5-苯基噻唑烷-2-硫酮 | 1437-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5-苯基噻唑烷-2-硫酮
• 英文名称: 5-phenylthiazolidine-2-thione
• 英文别名: 5-phenyl-thiazolidine-2-thione；5-Phenyl-1,3-thiazolidin-2-thion；2-Mercapto-5-phenyl-thiazolin；5-Phenyl-thiazolidin-2-thion；5-Phenyl-thiothiazolidon-(2)；5-Phenylthiazolidin-2-thion；5-phenyl-1,3-thiazolidine-2-thione
• CAS: 1437-98-5
• 化学式: C₉H₉NS₂
• 分子量: 195.309
• InChiKey: OCZUTEPGPZTEOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-苯基噻唑烷-2-硫酮 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-N-(4-chlorophenyl)-5-phenyl-2-thioxothiazolidine-3-carboxamide
  参考文献：
  名称：

  Synthesis and Fungicidal Activity of Simple Structural 1,3-Thiazolidine-2-Thione Derivatives

  摘要：

  A series of simple structural 1,3-thiazolidine-2-thione derivatives with various substituents on the S-, N-, 4-, and 5-positions was synthesized with high yields from various vicinal amino alcohols via two steps and screened for their antifungal activity. Bioassay results reveal that some thiazolidine-2-thione derivatives show strong antifungal activities against P. capsici, G. zeae, S. sclerotiorum, A. alternata, B. cinerea, or R. solani. The SAR analysis indicates that N-acyl substituted and 4-alkyl substituents can enhance the antifungal activity. Notably, 4-isopropyl-N-propionylthiazoldine-2-thione shows excellent activity against B. cinerea and G. zeae with IC50 values at 3.7 mu g/mL and 6.5 mu g/mL, respectively, and 4-isobutyl-N-propionylthiazoldine-2-thione shows remarkable fungicidal activity against R. solani, S. sclerotiorum, and G. zeae with IC50 values at 1.0 mu g/mL, 12.1 mu g/mL, and 11.0 mu g/mL, respectively.

  DOI：

  10.1080/10426507.2014.931399
• 作为产物：
  描述：

  2-氨基-1-苯乙醇 在 sodium hydroxide 、 硫酸 作用下， 生成 5-苯基噻唑烷-2-硫酮
  参考文献：
  名称：

  The Reactions of -Aminoalkyl Hydrogen Sulfates. I. The Preparation of Some Substituted Thiazolidine-2-thiones¹

  摘要：

  DOI：

  10.1021/jo01013a046

文献信息

• Aziridine formation by lithium aluminum hydride reduction of oximes
  作者：K. Kotera、S. Miyazaki、H. Takahashi、T. Okada、K. Kitahonoki

  DOI：10.1016/s0040-4020(01)92001-0

  日期：1968.1

  The azirine formation by LAH reduction of oximes has been extended to several types, such asandThe result was satisfactory to generalization of this reaction.

  通过LAH还原肟形成的叠氮基已扩展为多种类型，例如和，其结果对于该反应的一般化是令人满意的。
• Cycloaddition of Aziridine with CO₂/CS₂ Catalyzed by Amidato Divalent Lanthanide Complexes
  作者：Yueqin Xie、Chengrong Lu、Bei Zhao、Qianyu Wang、Yingming Yao

  DOI：10.1021/acs.joc.8b02924

  日期：2019.2.15

  Eu (1); n = 2, Ln = Eu (3), Yb (4); HL1 = tBuC6H4CONHC6H3(iPr)2; HL2 = C6H5CONHC6H3(iPr)2) and L3Eu[N(SiMe3)2]THF}L32Eu(THF)2} (2) (HL3 = ClC6H4CONHC6H3(iPr)2)) were applied in the cycloaddition reactions of aziridines with carbon dioxide (CO2) or carbon disulfide (CS2) under mild conditions. The corresponding oxazolidinones and thiazolidine-2-thiones were obtained in good to excellent yields with

  这是酰胺酰胺镧酰胺（L n Ln [N（SiMe 3）2 ] THF}} 2（n = 1，Ln = Eu（1）; n = 2，Ln = Eu（3），Yb （4）； HL 1＝t BuC 6 H 4 CONHC 6 H 3（i Pr）2； HL 2＝ C 6 H 5 CONHC 6 H 3（i Pr）2）和L 3Eu [N（SiMe 3）2 ] THF} L 3 2 Eu（THF）2 }（2）（HL 3 = ClC 6 H 4 CONHC 6 H 3（i Pr）2））被用于以下反应的环加成反应：氮丙啶与二氧化碳（CO 2）或二硫化碳（CS 2）在温和的条件下。获得了相应的恶唑烷酮和噻唑烷-2-硫酮，具有良好的收率和优异的官能团耐受性。
• Tandem electrocatalytic aziridination – ring expansion of simple aromatic olefins using ammonia and carbon dioxide
  作者：Jef R. Vanhoof、Robin Dirix、Dirk E. De Vos

  DOI：10.1039/d2gc03879j

  日期：——

  olefins with NH3 and CO2 or CS2 in a telescoped sequence is reported, forming 2-oxazolidinones or 2-thiazolidinethiones. The reaction proceeds via a N–H aziridine, which subsequently undergoes ring expansion with CO2 or CS2. Both steps are mediated by the same simple iodide catalyst and total yields of up to 91% referring to the alkene are achieved with excellent regioselectivities. This sustainable

  N-杂环是在有机合成和应用中经常出现的重要结构基序。因此，非常需要使用烯烃等常见起始原料的直接和绿色合成方法。在此，报道了芳香族烯烃与 NH 3和 CO 2或 CS 2以伸缩序列进行无金属电化学偶联，形成 2-恶唑烷酮或 ​​2-噻唑烷硫酮。该反应通过N-H 氮丙啶进行，随后与 CO 2或 CS 2发生扩环. 这两个步骤均由相同的简单碘化物催化剂介导，并且以出色的区域选择性实现了高达 91% 的烯烃总收率。这种使用现成材料的可持续反应具有出色的原子效率，只有 H 2作为潜在有用的副产物。
• ROTH; SCHLUMP, Archiv der Pharmazie, 1963, vol. 296, p. 213 - 217
  作者：ROTH、SCHLUMP

  DOI：——

  日期：——
• Hirashima, Akinori; Yoshii, Yutuka; Eto, Morifusa, Agricultural and Biological Chemistry, 1991, vol. 55, # 10, p. 2537 - 2546
  作者：Hirashima, Akinori、Yoshii, Yutuka、Eto, Morifusa

  DOI：——

  日期：——