(1S)-N-(1-methylethylidene)-1-phenylethylamine | 75815-80-4

• 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: (1S)-N-(1-methylethylidene)-1-phenylethylamine
• 英文别名: (S)-isopropyliden(1-methylbenzyl)amine；(S)-N-α-phenylethylacetonimine；2-propyliden-(S)-1-phenylethylimine；N-[(1S)-1-phenylethyl]propan-2-imine
• CAS: 75815-80-4
• 化学式: C₁₁H₁₅N
• 分子量: 161.247
• InChiKey: XXDGBTARRGRFGV-JTQLQIEISA-N

物化性质

• 沸点：
  225.7±19.0 °C(Predicted)
• 密度：
  0.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S)-N-(1-methylethylidene)-1-phenylethylamine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (S)-N-isopropyl-1-phenylethylamine
  参考文献：
  名称：

  桦木还原过程中二芳基次膦酸-硼烷酰胺的非对映选择性脱对称†

  摘要：

  用碱金属溶液在液氨中处理具有手性酰胺基官能团的二芳基次膦酸-硼烷酰胺会诱导一个芳基取代基在磷上优先脱芳香化，导致形成非等摩尔量的非对映异构体。脱芳香化的非对映选择性很大程度上取决于手性助剂的结构。

  DOI：

  10.1039/c4ob02440k
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 丙酮 以84%的产率得到(1S)-N-(1-methylethylidene)-1-phenylethylamine
  参考文献：
  名称：

  A Simple Diastereoselective Synthesis of Chiral Nonracemic Aliphatic Amines

  摘要：

  开发了一种有效的方法，用于从 (1S)-N-(1-甲基亚乙基)-1-苯乙胺（即源自最简单的酮（丙酮）的席夫碱）非对映选择性合成手性脂肪胺（非对映异构体过量 >96%）和(1S)-1-苯乙胺。该过程包括连续的锂化、烷基化和还原，其特点是在烷基化顺式-Z-亚胺的形成中具有高区域选择性。后者的前手性 C=N 键的氢化物还原主要产生具有 R 构型的光学活性脂肪胺。所有反应均以一锅法进行，无需分离中间产物。

  DOI：

  10.1007/s11178-005-0248-1

文献信息

• A Practical Electrophilic Nitrogen Source for the Synthesis of Chiral Primary Amines by Copper-Catalyzed Hydroamination
  作者：Sheng Guo、Jeffrey C. Yang、Stephen L. Buchwald

  DOI：10.1021/jacs.8b10564

  日期：2018.11.21

  and practical method for the catalytic installation of the amino group across alkenes and alkynes has long been recognized as a significant challenge in synthetic chemistry. As the direct hydroamination of olefins using ammonia requires harsh conditions, the development of suitable electrophilic aminating reagents for formal hydroamination methods is of importance. Herein, we describe the use of 1

  在烯烃和炔烃之间催化安装氨基的温和实用方法长期以来一直被认为是合成化学中的重大挑战。由于使用氨直接对烯烃加氢胺化需要苛刻的条件，因此为正式加氢胺化方法开发合适的亲电胺化试剂具有重要意义。在此，我们描述了使用 1,2-苯并异恶唑作为实用的亲电伯胺源。使用这种杂环作为新的氨基传递剂，开发了一种温和的通用方案，用于氢化铜催化烯烃和炔烃的加氢胺化以形成伯胺。该方法提供了获得广泛的手性 α-支化伯胺和线性伯胺的途径，
• Synthesis of <i>N</i>-alkylated lipopeptides and their application as organocatalysts in asymmetric Michael addition in aqueous environments
  作者：José A. C. Delgado、Fidel E. M. Vicente、Alexander F. de la Torre、Vitor A. Fernandes、Arlene G. Corrêa、Márcio W. Paixão

  DOI：10.1039/d1nj01112j

  日期：——

  through an isocyanide-based multicomponent reaction. Various structural motifs were tunably introduced on the catalyst backbone with the aim of incorporating amphiphilic features. Consequently, they have further been evaluated in the 1,4-addition of aldehydes to trans-β-nitrostyrene having water as the sole solvent. Under sustainable reaction conditions, Michael adducts were obtained in excellent yields

  通过基于异氰化物的多组分反应合成了N-烷基化脂肽有机催化剂库。各种结构基序被可调地引入到催化剂骨架上，目的是结合两亲性特征。因此，它们已在醛与反式-β-硝基苯乙烯的 1,4-加成反应中得到进一步评估，其中水作为唯一溶剂。在可持续的反应条件下，迈克尔加合物以优异的产率、非对映选择性和对映选择性获得，使用低催化剂负载量且无添加剂。
• Enantioselective Intramolecular α‐Arylation of Benzylamine Derivatives: Synthesis of a Precursor to Levocetirizine
  作者：Rakesh K. Saunthwal、Maria Schwarz、Rajendra K. Mallick、William Terry‐Wright、Jonathan Clayden

  DOI：10.1002/anie.202216758

  日期：2023.3.27

  The deprotonation of N′-aryl urea derivatives with a chiral lithium amide base leads to an enantioselective C-arylation of benzylamines. An unusual stereoretentive substitution reaction followed by N-deprotection of the urea forms diarylmethylamine derivatives, including a synthetic intermediate en route to the drug levocetirizine.

  N'-芳基脲衍生物与手性氨基锂碱基的去质子化导致苄胺的对映选择性 C-芳基化。一个不寻常的立体保留取代反应，随后是尿素的N-脱保护，形成二芳基甲胺衍生物，包括合成药物左西替利嗪的中间体。
• Preparation of axially chiral quinolinium salts related to NAD+ models: new investigations of these biomimetic models as ‘chiral amide-transferring agents’
  作者：Stéphane Leleu、Cyril Papamicaël、Francis Marsais、Georges Dupas、Vincent Levacher

  DOI：10.1016/j.tetasy.2004.11.004

  日期：2004.12

  The general purpose of this work is to investigate the potential of biomimetic NAD(+) models as 'nucleophile-transferring agents' with the ultimate motivation to develop new synthetic tools. This first report focuses on the preparation of an axially chiral quinolinium salt 8. A preliminary investigation of these NAD(+) analogues as 'chiral amide-transferring agents' is reported herein. The synthesis of the desired quinolinium salt 8 was first attempted via a Friedlander approach. Given the poor reproducibility of this first synthetic route, a second strategy making use of an intramolecular nickel-catalyzed coupling was developed with success, furnishing the quinolinium salt 8 in 12% overall yield. The potential of the quinolinium salt 8 as a 'chiral amide-transferring agent' was then investigated. Regioselective 1,4-addition of benzylamine and piperidine produced, respectively, adducts 18a and 18b with high diastereoselectivity (de >95%). The resulting 'chiral masked-amide' 18b was reacted with various activated aryl esters affording the corresponding atropisomeric amide 20 with modest atropenantioselectivity (ee = 2-20%). (C) 2004 Elsevier Ltd. All rights reserved.
• Indoles from 3-nitropyridinium salts: A new route to chiral indoles and indolines
  作者：Alexander V Karchava、Marina A Yurovskaya、Thomas R Wagner、Boris L Zybailov、Yuri G Bundel

  DOI：10.1016/0957-4166(95)00379-7

  日期：1995.12

  (S)-1-(1-Methylbenzyl)-2,4,6-trimethylindole was prepared by interaction of (S)isopropyliden(1-methylbenzyl)amine with 1,2,4,6-tetramethyl-3-nitropyridinium iodide. The indoles thus prepared undergo diastereoselective hydride reduction and debenzylation to afford chiral (S)-2,4,6-trimethylindoline with high yield and optical purity up to 76%.