(3R,4S)-3-tert-butyldimethylsiloxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one | 880781-88-4

• 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: (3R,4S)-3-tert-butyldimethylsiloxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one
• 英文别名: (3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one
• CAS: 880781-88-4
• 化学式: C₂₂H₂₉NO₃Si
• 分子量: 383.563
• InChiKey: IXYAMJFITQTSRP-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-tert-butyldimethylsiloxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one 在 ammonium cerium(IV) nitrate 、 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.25h， 生成 (3R,4S)-3-羟基-4-苯基-2-氮杂环丁酮
  参考文献：
  名称：

  Asymmetric synthesis of 3-amino-2-hydroxyalkanoates by Mannich reaction of menthyl acetate with imines and subsequent oxidation

  摘要：

  Lithium amide-assisted Mannich-type reaction of menthyl acetate-derived lithium enolate with PMP-arylaldimines and subsequent in situ oxidation with oxaziridine gave syn-3-amino-3-aryl-2-hydroxypropanoates with high syn-selectivity and diastereoselectivity (with respect to menthyl moiety) in a one-pot procedure. Propargyl aldehyde-derived imines were also stereoselectively converted to the Mannich-oxidation products by a stepwise procedure. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.05.031
• 作为产物：
  描述：

  4-methoxy-N-[(E)-phenylmethylidene]aniline 在 咪唑 、 甲基溴化镁 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (3R,4S)-3-tert-butyldimethylsiloxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of 3-amino-2-hydroxyalkanoates by Mannich reaction of menthyl acetate with imines and subsequent oxidation

  摘要：

  Lithium amide-assisted Mannich-type reaction of menthyl acetate-derived lithium enolate with PMP-arylaldimines and subsequent in situ oxidation with oxaziridine gave syn-3-amino-3-aryl-2-hydroxypropanoates with high syn-selectivity and diastereoselectivity (with respect to menthyl moiety) in a one-pot procedure. Propargyl aldehyde-derived imines were also stereoselectively converted to the Mannich-oxidation products by a stepwise procedure. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.05.031

文献信息

• Asymmetric synthesis of 3-amino-2-hydroxyalkanoates by Mannich reaction of menthyl acetate with imines and subsequent oxidation
  作者：Seiji Hata、Kiyoshi Tomioka

  DOI：10.1016/j.tet.2007.05.031

  日期：2007.8

  Lithium amide-assisted Mannich-type reaction of menthyl acetate-derived lithium enolate with PMP-arylaldimines and subsequent in situ oxidation with oxaziridine gave syn-3-amino-3-aryl-2-hydroxypropanoates with high syn-selectivity and diastereoselectivity (with respect to menthyl moiety) in a one-pot procedure. Propargyl aldehyde-derived imines were also stereoselectively converted to the Mannich-oxidation products by a stepwise procedure. (c) 2007 Published by Elsevier Ltd.