N-(tosyloxy)-3-phthalimido-2-azetidinone | 152402-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(tosyloxy)-3-phthalimido-2-azetidinone
• CAS: 152402-70-5
• 化学式: C₁₈H₁₄N₂O₆S
• 分子量: 386.385
• InChiKey: OFMXBTVYCJYXBM-UHFFFAOYSA-N

物化性质

• 沸点：
  563.3±60.0 °C(predicted)
• 密度：
  1.61±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  101.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(tosyloxy)-3-phthalimido-2-azetidinone 在 叠氮基三甲基硅烷 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 17.0h， 以60%的产率得到3-azido-3-phthalimido-2-azetidinone
  参考文献：
  名称：

  Diastereoselective addition of nucleophiles to the C3 position of N-(tosyloxy)-.beta.-lactams

  摘要：

  trans-3-Substituted-beta-lactams 22a-j are conveniently synthesized by treating 21 with suitable nucleophiles in the presence of Et3N or (i-Pr)2EtN. The key aspects of this method relative to traditional methods are that the C3 position of beta-lactam 21 acts as an electrophilic center and the addition of nucleophiles is accompanied by N-O bond cleavage. The reaction is tolerant of a variety of alkyl groups at the C4 position, although an electron-withdrawing group at C4 is detrimental. The rate of reaction is increased if an electron-withdrawing group is present at the C3 position. Base-initiated enolization followed by an S(N)2' displacement of tosylate by a nucleophile is mechanistically consistent with these observations, but enolization is considered to be the rate-determining step. Suitable sources of nucleophiles are TMSX, Et3NH.X, or (i-Pr)2EtNH.X, while Bu4N.X or LiX initiates the formation of a byproduct, 31. Triethylamine has been found to act as a competitive nucleophile to form 30 and therefore was not the preferred base for the reaction. The yield of product can bc optimized by using a non-nucleophilic base, such as (i-Pr)2EtN, and an excess of nucleophile.

  DOI：

  10.1021/ja00055a026
• 作为产物：
  描述：

  N-phthalimido-D,L-serine 在 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 N-(tosyloxy)-3-phthalimido-2-azetidinone
  参考文献：
  名称：

  Diastereoselective addition of nucleophiles to the C3 position of N-(tosyloxy)-.beta.-lactams

  摘要：

  trans-3-Substituted-beta-lactams 22a-j are conveniently synthesized by treating 21 with suitable nucleophiles in the presence of Et3N or (i-Pr)2EtN. The key aspects of this method relative to traditional methods are that the C3 position of beta-lactam 21 acts as an electrophilic center and the addition of nucleophiles is accompanied by N-O bond cleavage. The reaction is tolerant of a variety of alkyl groups at the C4 position, although an electron-withdrawing group at C4 is detrimental. The rate of reaction is increased if an electron-withdrawing group is present at the C3 position. Base-initiated enolization followed by an S(N)2' displacement of tosylate by a nucleophile is mechanistically consistent with these observations, but enolization is considered to be the rate-determining step. Suitable sources of nucleophiles are TMSX, Et3NH.X, or (i-Pr)2EtNH.X, while Bu4N.X or LiX initiates the formation of a byproduct, 31. Triethylamine has been found to act as a competitive nucleophile to form 30 and therefore was not the preferred base for the reaction. The yield of product can bc optimized by using a non-nucleophilic base, such as (i-Pr)2EtN, and an excess of nucleophile.

  DOI：

  10.1021/ja00055a026