(S)-N-(4-chlorobenzyl)-1-phenylethanamine

• 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: (S)-N-(4-chlorobenzyl)-1-phenylethanamine
• 英文别名: (S)-N-(4-chlorobenzyl)-1-phenylethylamine；(1S)-N-[(4-chlorophenyl)methyl]-1-phenylethanamine
• 化学式: C₁₅H₁₆ClN
• 分子量: 245.752
• InChiKey: OQLCAYPQNQXBKW-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-N-(4-chlorobenzyl)-1-phenylethanamine 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S,S)-N,N'-bis-(4-chlorobenzyl) N,N'-bis-(1-phenylethyl)-ethane-1,2-diamine
  参考文献：
  名称：

  Facile Synthesis of (S,S)‐1,2‐Diacylamides and (S,S)‐1,2‐Diamines with C ₂‐Symmetry

  摘要：

  A series of chiral vicinal tertiary diacylamides with C-2-symmetry was synthesized from (S)-alpha-phenylethylamine, different aromatic aldehydes, and oxalyl chloride. The diacylamides obtained were then reduced to afford chiral vicinal diamines with C-2-symmetry. We propose that the diacylamides existed in four stable conformational isomers in solution because of the dihedral angle between acylamide bonds.

  DOI：

  10.1080/00397910600770698
• 作为产物：
  描述：

  [1-(4-Chloro-phenyl)-meth-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine 在 sodium tetrahydroborate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.0h， 生成 (S)-N-(4-chlorobenzyl)-1-phenylethanamine
  参考文献：
  名称：

  Facile Synthesis of (S,S)‐1,2‐Diacylamides and (S,S)‐1,2‐Diamines with C ₂‐Symmetry

  摘要：

  A series of chiral vicinal tertiary diacylamides with C-2-symmetry was synthesized from (S)-alpha-phenylethylamine, different aromatic aldehydes, and oxalyl chloride. The diacylamides obtained were then reduced to afford chiral vicinal diamines with C-2-symmetry. We propose that the diacylamides existed in four stable conformational isomers in solution because of the dihedral angle between acylamide bonds.

  DOI：

  10.1080/00397910600770698

文献信息

• Asymmetric organocatalytic reduction of ketimines with catecholborane employing a N-triflyl phosphoramide Brønsted acid as catalyst
  作者：Dieter Enders、Andreas Rembiak、Matthias Seppelt

  DOI：10.1016/j.tetlet.2012.11.055

  日期：2013.2

  The first asymmetric reduction of ketimines with catecholborane employing an enantiopure N-triflyl phosphoramide as the organocatalyst has been developed. Five mole % of the catalyst provides the corresponding secondary amines in very good to almost quantitative yields and good enantioselectivities up to 86:14 e.r. under mild reaction conditions.

  已经开发了使用对映体纯的N-三氟乙磷酰胺作为有机催化剂用儿茶酚硼烷对酮亚胺进行的第一次不对称还原。在温和的反应条件下，五摩尔％的催化剂可提供非常好的至几乎定量的产率和高达86:14 er的良好对映选择性的相应仲胺。
• 1,2,3-Triazole-boranes: stable and efficient reagents for ketone and aldehyde reductive amination in organic solvents or in water
  作者：Wenyan Liao、Yunfeng Chen、Yuxiu Liu、Haifeng Duan、Jeffrey L. Petersen、Xiaodong Shi

  DOI：10.1039/b915361f

  日期：——

  Air, moisture and thermally stable 1,2,3-triazole-borane complexes were developed as new practical reagents for ketone/aldehyde amination with high efficiency and excellent substrate diversity.

  空气，水分和热稳定的1,2,3-三唑-硼烷配合物被开发为高效/高效的酮/醛胺化的新型实用试剂，并且具有出色的底物多样性。
• Application of Monodentate Secondary Phosphine Oxides, a New Class of Chiral Ligands, in Ir(I)-Catalyzed Asymmetric Imine Hydrogenation
  作者：Xiao-bin Jiang、Adriaan J. Minnaard、Bart Hessen、Ben L. Feringa、Alexander L. L. Duchateau、Jean G. O. Andrien、Jeroen A. F. Boogers、Johannes G. de Vries

  DOI：10.1021/ol034282u

  日期：2003.5.1

  Secondary phosphine oxides were prepared from R(1)PCl(2) and R(2)MgBr, followed by hydrolysis. They were obtained in an enantiopure form by preparative chiral HPLC. These new monodentate ligands were tested in the iridium-catalyzed hydrogenation of imines at 25 bar. Enantioselectivities up to 76% were obtained at L/Ir = 2. Addition of pyridine (Pyr/Ir = 1:2) raised the ee to 83%. Using pyridine as

  由R（1）PC1（2）和R（2）MgBr制备仲氧化膦，然后水解。它们通过制备手性HPLC以对映体纯形式获得。这些新的单齿配体在25 bar的铱催化的亚胺氢化中进行了测试。在L / Ir = 2时，对映选择性高达76％。吡啶的加入（Pyr / Ir = 1：2）使ee升至83％。使用吡啶作为添加剂允许将L / Ir比降低至1而不会降低ee。[反应：看文字]
• METHOD FOR PRODUCING OPTICALLY ACTIVE VINYLCYCLOPROPANECARBOXYLIC ACID DERIVATIVE AND OPTICALLY ACTIVE VINYLCYCLOPROPANEAMINO ACID DERIVATIVE
  申请人：Tanaka Tatsuyoshi

  公开号：US20110245529A1

  公开（公告）日：2011-10-06

  The objective of the present invention is to provide a method for obtaining an optically active vinylcyclopropanecarboxylic acid derivative with high yield and high optical purity using a safe material available at low cost. In addition, the objective of the present invention is to provide a method for safely-obtaining an optically active vinylcyclopropaneamino acid with high optical purity at low cost. The problems can be solved by a method for obtaining an optically active vinylcyclopropanecarboxylic acid derivative, which method contains the step of reacting a racemic vinylcyclopropanecarboxylic acid derivative with an optically active amine compound, to obtain a diastereomer salt of optically active vinylcyclopropanecarboxylic acid derivative-amine compound. In addition, it is possible to obtain a vinylcyclopropaneamino acid by deriving the vinylcyclopropaneamino acid from thus obtained diastereomer salt of optically active vinylcyclopropanecarboxylic acid derivative-amine compound.

  本发明的目的是提供一种方法，使用成本低廉的安全材料高产高光学纯度地获得光学活性的乙烯基环丙烷羧酸衍生物。此外，本发明的目的还是提供一种以低成本安全地获得高光学纯度的光学活性乙烯基环丙烷氨基酸的方法。这些问题可以通过一种方法来解决，该方法包含将外消旋的乙烯基环丙烷羧酸衍生物与光学活性胺化合物反应，以获得光学活性乙烯基环丙烷羧酸衍生物-胺化合物的对映异构体盐。此外，可以通过从所获得的光学活性乙烯基环丙烷羧酸衍生物-胺化合物的对映异构体盐中推导出乙烯基环丙烷氨基酸。
• OPTICALLY ACTIVE VINYL-CYCLOPROPANE CARBOXYLIC ACID DERIVATIVE AND OPTICALLY ACTIVE VINYL-CYCLOPROPANE AMINO ACID DERIVATIVE MANUFACTURING METHOD
  申请人：Kaneka Corporation

  公开号：EP2345633A1

  公开（公告）日：2011-07-20

  The objective of the present invention is to provide a method for obtaining an optically active vinylcyclopropanecarboxylic acid derivative with high yield and high optical purity using a safe material available at low cost. In addition, the objective of the present invention is to provide a method for safely-obtaining an optically active vinylcyclopropaneamino acid with high optical purity at low cost. The problems can be solved by a method for obtaining an optically active vinylcyclopropanecarboxylic acid derivative, which method contains the step of reacting a racemic vinylcyclopropanecarboxylic acid derivative with an optically active amine compound, to obtain a diastereomer salt of optically active vinylcyclopropanecarboxylic acid derivative - amine compound. In addition, it is possible to obtain a vinylcyclopropaneamino acid by deriving the vinylcyclopropaneamino acid from thus obtained diastereomer salt of optically active vinylcyclopropanecarboxylic acid derivative - amine compound.

  本发明的目的是提供一种利用低成本安全材料获得高产率和高光学纯度的光学活性乙烯基环丙烷羧酸衍生物的方法。此外，本发明的目的是提供一种以低成本安全地获得光学活性高光学纯度的乙烯基环丙烷氨基 酸的方法。这些问题可以通过一种获得光学活性乙烯基环丙烷羧酸衍生物的方法来解决，该方法包含以下步骤：将外消旋乙烯基环丙烷羧酸衍生物与光学活性胺化合物反应，得到光学活性乙烯基环丙烷羧酸衍生物-胺化合物的非对映异构盐。此外，还可以从这样得到的光学活性乙烯基环丙烷羧酸衍生物-胺化合物的非对映异构盐中得到乙烯基环丙烷氨基酸。