trans-1-Propyl-3-acetyl-4-phenyl-2-azetidinone | 88121-68-0

• 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: trans-1-Propyl-3-acetyl-4-phenyl-2-azetidinone
• 英文别名: (3R,4R)-3-acetyl-4-phenyl-1-propylazetidin-2-one
• CAS: 88121-68-0
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: MNOTVMTVBVHKQN-STQMWFEESA-N

物化性质

• 沸点：
  400.3±45.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-benzylidene-propylamine 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 cobalt acetylacetonate 苯硅烷 、 氧气 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 25.0~70.0 ℃ 、2.94 MPa 条件下， 反应 8.0h， 生成 trans-1-Propyl-3-acetyl-4-phenyl-2-azetidinone
  参考文献：
  名称：

  Palladium-Catalyzed Carbonylative [2 + 2] Cycloaddition for the Stereoselective Synthesis of Either cis- or trans-3-Alkenyl .beta.-Lactams

  摘要：

  A new potential alkenylketene equivalent, prepared without use of a carboxylic acid or an activated derivative, has been exploited. Palladium-catalyzed carbonylation of an allyl phosphate in the presence of an imine and a tertiary amine under CO pressure (30 kg cm(-2)) stereoselectively gave either a cis-or trans-3-alkenyl beta-lactam in high yield. The stereochemical outcome strongly depends on the nature of the imine employed. Imines conjugated with a carbonyl such as a ketone or an ester stereoselectively produce cis-beta-lactams at room temperature, whereas imines unconjugated with a carbonyl group exclusively afford trans-beta-lactams at 70 degrees C.

  DOI：

  10.1021/jo00090a023

文献信息

• Yamamoto, Yutaka; Watanabe, Yokiyoshi, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 5, p. 1871 - 1879
  作者：Yamamoto, Yutaka、Watanabe, Yokiyoshi

  DOI：——

  日期：——
• Masayuki, Sato; Ogasawara, Hiromichi; Yoshizumi, Eriko, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 6, p. 1902 - 1909
  作者：Masayuki, Sato、Ogasawara, Hiromichi、Yoshizumi, Eriko、Kato, Tetsuzo

  DOI：——

  日期：——
• SATO, MASAYUKI;OGASAWARA, HIROMICHI;YOSHIZUMI, ERIKO;KATO, TETSUZO, CHEM. AND PHARM. BULL., 1983, 31, N 6, 1902-1909
  作者：SATO, MASAYUKI、OGASAWARA, HIROMICHI、YOSHIZUMI, ERIKO、KATO, TETSUZO

  DOI：——

  日期：——
• Palladium-Catalyzed Carbonylative [2 + 2] Cycloaddition for the Stereoselective Synthesis of Either cis- or trans-3-Alkenyl .beta.-Lactams
  作者：Hideo Tanaka、A. K. M. Abdul Hai、Masahiro Sadakane、Hiroshi Okumoto、Sigeru Torii

  DOI：10.1021/jo00090a023

  日期：1994.6

  A new potential alkenylketene equivalent, prepared without use of a carboxylic acid or an activated derivative, has been exploited. Palladium-catalyzed carbonylation of an allyl phosphate in the presence of an imine and a tertiary amine under CO pressure (30 kg cm(-2)) stereoselectively gave either a cis-or trans-3-alkenyl beta-lactam in high yield. The stereochemical outcome strongly depends on the nature of the imine employed. Imines conjugated with a carbonyl such as a ketone or an ester stereoselectively produce cis-beta-lactams at room temperature, whereas imines unconjugated with a carbonyl group exclusively afford trans-beta-lactams at 70 degrees C.