3-Propionyl-(4S)-ethyl-1,3-thiazolidine-2-thione | 102831-91-4

• 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-(4S)-ethyl-1,3-thiazolidine-2-thione
• 英文别名: 3-propionyl-4(S)-ethyl-1,3-thiazolidine-2-thione；1-[(4S)-4-ethyl-2-sulfanylidene-1,3-thiazolidin-3-yl]propan-1-one
• CAS: 102831-91-4
• 化学式: C₈H₁₃NOS₂
• 分子量: 203.329
• InChiKey: RFHMRUKFIHKLBK-LURJTMIESA-N

物化性质

• 沸点：
  286.9±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)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 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：

  3-Propionyl-(4S)-ethyl-1,3-thiazolidine-2-thione 在 N-乙基哌啶 、 tin(II) trifluoromethanesulfonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 (4S)-1-(tert-Butyldimethylsilyl)-4-<(1R)-1-<((4S)-4-ethyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one
  参考文献：
  名称：

  .beta.-Lactams. 1. Highly diastereoselective alkylation of 4-acetoxyazetidin-2-one useful for 1.beta.-methylcarbapenem synthesis

  摘要：

  On the basis of the principle of hard and soft acids and bases, a highly diastereoselective ''asymmetric soft acid-soft base imine alkylation'' was developed. 4-Acetoxyazetidin-2-one (5) was alkylated with the tin(II) enolates of 3-acyl-(4S)-ethyl(and isopropyl)-1,3-thiazolidine-2-thiones 7a,b and 21a,b. The resultant alkylation products (9a,b and 24a,b) could be converted to 17, the key intermediate for the syntheses of both thienamycin (2) and imipenem (3), and to 35, the key intermediate for the synthesis of 1-beta-methylcarbapenem.

  DOI：

  10.1021/jo00041a031

文献信息

• Azetidin-2-one derivatives and process for production thereof
  申请人：LEDERLE (JAPAN) LTD.

  公开号：EP0213610A1

  公开（公告）日：1987-03-11

  An azetidin-2-one derivative represented by the following formula (I) wherein R' represents a hydrogen atom, a lower alkyl group, an aryl group, an aralkyl group, a lower alkoxy group, aralkoxy group, a lower alkylthio group, an aralkylthio group, or a substituted amino group, R2 represents a hydrogen atom, a lower alkyl group, an aryl group or an aralkyl group, and R3 represents a hydrogen atom or a group of the formula In which R4 represents a hydrogen atom or a protective group for the hydroxyl group; and a process for production thereof.

  由下式（I）代表的氮杂环丁烷-2-酮衍生物 其中 R'代表氢原子、低级烷基、芳基、烷基、低级烷氧基、烷氧基、低级烷硫基、烷硫基或取代的氨基，R2 代表氢原子、低级烷基、芳基或烷基，R3 代表氢原子或下式中的基团。 其中 R4 代表氢原子或羟基的保护基团；及其生产工艺。
• .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.
• Highly diastereoselective alkylation onto 4-acetoxy-2-azetidinones employing tin(II) enolates of 3-acyl C-4-chiral 1,3-thiazolidine-2-thiones
  作者：Yoshimitsu. Nagao、Toshio. Kumagai、Satoshi. Tamai、Takao. Abe、Yasuhiro. Kuramoto、Tooru. Taga、Sakae. Aoyagi、Yunosuke. Nagase、Masahito. Ochiai、. et al.

  DOI：10.1021/ja00275a082

  日期：1986.7
• NAGAO, JOSIMITSU;KUMAGAYA, TOSIO;TAMAI, CATOPY;KYPAMOTO, YASUXIRO;SIMIDZU+
  作者：NAGAO, JOSIMITSU、KUMAGAYA, TOSIO、TAMAI, CATOPY、KYPAMOTO, YASUXIRO、SIMIDZU+

  DOI：——

  日期：——
• MATSUNAGA, XIROSI;TAMAI, SATORU;KOBAYASI, SIGEHAKI;KUMAGAYA, TOSIO;NAGASE+
  作者：MATSUNAGA, XIROSI、TAMAI, SATORU、KOBAYASI, SIGEHAKI、KUMAGAYA, TOSIO、NAGASE+

  DOI：——

  日期：——