(R)-2,2-dimethyl-1-(naphthalen-1-yl)propan-1-amine | 324034-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2,2-dimethyl-1-(naphthalen-1-yl)propan-1-amine
• 英文别名: (R)-2,2-Dimethyl-1-(naphthalen-1-yl)propan-1-amine；(1R)-2,2-dimethyl-1-naphthalen-1-ylpropan-1-amine
• CAS: 324034-55-1
• 化学式: C₁₅H₁₉N
• 分子量: 213.323
• InChiKey: FQTPRCXAYUOOGA-AWEZNQCLSA-N

物化性质

• 沸点：
  333.6±11.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2,2-dimethyl-1-(naphthalen-1-yl)propan-1-amine 在 lithium aluminium tetrahydride 、 甲酸 、 sodium sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.25h， 生成 N,N'-bis((R)-2,2-dimethyl-1-(naphthalen-1-yl)propyl)ethane-1,2-diamine
  参考文献：
  名称：

  对映选择性C–H功能化加成序列提供了重取代的3-氮杂双环[3.1.0]己烷

  摘要：

  公开了对含全氟烷基的3-氮杂双环[3.1.0]己烷的对映选择性CH官能团化方法。模块化且稳定的二氮杂膦烷配体可使用三氟乙酰亚胺基氯化物作为亲电伙伴，实现高度对映选择性的Pd（0）催化的环丙烷C–H功能化。反过来，生成的环状酮亚胺产物与多种亲核试剂以一锅法平稳反应，从而能够快速，模块化地构建重取代的吡咯烷。

  DOI：

  10.1021/jacs.7b07024
• 作为产物：
  描述：

  三甲基乙腈 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 25.5h， 生成 (R)-2,2-dimethyl-1-(naphthalen-1-yl)propan-1-amine
  参考文献：
  名称：

  Preparation of enantiomers of 1-(1-naphthyl)-2,2-dimethylpropylamine and their behaviour as chiral solvating agents: study of diastereochemic association by Job's plots and intermolecular NOE measurements

  摘要：

  Enantiomers of 1-(1-naphthyl)-2,2-dimethylpropylamine have been obtained and considered as chiral solvating agents against several compounds. The formed complexes have been studied with the aid of the nuclear Overhauser effect and its stoichiometry by the method of continuous variations. Two diastereoisomeric complexes present similar geometry of association by pi-pi -stacking of the aromatic rings and by hydrogen bonding of the functional groups. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00334-7

文献信息

• Nickel(0)-Catalyzed Enantioselective Annulations of Alkynes and Arylenoates Enabled by a Chiral NHC Ligand: Efficient Access to Cyclopentenones
  作者：Joachim S. E. Ahlin、Pavel A. Donets、Nicolai Cramer

  DOI：10.1002/anie.201408364

  日期：2014.11.24

  nickel‐catalyzed reductive [3+2] cycloaddition of α,β‐unsaturated aromatic esters and alkynes constitutes an efficient method for their synthesis. Here, nickel(0) catalysts comprising a chiral bulky C1‐symmetric N‐heterocyclic carbene ligand were shown to enable an efficient asymmetric synthesis of cyclopentenones from mesityl enoates and internal alkynes under mild conditions. The bulky NHC ligand

  环戊烯酮是天然产物以及反应性合成中间体的多功能结构基序。镍催化的α，β-不饱和芳族酯和炔烃的还原[3 + 2]环加成反应是合成它们的有效方法。在这里，包含手性庞大的C 1-对称的N-杂环卡宾配体的镍（0）催化剂被证明能够在温和的条件下由均三烯酸酯和内部炔烃有效地不对称合成环戊烯酮。庞大的NHC配体以非常高的对映选择性提供了环戊烯酮产物，并导致不对称取代的炔烃的区域选择性结合。
• Chiral Cyclic Alkyl Amino Carbene (CAAC) Transition-Metal Complexes: Synthesis, Structural Analysis, and Evaluation in Asymmetric Catalysis
  作者：Adrien Madron du Vigné、Nicolai Cramer

  DOI：10.1021/acs.organomet.2c00351

  日期：2022.10.10

  Despite recent advances in the field of cyclic alkyl amino carbenes (CAACs) including a few complementary synthetic strategies affording CAACs with various substitution patterns, the application potential of chiral CAACs to efficiently catalyze asymmetric organometallic transformations remains largely underdeveloped. Herein, we describe a convenient and robust route that incorporates common chiral

  尽管环状烷基氨基卡宾 (CAACs) 领域的最新进展包括一些互补的合成策略，提供具有各种取代模式的 CAACs，但手性 CAACs 在有效催化不对称有机金属转化方面的应用潜力仍然很大程度上未开发。在此，我们描述了一种方便且稳健的路线，该路线包含常见的手性伯胺，允许使用范围广泛的手性 CAAC 前体。以简单的方式获得了与 Cu、Au、Ru、Rh、Ir 和 Pd 相应的过渡金属配合物。通过X射线单晶分析全面收集配合物的空间参数，作为进一步配体设计的信息来源。
• Chiral NHC Ligands for Enantioselective Gold(I) Catalysis Under Aerobic Conditions: the Importance of Conformational Flexibility and Steric Hindrance of NHC Ligand on Reactivity
  作者：Michał Michalak、Paweł Czerwiński、Katarzyna Śniady‐Maciążek、Szymon Musioł、Oksana Danylyuk、Michał Wierzbicki、Michele Tomasini、Albert Poater

  DOI：10.1002/chem.202303241

  日期：2024.3

  of chiral NHC−Au−Cl complexes, bearing sterically encumbered NHC ligands, has been accessed by merging anilines with commercially available chiral aminoalcohols and amines. Evaluation of the catalytic activity in enantioselective allenol cyclization has pointed out the importance of the steric hindrance and conformational flexibility of the NHC core for reactivity. Ion metathesis between NHC−Au−Cl

  位阻但活跃：通过将苯胺与市售手性氨基醇和胺合并，获得了一个新的手性 NHC−Au−Cl 配合物家族，带有位阻 NHC 配体。对映选择性二烯醇环化催化活性的评估指出了 NHC 核心的空间位阻和构象灵活性对于反应活性的重要性。与 DCM 相比，金络合物活化所需的 NHC−Au−Cl 和 AgOT 之间的离子复分解在常用的 MeNO 2中似乎非常缓慢。
• Enantioselective C–H Functionalization–Addition Sequence Delivers Densely Substituted 3-Azabicyclo[3.1.0]hexanes
  作者：Julia Pedroni、Nicolai Cramer

  DOI：10.1021/jacs.7b07024

  日期：2017.9.13

  An enantioselective C–H functionalization route to perfluoroalkyl-containing 3-azabicyclo[3.1.0]hexanes is disclosed. A modular and bench-stable diazaphospholane ligand enables highly enantioselective Pd(0)-catalyzed cyclopropane C–H functionalization using trifluoroacetimidoyl chlorides as electrophilic partners. In turn, the resulting cyclic ketimine products react smoothly with a broad variety of

  公开了对含全氟烷基的3-氮杂双环[3.1.0]己烷的对映选择性CH官能团化方法。模块化且稳定的二氮杂膦烷配体可使用三氟乙酰亚胺基氯化物作为亲电伙伴，实现高度对映选择性的Pd（0）催化的环丙烷C–H功能化。反过来，生成的环状酮亚胺产物与多种亲核试剂以一锅法平稳反应，从而能够快速，模块化地构建重取代的吡咯烷。
• Preparation of enantiomers of 1-(1-naphthyl)-2,2-dimethylpropylamine and their behaviour as chiral solvating agents: study of diastereochemic association by Job's plots and intermolecular NOE measurements
  作者：A Port、A Virgili、A Alvarez-Larena、J.F Piniella

  DOI：10.1016/s0957-4166(00)00334-7

  日期：2000.9

  Enantiomers of 1-(1-naphthyl)-2,2-dimethylpropylamine have been obtained and considered as chiral solvating agents against several compounds. The formed complexes have been studied with the aid of the nuclear Overhauser effect and its stoichiometry by the method of continuous variations. Two diastereoisomeric complexes present similar geometry of association by pi-pi -stacking of the aromatic rings and by hydrogen bonding of the functional groups. (C) 2000 Elsevier Science Ltd. All rights reserved.