(R)-2-(Methyl-phenyl-amino)-2-phenyl-ethanol | 219813-92-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-2-(Methyl-phenyl-amino)-2-phenyl-ethanol
• 英文别名: (R)-2-(methyl(phenyl)amino)-2-phenylethan-1-ol
• CAS: 219813-92-0
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: JPELDYHXMRRIBT-HNNXBMFYSA-N

物化性质

• 沸点：
  378.325±35.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.120±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  23.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-2-(Methyl-phenyl-amino)-2-phenyl-ethanol 在 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.08h， 生成 (2R)-2-(N-methylanilino)-2-phenylethanethiol
  参考文献：
  名称：

  Concepts for ligand design in asymmetric catalysis: a study of chiral amino thiol ligands

  摘要：

  A series of new chiral sulfur-nitrogen chelate ligands, derived from amino acids, has been synthesised rationally. Fruitless experiments into catalytic asymmetric conjugate additions and desymmetrisation of meso-epoxides led us to analyse our ligands in the catalytic asymmetric addition of diethylzinc to aromatic aldehydes. These latter experiments were successful with chiral benzylic alcohols being obtained in up to 82% enantiomeric excess. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00344-9
• 作为产物：
  描述：

  triphenylbismuth(V) diacetate 在 lithium aluminium tetrahydride 、 copper diacetate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.55h， 生成 (R)-2-(Methyl-phenyl-amino)-2-phenyl-ethanol
  参考文献：
  名称：

  Concepts for ligand design in asymmetric catalysis: a study of chiral amino thiol ligands

  摘要：

  A series of new chiral sulfur-nitrogen chelate ligands, derived from amino acids, has been synthesised rationally. Fruitless experiments into catalytic asymmetric conjugate additions and desymmetrisation of meso-epoxides led us to analyse our ligands in the catalytic asymmetric addition of diethylzinc to aromatic aldehydes. These latter experiments were successful with chiral benzylic alcohols being obtained in up to 82% enantiomeric excess. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00344-9

文献信息

• Kinetic resolution of <i>N</i>-aryl β-amino alcohols <i>via</i> asymmetric aminations of anilines
  作者：Zheng Guo、Jinglei Xie、Tao Hu、Yunrong Chen、Houchao Tao、Xiaoyu Yang

  DOI：10.1039/d1cc03117a

  日期：——

  An efficient kinetic resolution of N-aryl β-amino alcohols has been developed via asymmetric para-aminations of anilines with azodicarboxylates enabled by chiral phosphoric acid catalysis. Broad substrate scope and high kinetic resolution performances were afforded with this method. Control experiments supported the critical roles of the NH and OH group in these reactions.

  的有效动力学拆分ñ -芳基β氨基醇已经开发经由非对称段苯胺-aminations与偶氮二羧酸盐能够通过手性磷酸催化。这种方法提供了广泛的底物范围和高动力学分辨率性能。对照实验支持 NH 和 OH 基团在这些反应中的关键作用。
• CsPbBr₃ perovskite quantum dots as a visible light photocatalyst for cyclisation of diamines and amino alcohols: an efficient approach to synthesize imidazolidines, fused-imidazolidines and oxazolidines
  作者：Bikram Gurung、Sajan Pradhan、Debesh Sharma、Deshaj Bhujel、Siddhant Basel、Shivanand Chettri、Sagarmani Rasaily、Anand Pariyar、Sudarsan Tamang

  DOI：10.1039/d2cy00799a

  日期：——

  photocatalysts using dibromoisocyanuric acid (DBI) as a benign non-toxic bromide precursor. The QDs were applied as a visible light photocatalyst for intramolecular cyclisation of diamines and amino alcohols to obtain a range of enantiopure bioactive heterocycles such as imidazolidines, fused-imidazolidines and 1,3-oxazolidines in high yields (isolated yield up to 82%, ee >99%). The reaction is simple

  我们报告了使用二溴异氰尿酸 (DBI) 作为良性无毒溴化物前体合成高度稳定的 CsPbBr 3 QD基光催化剂。量子点被用作可见光光催化剂，用于二胺和氨基醇的分子内环化，以高产率获得一系列对映纯生物活性杂环，如咪唑烷、稠合咪唑烷和 1,3-恶唑烷（分离产率高达 82%，ee >99%）。该反应简单，在室温下露天进行，可扩展。量子点表现出高 TON (177) 和催化效率（与传统制备的 CsPbBr 3 量子点相比，催化效率快三倍））。反应的表观量子效率 (AQE) 接近于统一 ( φ = 0.96 在 460 nm 和φ = 0.98 在 436 nm)。
• Concepts for ligand design in asymmetric catalysis: a study of chiral amino thiol ligands
  作者：James C. Anderson、Rachel Cubbon、Michael Harding、Daniel S. James

  DOI：10.1016/s0957-4166(98)00344-9

  日期：1998.10

  A series of new chiral sulfur-nitrogen chelate ligands, derived from amino acids, has been synthesised rationally. Fruitless experiments into catalytic asymmetric conjugate additions and desymmetrisation of meso-epoxides led us to analyse our ligands in the catalytic asymmetric addition of diethylzinc to aromatic aldehydes. These latter experiments were successful with chiral benzylic alcohols being obtained in up to 82% enantiomeric excess. (C) 1998 Elsevier Science Ltd. All rights reserved.