(2R,3R)-2-phenethyl-3-vinylaziridine | 203398-09-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,3R)-2-phenethyl-3-vinylaziridine
• 英文别名: (2R,3R)-2-ethenyl-3-(2-phenylethyl)aziridine
• CAS: 203398-09-8
• 化学式: C₁₂H₁₅N
• 分子量: 173.258
• InChiKey: CIDTZYLEJXDICC-VXGBXAGGSA-N

物化性质

• 沸点：
  263.5±9.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-phenethyl-3-vinylaziridine 在 高氯酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (4R,5S)-4-phenethyl-5-vinyloxazolidin-2-one
  参考文献：
  名称：

  A Regio- and Stereodivergent Route to All Isomers of vic-Amino Alcohols

  摘要：

  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.

  DOI：

  10.1021/jo0262053
• 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 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 117.92h， 生成 (2R,3R)-2-phenethyl-3-vinylaziridine
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Aza-[3,3]-Claisen Enolate Rearrangement in Vinylaziridines: Stereoselective Synthesis of Mono-, Di-, and Trisubstituted Seven-Membered Lactams
  作者：Ulf M. Lindström、Peter Somfai

  DOI：10.1002/1521-3765(20010105)7:1<94::aid-chem94>3.0.co;2-m

  日期：2001.1.5

  and subjected to LiHMDS in THF at -78 degrees C. Upon warming to room temperature, the resulting amide enolates underwent a highly stereoselective [3,3]-sigmatropic rearrangement to give mono-, di-, and trisubstituted seven-membered lactams in good yields. The scope and limitations of the process have been investigated by using variously substituted vinylaziridines. A kinetically controlled process proceeding

  几种2,3-二取代的乙烯基氮丙啶已被N-酰化，并在-78℃下于THF中进行LiHMDS处理。升温至室温后，所得酰胺烯酸酯进行高度立体选择性[3,3]-σ重排，得到单- ，二和三取代的七元内酰胺，收率高。通过使用各种取代的乙烯基氮丙啶已研究了该方法的范围和局限性。通过六元舟状过渡态组装进行的动力学控制过程已被用来解释反应的立体化学结果。
• 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
• 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.