(S)-1-phenyl-N-((S)-1-(4-(fluoro)phenyl)ethyl)ethan-1-amine | 444643-11-2

• 物质功能分类: 有机原料 - 氨基化合物
• 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)-1-phenyl-N-((S)-1-(4-(fluoro)phenyl)ethyl)ethan-1-amine
• 英文别名: (S)-1-(4-fluorophenyl)-N-((S)-1-phenylethyl)ethan-1-amine；(1S)-N-[(1S)-1-(4-fluorophenyl)ethyl]-1-phenylethanamine
• CAS: 444643-11-2
• 化学式: C₁₆H₁₈FN
• 分子量: 243.324
• InChiKey: VUKXJACOTHKDES-STQMWFEESA-N

物化性质

• 沸点：
  317.2±22.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-phenyl-N-((S)-1-(4-(fluoro)phenyl)ethyl)ethan-1-amine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 60.0 ℃ 、500.0 kPa 条件下， 反应 12.0h， 以98%的产率得到(S)-(-)-1-(4-氟苯基)乙胺
  参考文献：
  名称：

  通过延迟苄位氢解裂解实际合成光学活性氟取代的 α-苯乙胺

  摘要：

  在芳环上具有氟原子的双（α-甲基苄基）胺氢解中的高区域选择性是由于氟-亚基苄基位置处氢解裂解的延迟...

  DOI：

  10.1246/cl.2004.1424
• 作为产物：
  描述：

  4-氟苯乙酮 在 zinc(II) chloride sodium tetrahydroborate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 27.0h， 生成 (S)-1-phenyl-N-((S)-1-(4-(fluoro)phenyl)ethyl)ethan-1-amine
  参考文献：
  名称：

  通过延迟苄位氢解裂解实际合成光学活性氟取代的 α-苯乙胺

  摘要：

  在芳环上具有氟原子的双（α-甲基苄基）胺氢解中的高区域选择性是由于氟-亚基苄基位置处氢解裂解的延迟...

  DOI：

  10.1246/cl.2004.1424

文献信息

• B(C₆F₅)₃-Catalyzed Asymmetric Reductive Amination of Ketones with Ammonia Borane
  作者：Zhentao Pan、Leixin Shen、Dingguo Song、Zhen Xie、Fei Ling、Weihui Zhong

  DOI：10.1021/acs.joc.8b01362

  日期：2018.10.5

  first example of metal-free B(C6F5)3-catalyzed asymmetric reduction amination of ketones with chiral α-methylbenzylamine (α-MBA) using ammonia borane as the reductant is reported. This one-pot method has a broad substrate scope and provides various chiral amines in 81–95% yield with 80–99% de. This protocol was further applied in the total synthesis of cinacalcet.

  报道了使用氨硼烷作为还原剂，用手性α-甲基苄胺（α-MBA）进行的无金属的B（C 6 F 5）3催化的酮的不对称还原胺化的第一个实例。这种一锅法具有广泛的底物范围，并以81-95％的收率和80-99％的de提供了各种手性胺。该方案进一步应用于西那卡塞的全合成中。
• Process for producing optically active 1-(fluoro- or trifluoromethyl-substituted phenyl) ethylamine and process for purifying same
  申请人：Central Glass Company, Limited

  公开号：US06797842B2

  公开（公告）日：2004-09-28

  An optically active 1-(fluoro- or trifluoromethyl-substituted phenyl)ethylamine is produced with high optical purity and in an industrially simple and efficient manner by asymmetrically reducing an optically active imine, obtained by dehydration and condensation of a fluoro- or trifluoromethyl-substituted phenylmethyl ketone and an optically active primary amine under acidic conditions, using a hydride reducing agent to convert to an optically active secondary amine, and subjecting the secondary amine or its salt of an inorganic acid or organic acid to hydrogenolysis. In addition, an optically active 1-(fluoro- or trifluoromethyl-substituted phenyl)ethylamine is purified to an even higher optical purity in an industrially simple and efficient manner by converting the optically active secondary amine of the synthetic intermediate obtained by asymmetric reduction, or an optically active 1-(3,5-bis-trifluoromethylphenyl)ethylamine, one of the target compounds, to an inorganic or organic acid salt followed by recrystallization purification. This ethylamine is an important intermediate of pharmaceuticals and agricultural chemicals.

  通过在酸性条件下将氟代或三氟甲基取代的苯甲基酮和光学活性的初级胺脱水和缩合得到的光学活性亚胺，再使用氢化还原剂将其转化为光学活性的二级胺，然后将这个二级胺或其无机酸或有机酸盐进行氢解，可以以高光学纯度和在工业上简单高效的方式生产光学活性的1-(氟代或三氟甲基取代的苯基)乙胺。此外，通过将通过不对称还原得到的合成中间体的光学活性二级胺，或目标化合物之一的光学活性1-(3,5-双三氟甲基苯基)乙胺转化为无机或有机酸盐，然后进行重结晶纯化，可以以工业上简单高效的方式将光学活性的1-(氟代或三氟甲基取代的苯基)乙胺提纯至更高的光学纯度。这种乙胺是制药和农药化学品的重要中间体。
• [EN] OPTICALLY ACTIVE 1-(FLUORO-,TRIFLUOROMETHYL-OR TRIFLUOROMETHOXY-SUBSTITUTED PHENYL)ALKYLAMINE N-MONOALKYL DERIVATIVES AND PROCESS FOR PRODUCING SAME<br/>[FR] DERIVES DE 1-( PHENYLE A SUBSTITUTION FLUORO,TRIFLUOROMETHYLE OU TRIFLUOROMETHOXY)ALKYLAMINE N-MONOALKYLE OPTIQUEMENT ACTIFS ET LEUR PROCEDE DE PRODUCTION
  申请人：CENTRAL GLASS CO LTD

  公开号：WO2004022521A1

  公开（公告）日：2004-03-18

  An optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy-substituted phenyl)alkylamine N-monoalkyl derivative represented by the formula [4] is produced by a process including (a) reacting an optically active secondary amine, represented by the formula [1], with an alkylation agent R2-X, in the presence of a base, thereby converting the secondary amine into an optically active tertiary amine represented by the formula [3]; and (b) subjecting the tertiary amine to a hydrogenolysis, thereby producing the N-monoalkyl derivative,wherein R represents a fluorine atom, trifluoromethyl group or trifluoromethoxy group, n represents an integer of from 1 to 5, each of R1 and R2 independently represents an alkyl group having a carbon atom number of from 1 to 6, Me represents a methyl group, Ar represents a phenyl group or 1- or 2-naphthyl group, * represents a chiral carbon, and X represents a leaving group.

  通过以下过程制备一种光学活性的1-(氟代、三氟甲基或三氟甲氧基取代的苯基)烷基胺N-单烷基衍生物，其化学式如下[4]：(a) 用碱存在下，将光学活性的二级胺（化学式[1]表示）与烷基化剂R2-X反应，从而将二级胺转化为光学活性的三级胺（化学式[3]表示）；(b) 将三级胺进行氢解作用，从而生成N-单烷基衍生物，其中R代表氟原子、三氟甲基基团或三氟甲氧基团，n代表1至5之间的整数，R1和R2分别代表具有1至6个碳原子的烷基基团，Me代表甲基基团，Ar代表苯基或1-或2-萘基，*代表一个手性碳，X代表一个离去基团。
• A Bifunctional MOF Catalyst Containing Metal–Phosphine and Lewis Acidic Active Sites
  作者：Ram R. R. Prasad、Daniel M. Dawson、Paul A. Cox、Sharon E. Ashbrook、Paul A. Wright、Matthew L. Clarke

  DOI：10.1002/chem.201803094

  日期：2018.10.12

  Post‐synthetic modification of the hafnium metal–organic framework MOF‐808(Hf) to include triarylphosphine ligands is reported. Sulfonated phenylphosphines are incorporated without oxidation to give a “MOF ligand” that can complex late transition metals such as Ir and Rh to give a bifunctional catalyst containing both metal–phosphine complexes and the Lewis acidic framework hafnium metal sites. The

  据报道金属有机骨架MOF-808（Hf）的合成后修饰包括三芳基膦配体。掺入的磺化苯基膦无需氧化即可生成“ MOF配体”，该配体可以与后期过渡金属（例如Ir和Rh）络合，从而生成同时包含金属-膦络合物和路易斯酸性骨架ha金属位点的双功能催化剂。含金属化膦的MOF充当串联还原胺化和氢氨甲基化反应的完全非均相双功能催化剂。
• Optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy- substituted phenyl)alkylamine N-monoalkyl derivatives and process for producing same
  申请人：Ishii Akihiro

  公开号：US20070142670A1

  公开（公告）日：2007-06-21

  An optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy-substituted phenyl)alkylamine N-monoalkyl derivative represented by the formula 4 is produced by a process including (a) reacting an optically active secondary amine, represented by the formula 1, with an alkylation agent R 2 —X, in the presence of a base, thereby converting the secondary amine into an optically active tertiary amine represented by the formula 3; and (b) subjecting the tertiary amine to a hydrogenolysis, thereby producing the N-monoalkyl derivative, wherein R represents a fluorine atom, trifluoromethyl group or trifluoromethoxy group, n represents an integer of from 1 to 5, each of R 1 and R 2 independently represents an alkyl group having a carbon atom number of from 1 to 6, Me represents a methyl group, Ar represents a phenyl group or 1- or 2-naphthyl group, * represents a chiral carbon, and X represents a leaving group.