(1S,2S)-2-(phenylamino)cycloheptan-1-ol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,2S)-2-(phenylamino)cycloheptan-1-ol
• 英文别名: (1S,2S)-2-anilinocycloheptan-1-ol
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: YTRMKCUMKDZJGH-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R,7S)-cycloheptene oxide 、 苯胺 在 C₁₄H₂₂N₂O₂S 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 以91%的产率得到(1S,2S)-2-(phenylamino)cycloheptan-1-ol
  参考文献：
  名称：

  Unravelling a New Class of Chiral Organocatalyst for Asymmetric Ring-Opening Reaction of Meso Epoxides with Anilines

  摘要：

  Chiral sulfinamide based organocatalyst 11 was synthesized from readily available starting materials and used for the asymmetric ring-opening (ARO) reaction of meso epoxides with anilines. A high yield (up to 95%) of chiral beta-amino alcohols with excellent enantioselectivity (ee up to 99%) was achieved in 24-30 h at rt under optimized reaction conditions. A probable mechanism for the catalytic ARO reaction is envisaged by H-1 and C-13 NMR experiments.

  DOI：

  10.1021/ol500699c

文献信息

• Vanadium-Salan Catalyzed Enantioselective Ring Opening of <i>meso</i>-Epoxides with Aromatic Amines
  作者：Jiangtao Sun、Chengjian Zhu、Zhenya Dai、Minghua Yang、Xu Pan

  DOI：10.1055/s-2008-1067109

  日期：——

  The first example of enantioselective ring-opening of meso-epoxides catalyzed by chiral oxovanadium(V)-salan complexes is reported. The reaction furnished 1,2-aminoalcohols in good yields and moderate to high enantioselectivities (up to 87%).

  报道了手性氧钒(V)-salan 配合物催化内消旋环氧化物的对映选择性开环的第一个例子。该反应以良好的收率和中等至高的对映选择性（高达 87%）提供了 1,2-氨基醇。
• Solvent-free aminolysis of aliphatic and aryloxy epoxides with sulfated zirconia as solid acid catalyst
  作者：Arpan K. Shah、Manish Kumar、Sayed H.R. Abdi、Rukhsana I. Kureshy、Noor-ul H. Khan、Hari C. Bajaj

  DOI：10.1016/j.apcata.2014.08.024

  日期：2014.9

  Single-step and two-steps synthetic procedure for the synthesis of sulfated zirconia (SZ) was developed, which were calcined at 500, 600 and 700 degrees C and characterized by various physico-chemical methods such as PXRD, FTIR, surface area, microanalysis, NH3-TPD and DRIFT analysis. These SZ materials were then employed as solid acid catalysts for the aminolysis of different aliphatic/aromatic terminal, aryloxy and meso epoxides with aromatic and aliphatic amines under ambient conditions. Amongst the catalyst prepared, SZ-2-600 prepared in two-steps and 600 degrees C calcined was found to be the most efficient catalyst to give beta-amino alcohols in up to 98% yield and >99% regioselectivity. The SZ catalyst was successfully recycled and reused up to six catalytic runs with intact efficiency. (C) 2014 Elsevier B.V. All rights reserved.
• An Efficient Method for Cleavage of Epoxides with Aromatic Amines
  作者：Govindasamy Sekar、Vinod K. Singh

  DOI：10.1021/jo981196c

  日期：1999.1.1
• Facile Ring Opening of Oxiranes with Aromatic Amines in Fluoro Alcohols
  作者：Udayan Das、Benoit Crousse、Venkitasamy Kesavan、Danièle Bonnet-Delpon、Jean-Pierre Bégué

  DOI：10.1021/jo000031c

  日期：2000.10.1
• Enantiomerically pure N-aryl-β-amino alcohols by enzymatic resolution
  作者：Govindasamy Sekar、Rajesh M Kamble、Vinod K Singh

  DOI：10.1016/s0957-4166(99)00401-2

  日期：1999.9

  N-Aryl-beta-amino acetates, obtained by opening epoxides with aromatic amines followed by acetylation of the hydroxyl group, were resolved using crude pig liver esterase (PLE) enzyme in DMSO in high enantiomeric excess. (C) 1999 Elsevier Science Ltd. All rights reserved.