(R,R)-N-(1-indanyl)-1-phenylethylamine | 221179-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (R,R)-N-(1-indanyl)-1-phenylethylamine
• 英文别名: N-1-indan-(1-phenylethyl)amine；(1R)-N-[(1R)-1-phenylethyl]-2,3-dihydro-1H-inden-1-amine
• CAS: 221179-27-7
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: VGYGBIBUJVQRBO-CXAGYDPISA-N

物化性质

• 沸点：
  360.4±21.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (R,R)-N-(1-indanyl)-1-phenylethylamine 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、405.3 kPa 条件下， 反应 62.0h， 生成 (R)-(-)-1-氨基茚满
  参考文献：
  名称：

  α-氨基取代的苯并环化合物的不对称合成中的立体和区域选择性

  摘要：

  对映体纯的手性胺benzocyclic 6 - 8分别用对应的前手性酮的不对称氨基转移获得9A - Ç。该方法涉及：（a）由前手性酮9a - c和廉价的手性助剂（R）-或（S）-苯乙胺（PEA）形成手性亚胺10a - c；（b）不对称地诱导这些亚胺还原为非对映异构胺11a – c和12a – c; （c）催化氢化以除去手性PEA助剂的苄基片段。亚胺还原的立体选择性以及催化氢化的区域选择性在很大程度上取决于与苯环缩合的饱和环的尺寸。该方法用于开发一种方便，高产且立体选择性的途径，以制备几种实用上重要的旋光性α-氨基取代的苯并环化合物。

  DOI：

  10.1016/s0957-4166(98)00467-4
• 作为产物：
  描述：

  N-(α-methylbenzyl)indanimine 在 N-(9-脱氧-epi-辛克宁-9-基)氮苯酰胺 、 三氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以96%的产率得到
  参考文献：
  名称：

  A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin

  摘要：

  The diastereoselective, trichlorosilane-mediate reduction of imines, bearing different and removable chiral auxiliaries, in combination either with achiral bases or catalytic amounts of chiral Lewis bases, was investigated to afford immediate precursors of chiral APIs (Active Pharmaceutical Ingredients). The carbon-nitrogen double bond reduction was successfully performed in batch and in flow mode, in high yields and almost complete stereocontrol. By this metal-free approach, the formal synthesis of rasagiline and tamsulosin was successfully accomplished in micro(meso) flow reactors, under continuous flow conditions. The results of these explorative studies represent a new, important step towards the development of automated processes for the preparation of enantiopure biologically active compounds. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.01.023

文献信息

• Direct Reductive Amination from Ketones, Aldehydes to Synthesize Amines Using N, S-Dual Doped Co/C Catalyst
  作者：Hongwei Zhang、Ying Liu、Ling Zhang、Xiong Wang、He Sun、Chengyu Liu、Jinxing Ye、Ruihua Cheng

  DOI：10.1007/s10562-021-03911-2

  日期：2022.12

  As a key intermediate in natural products and pharmaceutics, N-(R, R)-phenethyl-1-indane was directly prepared by one-pot reductive amination of 1-indanone and R-( +)-α-phenethylamine using abundant molecular hydrogen as a reductant. Compared with the traditional noble metal catalyst, the Co-VB1(1:2)/C-900 catalysts showed higher selectivity in this reaction, and generated the N-(R, R)-phenethyl-1-indane

  N -( R , R )-phenethyl-1-indane作为天然产物和医药的关键中间体，利用丰富的分子氢，通过一锅还原胺化 1-茚满酮和R -( +)-α-苯乙胺直接制备N -( R , R )-phenethyl-1-indane作为还原剂。与传统贵金属催化剂相比，Co-VB 1 (1:2)/C-900催化剂在该反应中表现出更高的选择性，并以高收率生成N- ( R , R )-苯乙基-1-茚满。Co-VB 1 (1:2)/C-900 催化剂是通过盐酸硫胺素 (VB 1 ) 的改性制备的) 作为氮源和硫源。同时，催化剂可多次重复使用。N -( R , R )-苯乙基-1-茚满的合成具有成本效益和原子经济性。该催化剂还在一系列底物（从醛或酮）的还原胺化中表现出中等至良好的催化活性，以提供各种有价值的化合物。 图形概要
• A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin
  作者：Davide Brenna、Margherita Pirola、Laura Raimondi、Anthony J. Burke、Maurizio Benaglia

  DOI：10.1016/j.bmc.2017.01.023

  日期：2017.12

  The diastereoselective, trichlorosilane-mediate reduction of imines, bearing different and removable chiral auxiliaries, in combination either with achiral bases or catalytic amounts of chiral Lewis bases, was investigated to afford immediate precursors of chiral APIs (Active Pharmaceutical Ingredients). The carbon-nitrogen double bond reduction was successfully performed in batch and in flow mode, in high yields and almost complete stereocontrol. By this metal-free approach, the formal synthesis of rasagiline and tamsulosin was successfully accomplished in micro(meso) flow reactors, under continuous flow conditions. The results of these explorative studies represent a new, important step towards the development of automated processes for the preparation of enantiopure biologically active compounds. (C) 2017 Elsevier Ltd. All rights reserved.
• Stereo- and regioselectivity in asymmetric synthesis of α-amino substituted benzocyclic compounds
  作者：Arie L. Gutman、Marina Etinger、Gennady Nisnevich、Felix Polyak

  DOI：10.1016/s0957-4166(98)00467-4

  日期：1998.12

  The enantiomerically pure chiral benzocyclic amines 6–8 were obtained by asymmetric transamination of the corresponding prochiral ketones 9a–c. The method involves: (a) formation of chiral imines 10a–c from the prochiral ketones 9a–c and the inexpensive chiral auxiliary (R)- or (S)-phenylethylamine (PEA); (b) asymmetrically induced reduction of these imines to the diastereomeric amines 11a–c and 12a–c;

  对映体纯的手性胺benzocyclic 6 - 8分别用对应的前手性酮的不对称氨基转移获得9A - Ç。该方法涉及：（a）由前手性酮9a - c和廉价的手性助剂（R）-或（S）-苯乙胺（PEA）形成手性亚胺10a - c；（b）不对称地诱导这些亚胺还原为非对映异构胺11a – c和12a – c; （c）催化氢化以除去手性PEA助剂的苄基片段。亚胺还原的立体选择性以及催化氢化的区域选择性在很大程度上取决于与苯环缩合的饱和环的尺寸。该方法用于开发一种方便，高产且立体选择性的途径，以制备几种实用上重要的旋光性α-氨基取代的苯并环化合物。