(4R,αS)-N(1)-(α-methylbenzyl)-4-phenylazetidin-2-one | 78075-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (4R,αS)-N(1)-(α-methylbenzyl)-4-phenylazetidin-2-one
• 英文别名: N-[(S)-α-methylbenzyl]-4(R)-phenylazetidin-2-one；N-((S)-α-Phenylethyl)-4(R)-phenylazetidin-2-one；(4R)-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one
• CAS: 78075-71-5
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: ABKPBDQKMBOBLP-XJKSGUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (S)-(-)-N-苄基-1-苯基-乙胺 在 正丁基锂 、 氯化亚砜 、 ammonium cerium (IV) nitrate 、 甲基溴化镁 、 水 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 乙腈 为溶剂， 反应 23.0h， 生成 (4R,αS)-N(1)-(α-methylbenzyl)-4-phenylazetidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of syn- and anti-α-deuterio-β3-phenylalanine derivatives

  摘要：

  The conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of aryl substituted tert-butyl cinnamate esters followed by reaction of the resultant lithium beta-amino enolates with D2O provides access to anti configured alpha-deuterio-beta-aminocinnamate esters in high dr. The corresponding syn configured diastereoisomers were also obtained with high diastereoselectivity via the conjugate addition of lithium (5)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of tert-butyl alpha-deuteriocinnamate esters followed by reaction of the resultant lithium beta-amino enolates with 2-pyridone. After deprotection both the syn- and anti-diastereoisomers of the corresponding alpha-deuterio-beta(3)-amino acids can be isolated in high dr. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.008

文献信息

• Lithium (α-methylbenzyl)allylamide: a differentially protected chiral ammonia equivalent for the asymmetric synthesis of β-amino acids and β-lactams
  作者：Stephen G. Davies、David R. Fenwick

  DOI：10.1039/c39950001109

  日期：——

  The addition products from the highly stereoselective conjugate additions of lithium (αS)-(α-methylbenzyl)allylamide to α, β-unsaturated tert-butyl esters are efficiently deallylated with tris(triphenylphosphine)rhodium(I) chloride and converted, after transesterification to the methyl esters and cyclisation with methylmagnesium bromide, to the corresponding homochiral N-(α-methylbenzyl)-4-substituted-azetidm-2-ones

  由（αS）-（α-甲基苄基）烯丙基酰胺高度立体选择性共轭加成至α，β-不饱和叔丁酯的加成产物可有效地与三（三苯基膦）铑（I）氯化物脱酯并在酯交换反应后转化生成甲基酯，并用甲基溴化镁环化，生成相应的手性N-（α-甲基苄基）-4-取代的氮杂环丁烷-2-酮。
• Diastereoface-differentiating synthesis of substituted .beta.-lactams from chiral imines and/or chiral .alpha.-chloro iminium chlorides
  作者：Ewa Rogalska、Czeslaw Belzecki

  DOI：10.1021/jo00182a015

  日期：1984.4
• Solvent-free stereoselective synthesis of β-aryl-β-amino acid esters by the Rodionov reaction using microwave irradiation
  作者：Nelly N. Romanova、Alexander G. Gravis、Pavel V. Kudan、Yuri G. Bundel’

  DOI：10.1070/mc2001v011n01abeh001360

  日期：2001.1
• ROGALSKA, E.;BELZECKI, C., J. ORG. CHEM., 1984, 49, N 8, 1397-1402
  作者：ROGALSKA, E.、BELZECKI, C.

  DOI：——

  日期：——