(E)-2-(2-oxopropylidene)thiazolidine | 126979-03-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: (E)-2-(2-oxopropylidene)thiazolidine
• 英文别名: 2-acetonylidene-1,3-thiazolidine；1-(E)-thiazolidin-2-ylidene-propan-2-one；1-(4,5-dihydro-thiazol-2-yl)-propan-2-one；2-Acetyl-methylen-thiazolidin；2-Propanone, 1-(2-thiazolidinylidene)-, (E)-(9CI)；(1E)-1-(1,3-thiazolidin-2-ylidene)propan-2-one
• CAS: 126979-03-1
• 化学式: C₆H₉NOS
• 分子量: 143.21
• InChiKey: YWTKURIRFABBEI-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-oxopropylidene)thiazolidine 在 劳森试剂 作用下， 以 苯 为溶剂， 反应 4.0h， 以85%的产率得到2-thioacetylmethylenethiazolidine
  参考文献：
  名称：

  Conformational preferences of α-functionalised keten-S,N-acetals: Potential role of SO and SS interactions in solution

  摘要：

  PMR spectra of carbonyl compounds 2a-k reveal significant variations in the population off and Z Isomers on changing the solvent from CDCl3 to DMSO-d(6). In non-polar media, the intramolecular N-H....O hydrogen bonded form is exclusively observed. In DMSO-d(6), the alternative Z form is also populated. A similar conformational switch is also noted in the corresponding thiones. Different interpretations are critically analysed. The most consistent explanation is suggested to involvean interplay of N-H....X hydrogen bonding and S...X attractive interaction (X=0,S) in these systems. Ah initio calculations support this interpretation.

  DOI：

  10.1016/0040-4020(94)01023-s
• 作为产物：
  描述：

  2-thiazolidinylideneacetylacetone 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以97%的产率得到(E)-2-(2-oxopropylidene)thiazolidine
  参考文献：
  名称：

  Synthesis of Heterocyclic KeteneN,S-Acetals and Their Reactions with Esters of α,β-Unsaturated Acids

  摘要：

  烯酮 S,S-乙醛 2 与 2-氨基-1-乙硫醇反应，生成取代的 2-亚甲基噻唑烷 3。光谱数据证实了这些产物的结构为烯酮 N,S-乙醛。化合物 3a-f 与 δ,δ-不饱和酸的酯反应，通过亲电加成和环缩合顺序，得到噻唑并[3,2-a] 吡啶-5-酮衍生物 4、6 和 7。

  DOI：

  10.1055/s-1990-26822

文献信息

• Wang, He-Ting; Wang, Xiao-Jun; Huang, Zhi-Tang, Chemische Berichte, 1990, vol. 123, # 11, p. 2141 - 2145
  作者：Wang, He-Ting、Wang, Xiao-Jun、Huang, Zhi-Tang

  DOI：——

  日期：——
• Determination of the Chemical Structure of the Intense Roasty, Popcorn-like Odorant 5-Acetyl-2,3-dihydro-1,4-thiazine
  作者：Thomas Hofmann、Rainer Haessner、Peter Schieberle

  DOI：10.1021/jf00056a043

  日期：1995.8

  The chemical structure of a novel intense popcorn-like odorant isolated from the reaction of cysteine and ribose was studied by one- and two-dimensional NMR spectroscopy and high-resolution mass spectrometry, and the structure elucidation was confirmed by synthetic experiments. Thus, the odorant was identified as 5-acetyl-2,3-dihydro-1,4-thiazine (ADT). A sensory study including 5-propionyl- (PDT) and 5-butanoyl-2,3-dihydro-1,4-thiazine (BDT) revealed that also PDT and BDT elicited roasty, popcorn-like odors. However, the odor threshold of the BDT was by a factor of 50 000 higher than those of ADT and PDT (0.06 and 0.1 ng/L of air, respectively).
• Spitzner,R. et al., Journal fur praktische Chemie (Leipzig 1954), 1976, vol. 318, p. 298 - 312
  作者：Spitzner,R. et al.

  DOI：——

  日期：——
• GUPTA, AKHILESH K.;CHAKRASALI, R. T.;HA, H.;JUNJAPPA, H., SYNTHESIS,(1989) N, C. 141-142
  作者：GUPTA, AKHILESH K.、CHAKRASALI, R. T.、HA, H.、JUNJAPPA, H.

  DOI：——

  日期：——
• SPITZNER R.; DILL G.; SCHROTH W.; HENNIG H.; JAMIL K. M., J. PRAKT. CHEM. <JPCE-AO>, 1976, 318, NO 2, 298-312
  作者：SPITZNER R.、 DILL G.、 SCHROTH W.、 HENNIG H.、 JAMIL K. M.

  DOI：——

  日期：——