(4S)-3-acetyl-4-ethyl-1,3-thiazolidine-2-thione | 101979-44-6

• 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: (4S)-3-acetyl-4-ethyl-1,3-thiazolidine-2-thione
• 英文别名: 3-acetyl-4(S)-ethyl-1,3-thiazolidine-2-thione；3-Acetyl 4S-Ethyl-1,3-thiazolidine-2-thione；1-[(4S)-4-ethyl-2-sulfanylidene-1,3-thiazolidin-3-yl]ethanone
• CAS: 101979-44-6
• 化学式: C₇H₁₁NOS₂
• 分子量: 189.302
• InChiKey: UTBHJZOXMQMTNK-LURJTMIESA-N

物化性质

• 熔点：
  41 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  270.2±23.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (4S)-3-acetyl-4-ethyl-1,3-thiazolidine-2-thione 生成 (3S,4R)-3-<(1S)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-(carboxymethyl)azetidin-2-one
  参考文献：
  名称：

  NAGAO, JOSIMITSU;KUMAGAYA, TOSIO;KURAMOTO, YASUXIRO

  摘要：

  DOI：
• 作为产物：
  描述：

  (4S)-Ethyl-1,3-thiazolidine-2-thione 、 乙酰氯 生成 (4S)-3-acetyl-4-ethyl-1,3-thiazolidine-2-thione
  参考文献：
  名称：

  NAGAO, JOSIMITSU;FUDZITA, EHJITI;XAGIVARA, YUITI;KUMAGAYA, TOSIO

  摘要：

  DOI：

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。
• New C-4-chiral 1,3-thiazolidine-2-thiones: excellent chiral auxiliaries for highly diastereo-controlled aldol-type reactions of acetic acid and .alpha.,.beta.-unsaturated aldehydes
  作者：Yoshimitsu Nagao、Yuichi Hagiwara、Toshio Kumagai、Masahito Ochiai、Takehisa Inoue、Keiji Hashimoto、Eiichi Fujita

  DOI：10.1021/jo00362a047

  日期：1986.6
• .beta.-Lactams. 2. Diastereoselective alkylative discrimination of racemic 3-substituted 4-acetoxyazetidin-2-ones and its application to the synthesis of a chiral key intermediate for carbapenem syntheses
  作者：Yoshimitsu Nagao、Yunosuke Nagase、Toshio Kumagai、Yasuhiro Kuramoto、Shigeaki Kobayashi、Yoshinori Inoue、Tooru Taga、Hirokazu Ikeda

  DOI：10.1021/jo00041a032

  日期：1992.7

  Alkylation of rac 3-substituted 4-acetoxyazetidin-2-one 4 with chiral tin(II) enolate 8 derived from 3-acetyl-(4S)-ethyl-1,3-thiazolidine-2-thione (ETT) (7) proceeded in a highly diastereoselective manner to give alkylated products 9, 10, and 11 in 42%, 20%, and 9% yields, respectively, after chromatographic purification. Similar alkylation of rac-5 with 8 gave 16, 17, and 18 in 45%, 29%, and 5% yields, respectively. Compound 9 was readily converted to 33, a chiral key intermediate for the synthesis of carbapenems. Analytical separation of rac-4 was effectively done with an HPLC technique employing a chiral column packed with A(S)MBC.
• .beta.-Lactams. 1. Highly diastereoselective alkylation of 4-acetoxyazetidin-2-one useful for 1.beta.-methylcarbapenem synthesis
  作者：Yoshimitsu Nagao、Toshio Kumagai、Yunosuke Nagase、Satoshi Tamai、Yoshinori Inoue、Motoo Shiro

  DOI：10.1021/jo00041a031

  日期：1992.7

  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.
• Matsunaga, Hiroshi; Kumagai, Toshio; Inoue, Yoshinori, Heterocycles, 1994, vol. 39, # 2, p. 859 - 866
  作者：Matsunaga, Hiroshi、Kumagai, Toshio、Inoue, Yoshinori、Nagao, Yoshimitsu

  DOI：——

  日期：——