3-Propionyl-4,4-dimethyl-1,3-thiazolidine-2-thione | 115026-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-Propionyl-4,4-dimethyl-1,3-thiazolidine-2-thione
• 英文别名: 1-(4,4-Dimethyl-2-sulfanylidene-1,3-thiazolidin-3-yl)propan-1-one
• CAS: 115026-46-5
• 化学式: C₈H₁₃NOS₂
• 分子量: 203.329
• InChiKey: VJDFQYIQHAPQEX-UHFFFAOYSA-N

物化性质

• 沸点：
  272.7±23.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-乙酰氧基氮杂环丁酮 、 3-Propionyl-4,4-dimethyl-1,3-thiazolidine-2-thione 在 N-乙基哌啶 、 tin(II) trifluoromethanesulfonate 作用下， 以80%的产率得到(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<(2-thioxo-4,4-dimethyl-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one
  参考文献：
  名称：

  .beta.-Lactams. 3. Asymmetric total synthesis of new non-natural 1.beta.-methylcarbapenems exhibiting strong antimicrobial activities and stability against human renal dehydropeptidase-I

  摘要：

  Asymmetric synthesis of 11, the precursor to chiral (3R,4R)-3-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-4-acetoxyazetidin-2-one (3) was achieved by utilizing a highly diastereoselective aldol-type reaction of acetaldehyde and the chiral tin(II) enolate of 5. Similar diastereoselective alkylations of chiral and achiral tin(II) enolates 13a-d with chiral 3 were also performed to obtain the desired alkylated azetidin-2-ones (17a-d). Compounds 17a,b were successfully converted to new, non-natural 1-beta-methylcarbapenems 1a and 1b, which exhibited strong and wide-ranging antimicrobial activities and excellent stability against human renal dehydropeptidase-I.

  DOI：

  10.1021/jo00041a033

文献信息

• Simple and highly diastereoselective synthesis of a 1β-methylcarbapenem key intermediate involving divalent tin enolates
  作者：Robert Déziel、Denis Favreau

  DOI：10.1016/s0040-4039(00)85301-0

  日期：——

  A simple and diastereoselective synthesis of 1β-methylcarbapenem key intermediate has been accomplished via a novel CC bond formation at the C-4 position of 4-acetoxyazetidinone involving divalent tin enolates of 3-propanoyl thiazolidine and oxazolidine-2-thiones derivatives.

  通过在4-乙酰氧基氮杂环丁酮的C-4位上形成新颖的CC键，涉及3-丙酰基噻唑烷和恶唑烷-2-硫酮衍生物的二价烯醇锡，可以简单且非对映选择性地合成1β-甲基卡巴培南关键中间体。
• PROCESS FOR PRODUCING 4-SUBSTITUTED AZETIDINONE DERIVATIVE
  申请人：NIPPON SODA CO., LTD.

  公开号：EP0573667B1

  公开（公告）日：2001-06-13
• US5731431A
  申请人：——

  公开号：US5731431A

  公开（公告）日：1998-03-24
• .beta.-Lactams. 3. Asymmetric total synthesis of new non-natural 1.beta.-methylcarbapenems exhibiting strong antimicrobial activities and stability against human renal dehydropeptidase-I
  作者：Yoshimitsu Nagao、Yunosuke Nagase、Toshio Kumagai、Hiroshi Matsunaga、Takao Abe、Osamu Shimada、Takaaki Hayashi、Yoshinori Inoue

  DOI：10.1021/jo00041a033

  日期：1992.7

  Asymmetric synthesis of 11, the precursor to chiral (3R,4R)-3-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-4-acetoxyazetidin-2-one (3) was achieved by utilizing a highly diastereoselective aldol-type reaction of acetaldehyde and the chiral tin(II) enolate of 5. Similar diastereoselective alkylations of chiral and achiral tin(II) enolates 13a-d with chiral 3 were also performed to obtain the desired alkylated azetidin-2-ones (17a-d). Compounds 17a,b were successfully converted to new, non-natural 1-beta-methylcarbapenems 1a and 1b, which exhibited strong and wide-ranging antimicrobial activities and excellent stability against human renal dehydropeptidase-I.