N-(3-甲氧基苄基)-2-甲基-2-丙胺 | 207349-84-6

• 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-甲氧基苄基)-2-甲基-2-丙胺
• 中文别名: N-(3-甲氧基苄基)叔丁基胺
• 英文名称: N-(3-methoxybenzyl)-2-methylpropan-2-amine
• 英文别名: N-tert-butyl-(3-methoxy)-benzyl amine；N-(3-methoxybenzyl)-tert-butylamine；N-tert-butyl-(3-methoxybenzyl)amine；N-[(3-methoxyphenyl)methyl]-2-methylpropan-2-amine
• CAS: 207349-84-6
• 化学式: C₁₂H₁₉NO
• mdl: MFCD07405541
• 分子量: 193.289
• InChiKey: BAZYXMARGARHPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  265.9±15.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  N-(3-甲氧基苄基)-2-甲基-2-丙胺 在 titanium(III) chloride 、 草酰氯 、 双氧水 、 三乙胺 、 N,N-二甲基甲酰胺 、 三氟乙酸酐 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 、 苯 为溶剂， 反应 2.34h， 生成 2-Tert-butyl-5-methoxy-4-[2-(4-methylphenyl)sulfanylphenyl]-1,4-dihydroisoquinolin-3-one
  参考文献：
  名称：

  Additive and Vinylogous Pummerer Reactions of Amido Sulfoxides and Their Use in the Preparation of Nitrogen Containing Heterocycles

  摘要：

  The alpha-thiocarbocation generated from the Pummerer re action of N-methyl-N-phenyl-2-[2-(toluene-4-sulfinyl)phenyl]acetamide undergoes Friedel-Crafts reaction at the gamma-carbon with the tethered aromatic ring. Reductive removal of the phenylthio group from the resulting product using Raney nickel occurs in high yield, and the overall reaction represents a new method for the synthesis of a variety of 3-phenyl-substituted oxindoles. Treatment of the related N-benzyl-N-alkyl amido sulfoxide system with trifluoroacetic anhydride affords tetrahydroisoquinolone derivatives. The product distribution encountered coincides with the rotamer population of the starting amide. When the N-benzyl-N-methyl amide is used, only the normal Pummerer product is formed. In this case, the thionium ion is generated in the wrong conformation for pi-cyclization to occur. The corresponding N-tert-butyl amido system, however, exists in a geometric orientation which places the benzylic group in the crucial conformation necessary for pi-cyclization, and consequently, the reaction proceeds smoothly. Related cyclization reactions occur in good yield with the corresponding furanyl and cyclohexenyl N-tert-butyl amido sulfoxides. The additive Pummerer reaction of 3-phenylsulfinyl-N-benzyl-N-tert-butylacrylamide gave products derived from both 5- and 6-exo trig cyclizations. Intramolecular electrophilic aromatic substitution via six-membered ring closure ultimately afforded a dihydropyridone. The competitive process involving ipso attack of the aromatic ring on the thionium ion generates a spiro cyclohexadienyl cation that undergoes fragmentation of the adjacent a-bond. The resulting acyl iminium ion is converted to N-tert-butyl-2-phenyl-3-phenylsulfinylacrylamide upon aqueous workup. Only cyclizations leading to five-membered rings occur with the corresponding indolyl and alkenyl N-tert-butyl amido sulfoxides.

  DOI：

  10.1021/jo972093h
• 作为产物：
  描述：

  3-甲氧基苯甲醛 在 氢气 、 四氯化钛 、 tris(2,6-difluorophenyl)borane 作用下， 以 乙醚 、 甲苯 、 苯 为溶剂， 反应 0.25h， 生成 N-(3-甲氧基苄基)-2-甲基-2-丙胺
  参考文献：
  名称：

  沮丧的路易斯对（FLP）催化的亚胺加氢中的结构-反应关系

  摘要：

  的autoinduced，沮丧路易斯对（FLP）16 -苯环的催化的加氢取代Ñ -benzylidene-叔-butylamines与B（2,6-F 2 C ^ 6 ħ 3）3和分子氢是由动力学分析调查。亚胺和相应胺的p K a值是通过量子力学方法确定的，并提供了直接的比例关系。两个速率常数k 1（简单的催化循环）和k 2（自动诱导的催化循环）与p K的相关性亚胺和胺对之间的差异（ΔpK a）或Hammett的σ参数用作建立FLP催化的亚胺加氢反应的结构反应性关系的有用参数。

  DOI：

  10.1002/chem.201600716

文献信息

• Reductive Transformations of Carbonyl Compounds Catalyzed by Rhodium Supported on a Carbon Matrix by using Carbon Monoxide as a Deoxygenative Agent
  作者：Niyaz Z. Yagafarov、Dmitry L. Usanov、Alexey P. Moskovets、Nikolai D. Kagramanov、Victor I. Maleev、Denis Chusov

  DOI：10.1002/cctc.201500493

  日期：2015.9.1

  An efficient method for the rhodium on carbon matrix catalyzed preparation of secondary and tertiary amines, cyanoesters, and nitriles through the reductive amination/alkylation of carbonyl compounds was developed, including a convenient procedure for the tandem formal reductive addition of acetonitrile to aldehydes. The catalyst could be reused, and at least three consecutive reaction cycles were

  开发了一种通过羰基化合物的还原胺化/烷基化铑/碳基体催化仲胺和叔胺，氰基酯和腈的制备方法，包括将乙腈串联正式还原加成到醛中的简便方法。该催化剂可以重复使用，并且以可比的效率进行了至少三个连续的反应循环。已证明该方法与易于被氢和复杂氢化物还原的官能团兼容。
• Access to β-Lactams by Enantioselective Palladium(0)-Catalyzed C(sp³)H Alkylation
  作者：Julia Pedroni、Michele Boghi、Tanguy Saget、Nicolai Cramer

  DOI：10.1002/anie.201405508

  日期：2014.8.18

  Reported here is an asymmetric CH functionalization approach to β‐lactams using readily accessible chloroacetamide substrates. Important aspects of this transformation are challenging C(sp3)C(sp3) and strain‐building reductive eliminations to for the four‐membered ring. In general, the β‐lactams are formed in excellent yields and enantioselectivities using a bulky taddol phosphoramidite ligand in combination

  β-内酰胺由于具有广泛的生物学活性以及易于发生开环反应，因此是非常重要的结构基序。过渡金属催化的CH功能化已成为实现非常规高效断开连接的策略。与Pd 0催化的CH官能化用于芳基-芳基偶联的显着进展相反，涉及形成饱和C（sp 3）C（sp 3）键的相关反应是难以捉摸的。这里报告的是一个不对称的C使用容易获得的氯乙酰胺底物对β-内酰胺进行H官能化方法。这种转变的重要方面是挑战四元环的C（sp 3）C（sp 3）和应变消除。通常，使用大体积的他达酚亚磷酰胺配体与金刚烷基羧酸作为助催化剂，可以以优异的收率和对映选择性形成β-内酰胺。
• Activation of Hydrogen and Hydrogenation Catalysis by a Borenium Cation
  作者：Jeffrey M. Farrell、Jillian A. Hatnean、Douglas W. Stephan

  DOI：10.1021/ja307995f

  日期：2012.9.26

  The readily prepared borenium salt [(IiPr(2))(BC(8)H(14))][B(C(6)F(5))(4)] (2) [IiPr(2) = C(3)H(2)(NiPr)(2)] is shown to activate H(2) heterolytically in the presence of tBu(3)P. Compound 2 also acts as a catalyst for the metal-free hydrogenation of imines and enamines at room temperature.

  容易制备的硼盐 [(IiPr(2))(BC(8)H(14))][B(C(6)F(5))(4)] (2) [IiPr(2) = C( 3)H(2)(NiPr)(2)] 显示在 tBu(3)P 存在下异裂地激活 H(2)。化合物 2 还充当亚胺和烯胺在室温下无金属氢化的催化剂。
• [EN] BORENIUM FRUSTRATED LEWIS PAIR CATALYSTS<br/>[FR] CATALYSEURS DE BORÉNIUM À BASE DE PAIRES FRUSTRÉES DE LEWIS
  申请人：STEPHAN CONSULTING CORP

  公开号：WO2013177708A1

  公开（公告）日：2013-12-05

  A process for the catalytic hydrogenation of a variety of organic substrates using frustrated Lewis pair catalysts comprising a borenium complex is described. The frustrated Lewis pair catalysts described can also be used in a variety of chemical transformations of organic molecules.

  描述了一种利用受挫路易斯酸碱对催化剂进行多种有机底物的催化加氢过程，其中包括硼镎配合物。所述的受挫路易斯酸碱对催化剂还可用于多种有机分子的化学转化。
• Imine hydrogenation by alkylaluminum catalysts
  作者：Jillian A. Hatnean、Jordan W. Thomson、Preston A. Chase、Douglas W. Stephan

  DOI：10.1039/c3cc47889k

  日期：——

  Di-isobutylaluminum hydride and tri-iso-butylaluminum (DIBAL 1, TIBAL 2) are shown to be efficient hydrogenation catalysts for a variety of imines at 100 °C and 100 atm of H2, operating via a hydroalumination/hydrogenolysis mechanism.

  研究表明，氢化二异丁基铝和氢化三异丁基铝（DIBAL 1 和 TIBAL 2）是一种高效的氢化催化剂，可在 100 °C 和 100 atm 的 H2 条件下通过氢化/氢解机理催化多种亚胺。