocyclotriphosphazenes (1a and 2a). The geminal substituted cyclotriphosphazenes (1b, 1d, 2b and 2d) are obtained from the reactions of 1 equiv. of la and 2a with 2 equiv. of pyrrolidine or morpholine in THF, while the fully substituted phosphazenes (1c, 1e, 2c and 2e) are formed from the reactions of 1a and 2a with the excess pyrrolidine or morpholine in toluene, between 24 and 48 h. The microwave-assisted reactions of la and 2a with excess pyrrolidine or morpholine in toluene afford the fully substituted products with higher yields than those which were obtained by conventional methods. The structural investigations of the compounds have been verified by elemental analyses, ESI-MS, FTIR, H-1, C-13, P-31 NMR and HETCOR techniques. The crystal structure of 2a is determined by X-ray crystallography and the phosphazene ring is in the flattened boat form. Compounds 1b, 1d, 2b and 2d in which the spiro aryloxy moiety provides the one centre of chirality exist as racemates and the chirality has been confirmed by P-31 NMR spectroscopy on addition of a chiral solvating agent (CSA), (S)-(+)-2,2,2-tri-fluoro-1-(9'-anthryl)ethanol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2010.02.002
• 作为产物：
  描述：

  1-(氯甲氧基)-2-甲基苯 在 过氧化苯甲酰 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 、 苯 为溶剂， 反应 54.0h， 生成 2-((tert-butylamino)methyl)phenol
  参考文献：
  名称：

  Nouvelle Voie d'acces aux dihydro-3,4-2H-benzoxazines-1,3

  摘要：

  由伯胺和二卤代化合物制备3,4-二氢-2H-1,3-苯并恶嗪，其方法可导致化合物在位置2和4上不对称地被取代。

  DOI：

  10.1016/s0040-4039(00)88715-8

文献信息

• Alkylation of Amino Acids and Glutathione in Water by <i>o</i>-Quinone Methide. Reactivity and Selectivity
  作者：Emilia Modica、Riccardo Zanaletti、Mauro Freccero、Mariella Mella

  DOI：10.1021/jo0006627

  日期：2001.1.1

  o-Quinone methide (1) has been produced in water both thermally and photochemically from (2-hydroxybenzyl)trimethylammonium iodide (2). Michael addition reactions of 1 to various amines, and sulfides, including amino acids and glutathione have been carried out, obtaining alkylated adducts (3-16) in fairly good to quantitative yields. The reaction rate and selectivity of 1 toward nitrogen and sulfur

  由（2-羟基苄基）三甲基碘化碘（2）在水中通过热化学和光化学方法制得邻醌甲基化物（1）。已经进行了1对各种胺和硫化物（包括氨基酸和谷胱甘肽）的迈克尔加成反应，以相当好的定量收率获得了烷基化的加合物（3-16）。通过激光闪光光解技术研究了在不同pH条件下1与氮和硫亲核试剂的反应速率和选择性，与水合反应竞争。从水（kNu = 5.8 M-1 s-1）到最具活性的亲核试剂（2.8 x 10（8）M-1 s-1，2-巯基乙醇在碱性条件下）传递时，观察到的反应性跨越7个数量级。这些是亲核加成母体邻苯醌甲基化物（1）的首次直接反应速率测量。竞争实验为游离1作为中间体参与热和光化学反应提供了强大的动力学支持。此外，通过加热（9、10、13和14）或通过辐射（9、11-13、16），几种烷基化加合物可再生1。烷基化过程的这种热和光化学可逆性为诸如o-QM分子载体之类的加合物的使用和应用开辟了新的前景。
• Templated Assembly of Chiral Medium-Sized Cyclic Ethers via 8-endo-trig Nucleophilic Cyclization of Cyclopropenes
  作者：Pavel Ryabchuk、Jonathon P. Matheny、Marina Rubina、Michael Rubin

  DOI：10.1021/acs.orglett.6b03068

  日期：2016.12.16

  An efficient approach toward enantioenriched eight-membered heterocycles via the intramolecular formal substitution of bromocyclopropanes with oxygen-based nucleophiles has been developed. The reaction proceeds via a reactive cyclopropene intermediate, which undergoes a rapid 8-endo-trig cyclization affording cis-fused [6.1.0] bicyclic products exclusively. The quaternary chiral center in the cyclopropene

  已经开发了一种通过用氧基亲核试剂将溴环丙烷分子内形式取代来对映富集八元杂环的有效方法。该反应通过反应性环丙烯中间体进行，该中间体经历快速的8-内-trig环化，仅提供顺式稠合的[6.1.0]双环产物。环丙烯中的四元手性中心控制最终产品中其他两个立体中心的构型。
• Oxazine Ring-Related Vibrational Modes of Benzoxazine Monomers Using Fully Aromatically Substituted, Deuterated, ¹⁵N Isotope Exchanged, and Oxazine-Ring-Substituted Compounds and Theoretical Calculations
  作者：Lu Han、Daniela Iguchi、Phwey Gil、Tyler R. Heyl、Victoria M. Sedwick、Carlos R. Arza、Seishi Ohashi、Daniel J. Lacks、Hatsuo Ishida

  DOI：10.1021/acs.jpca.7b05249

  日期：2017.8.24

  1H nuclear magnetic resonance spectroscopy (1H NMR). The IR and Raman spectra of each compound are compared. Further analysis of 15N isotope-exchanged PH-a indicates the influence of the nitrogen isotope on the band position, both experimentally and theoretically. This finding is important for polymerization studies of benzoxazines that utilize vibrational spectroscopy.

  红外光谱（IR）中960–900 cm –1谱带的消失表明了苯并恶嗪树脂的聚合。从历史上看，该谱带归属于与恶嗪环相连的苯的CH平面弯曲。这项研究表明，该带是恶嗪环的O–C 2拉伸和酚环振动模式的混合。3-苯基-3,4-二氢-2 H-苯并[ e ] [1,3]恶嗪（PH-a）和3-（叔丁基）-3,4-二氢-2 H-苯并的振动频率[ e ] [1,3]恶嗪（PH-t）与同位素交换和全取代的化合物进行比较。合成并进行了精细的研究，包括氘代苯并恶嗪单体，15种N-同位素交换的苯并恶嗪单体和全取代的不具有芳族C–H基团的苯并恶嗪单体。各种同位素交换包括苯酚的苯环周围的氘化，恶嗪环上O– CH 2 –N（2）和N– CH 2 –Ar（4）位置的每个CH 2的选择性氘化或同时氘化两个职位。化学结构通过1 H核磁共振波谱（1 H NMR）确认。比较每种化合物的IR和拉曼光谱。进一步分析在实验和理论上，15
• Studies on the benzoxazine series. Part 3—Preparation and13C NMR structural Study of γ Effects of SomeN-substituted 3,4-dihydro-2H-1,3-benzoxazines
  作者：Kari Neuvonen、Kalevi Pihlaja

  DOI：10.1002/mrc.1260280309

  日期：1990.3

  Seventeen N-substituted 3,4-dihydro-2H-1,3-benzoxazines [N-substituent = Et, Pri, But, CH2C6H5 or CH(CH3)C6H5] were prepared and their structures studied in the light of 13C chemical shifts. The γ effects caused by C(α)-methyl or C(α)-phenyl substitution at the heterocyclic ring carbons were found to be valuable structural parameters. By using N-tert-butyl derivatives as models, and by dividing γtot effects into their components, the rotamer populations due to the rotation around the NC(α) bond could be evaluated. The method also allows the configurational assignment of diastereomeric N-α-methylbenzyl derivatives. The effect of the half-chair structure on the 13C NMR parameters is discussed.

  研究人员制备了 17 种 N 取代的 3,4-二氢-2H-1,3-苯并噁嗪[N 取代基 = Et、Pri、But、CH2C6H5 或 CH(CH3)C6H5]，并根据 13C 化学位移研究了它们的结构。研究发现，杂环碳原子上的 C(α)-甲基或 C(α)-苯基取代引起的 γ 效应是有价值的结构参数。通过使用 N-叔丁基衍生物作为模型，并将γtot 效应分成不同的部分，可以评估围绕 NC(α)键旋转所产生的旋转体群。该方法还可以对非对映的 N-α-甲基苄基衍生物进行构型分配。该方法还讨论了半椅结构对 13C NMR 参数的影响。
• [EN] HETEROARYL DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS HÉTÉROARYLES ET LEURS UTILISATIONS
  申请人：JACOBUS PHARMACEUTICAL COMPANY INC

  公开号：WO2014074775A1

  公开（公告）日：2014-05-15

  The present invention relates to antimalarial compounds and their use against protozoa of the genus Plasmodium, including drug-resistant Plasmodia strains. This invention further relates to compositions containing such compounds and a process for making the compounds.

  本发明涉及抗疟疾化合物及其对疟原虫属Plasmodium的使用，包括抗药性Plasmodia菌株。本发明还涉及含有这种化合物的组合物以及制备这种化合物的过程。