(3S,4R)-4-amino-1-phenylhex-5-en-3-ol | 203397-90-4

• 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: (3S,4R)-4-amino-1-phenylhex-5-en-3-ol
• CAS: 203397-90-4
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: QTHMFVZSWQLVNJ-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-amino-1-phenylhex-5-en-3-ol 在 4-二甲氨基吡啶 、 三乙胺 、 三苯基膦 、 lithium hexamethyldisilazane 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2H-吖庚英-2-酮,1,3,4,7-四氢-7-(2-苯基乙基)-,(7R)-
  参考文献：
  名称：

  A Highly Stereoselective Aza-[3,3]-Claisen Rearrangement of Vinylaziridines as a Novel Entry to Seven-Membered Lactams

  摘要：

  DOI：

  10.1021/ja971572v
• 作为产物：
  描述：

  trans-2,3-epoxy-5-phenylpentan-1-ol 在 草酰氯 、 氨 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 反应 99.92h， 生成 (3S,4R)-4-amino-1-phenylhex-5-en-3-ol
  参考文献：
  名称：

  Lindstroem, Ulf M.; Somfai, Peter, Synthesis, 1998, # 1, p. 109 - 117

  摘要：

  DOI：

文献信息

• A Regio- and Stereodivergent Route to All Isomers of <i>v</i><i>ic</i>-Amino Alcohols
  作者：Berit Olofsson、Peter Somfai

  DOI：10.1021/jo0262053

  日期：2002.11.1

  Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.
• A Regio- and Stereodivergent Synthesis of <i>v</i><i>ic</i>-Amino Alcohols
  作者：Berit Olofsson、Uttam Khamrai、Peter Somfai

  DOI：10.1021/ol006736i

  日期：2000.12.1

  [GRAPHICS]A regio- and stereodivergent synthesis of vic-amino alcohols starting from vinylepoxides is described. The developed strategy focuses on the propensity of vinylepoxides and vinylaziridines to be ring-opened at the allylic position by suitable nucleophiles and makes use of reactions that perform such tasks selectively with either retention or inversion of configuration.
• Synthesis of N–H vinylaziridines: a comparative study
  作者：Berit Olofsson、Roel Wijtmans、Peter Somfai

  DOI：10.1016/s0040-4020(02)00610-5

  日期：2002.7

  Vinylaziridines are useful and versatile synthetic intermediates, as the relief of ring-strain provides a driving force for efficient ring-opening or ring-expansion reactions. Furthermore, the vinyl group can be derivatized into interesting functionalities. The ring-closure of vicinal amino alcohols constitutes a straightforward route to aziridines. Several methods exist for this transformation, although many cannot be applied to vinylaziridines due to their acid lability. This comparative study describes the most effective sequences for the formation of N-H vinylaziridines. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Lindstroem, Ulf M.; Somfai, Peter, Synthesis, 1998, # 1, p. 109 - 117
  作者：Lindstroem, Ulf M.、Somfai, Peter

  DOI：——

  日期：——
• A Highly Stereoselective Aza-[3,3]-Claisen Rearrangement of Vinylaziridines as a Novel Entry to Seven-Membered Lactams
  作者：Ulf M. Lindström、Peter Somfai

  DOI：10.1021/ja971572v

  日期：1997.9.1