(1R,2S)-2-amino-1-d-indane | 193756-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1R,2S)-2-amino-1-d-indane
• CAS: 193756-59-1
• 化学式: C₉H₁₁N
• 分子量: 134.185
• InChiKey: LMHHFZAXSANGGM-ZPHNWTDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  26.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-甲基-双(三氟乙酰胺) 、 (1R,2S)-2-amino-1-d-indane 以 乙酸乙酯 为溶剂， 以89%的产率得到(1R,2S)-2-trifluoroacetamido-1-d-indane
  参考文献：
  名称：

  Enantioselective Synthesis of cis- and trans-2(S)-Amino-1-d-indane:  Debrominative [1,2]-Hydride Shift Rearrangement by Reduction of cis-2-Azido-1-bromoindane with LiAlD₄

  摘要：

  This article describes the synthesis of the racemic and optically pure forms of (1R,2S)-cis- and (1S,2S)-trans-2-Amino-1-d-indanes 2 {94% ee} and 3 {83% ee} (ee determined by H-2 NMR in chiral liquid crystal PBLG/CH2Cl2, Courtieu, J. et al. J. Am. Chem. Soc. 1995, 117, 6520) prepared by LiAlD4 reduction of (+/-)- and (1S,2S)-trans-2-azido-1-bromomoindane (11) {87% ee} and (+/-) and (1R,2S)-cis-2-azido-1-[(methanesulfonyl)oxy]indane (10) {83% ee}, respectively. Whereas the LiAlD4 reduction of trans-2-azido-1-bromomoindane (11) led to cis-2-amino-1-d-indane 2 by a S(N)2 pathway, exclusively, the reduction of cis-1-bromo derivative 12 gave only small amounts of the S(N)2 product trans-2-amino-1-d-indane (3) (15%) accompanied by 2-amino-2-d-indane (4) (85%) in which the deuterium atom is incorporated in alpha position to the amino group. It was established that the primary amine 4 comes from a stereospecific [1,2]-hydride shift rearrangement, We propose that the azido group is reduced first, and the [1,2]-hydride shift rearrangement prevails over the competitive S(N)2 substitution. The exclusive formation of trans-2-amino-1-d-indane (3) requires cis-2-azido-1-[(methanesulfonyl)oxy]indane (10) where the mesylate assisted by electrophilic Li+ cation switches the deuteride attack to the ester carbon and the direct S(N)2 substitution occurs before the azide is reduced.

  DOI：

  10.1021/jo970378o
• 作为产物：
  描述：

  2-azido-1-bromo-2,3-dihydro-1H-indene 在 lithium aluminium deuteride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(1R,2S)-2-amino-1-d-indane
  参考文献：
  名称：

  Enantioselective Synthesis of cis- and trans-2(S)-Amino-1-d-indane:  Debrominative [1,2]-Hydride Shift Rearrangement by Reduction of cis-2-Azido-1-bromoindane with LiAlD₄

  摘要：

  This article describes the synthesis of the racemic and optically pure forms of (1R,2S)-cis- and (1S,2S)-trans-2-Amino-1-d-indanes 2 {94% ee} and 3 {83% ee} (ee determined by H-2 NMR in chiral liquid crystal PBLG/CH2Cl2, Courtieu, J. et al. J. Am. Chem. Soc. 1995, 117, 6520) prepared by LiAlD4 reduction of (+/-)- and (1S,2S)-trans-2-azido-1-bromomoindane (11) {87% ee} and (+/-) and (1R,2S)-cis-2-azido-1-[(methanesulfonyl)oxy]indane (10) {83% ee}, respectively. Whereas the LiAlD4 reduction of trans-2-azido-1-bromomoindane (11) led to cis-2-amino-1-d-indane 2 by a S(N)2 pathway, exclusively, the reduction of cis-1-bromo derivative 12 gave only small amounts of the S(N)2 product trans-2-amino-1-d-indane (3) (15%) accompanied by 2-amino-2-d-indane (4) (85%) in which the deuterium atom is incorporated in alpha position to the amino group. It was established that the primary amine 4 comes from a stereospecific [1,2]-hydride shift rearrangement, We propose that the azido group is reduced first, and the [1,2]-hydride shift rearrangement prevails over the competitive S(N)2 substitution. The exclusive formation of trans-2-amino-1-d-indane (3) requires cis-2-azido-1-[(methanesulfonyl)oxy]indane (10) where the mesylate assisted by electrophilic Li+ cation switches the deuteride attack to the ester carbon and the direct S(N)2 substitution occurs before the azide is reduced.

  DOI：

  10.1021/jo970378o

文献信息

• Enzymatic Hydroxylation by Dopamine β‐Hydroxylase
  作者：Anton A. Mitrochkine、Frank Eydoux、Gérard Gil、Marius Réglier

  DOI：10.1002/(sici)1099-0690(199806)1998:6<1171::aid-ejoc1171>3.0.co;2-#

  日期：1998.6

  three-dimensional aspects of the chemistry of dopamine β-hydroxylase (DBH) was studied through a conformationally-restricted substrate analog approach. We found that the DBH-catalyzed hydroxylation of 2-aminoindane (1) exclusively produced the trans-(1S,2S)-2-amino-1-indanol (4S) (93% ee) in contrast to the stereochemical course of the pro-R hydroxylation of the DBH/phenethylamine reaction. Studies with

  通过构象受限的底物类似物方法研究了多巴胺β-羟化酶（DBH）化学的三维方面。我们发现，DBH催化的2-氨基茚满（1）的羟化反应只产生反式-（1 S，2 S）-2-氨基-1-茚满醇（4S）（93％ee），而立体化学过程则相反。的亲- - [R的DBH /苯乙胺反应的羟基化。立体定向氘标记的2-氨基茚满2和3的研究表明（1 S）-氨基茚满醇4S的产生是立体定向pro - S夺氢，然后结合氧并保持整体构型的结果。基于这些发现，我们提出了苯乙胺底物与酶相互作用的模型。