5-benzylidene-3-phenyl-2-thioxothiazolidin-4-one | 13037-56-4

• 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: 5-benzylidene-3-phenyl-2-thioxothiazolidin-4-one
• 英文别名: 3-phenyl-5-phenylmethylidene-4-oxo-2-thioxo-1,3-thiazolidine；5-phenylmethylene-3-phenyl-2-thioxo-1,3-thiazolidin-4-one；3-phenyl-5-benzylidene-2-thioxo-4-thiazolidinone；5-Benzyliden-3-phenyl-2-thioxothiazolidin-4-on；5-benzylidene-3-phenyl-2-thioxo-thiazolidin-4-one；5-Benzyliden-3-phenyl-2-thioxo-thiazolidin-4-on；4-Thiazolidinone, 3-phenyl-5-(phenylmethylene)-2-thioxo-, (5Z)-；5-benzylidene-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 13037-56-4
• 化学式: C₁₆H₁₁NOS₂
• mdl: MFCD00642795
• 分子量: 297.401
• InChiKey: TZPSGDWUSVAMNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  5-benzylidene-3-phenyl-2-thioxothiazolidin-4-one 在 sodium t-butanolate 作用下， 以 叔丁醇 为溶剂， 反应 7.0h， 生成 4,7-Diphenyl-2,6-dithia-4-aza-bicyclo[3.2.0]hept-1(5)-ene-3-thione
  参考文献：
  名称：

  Yadav; Dubey, Suman; Singh, Smita, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 6, p. 1234 - 1237

  摘要：

  DOI：
• 作为产物：
  描述：

  3-苯基-2-硫酮-1,3-噻唑啉-4-酮 、 5-benzylidene-2-morpholino-1,3-thiazol-4(5H)-one 在 sodium 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以72%的产率得到5-benzylidene-3-phenyl-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  Reactions of N,N-Disubstituted 5-Arylmethylidene-2-amino-thiazol-4(5H)-ones with CH Acids

  摘要：

  N,N-Disubstituted 5-arylmethylidene-2-aminothiazol-4(5H)-ones reacted with diethyl malonate, ethyl benzoylacetate, acetylacetone, or cyclopentadiene in refluxing toluene and in presence of powdered sodium to give the respective 5-arylmethylidene-2'-amino-2,5'-bithiazolylidene-4,4'-dione derivatives in moderate yields. 5-Benzylidene-2-morpholin-4-yl-2-thiazol-4(5H)-one reacted with malononitrile in toluene and in presence of powdered sodium under mild conditions to afford the 1:1 adduct, benzylmalononitrile, and 2-morpholin-4-yl-2-thiazol-4(5H)-one. However, similar treatment of 5-(4-methoxyphenylmethylidene)-2-morpholin-4-yl-2-thiazol-4(5H)-one with malononitrile yielded the 2,5'-bithiazolylidene-4,4'-dione derivative together with 4-methoxyphenylmethylidene malononitrile. Treatment of 5-benzylidene- and 5-(4-methoxyphenylmethylidene)-2-morpholin-4-yl-2-thiazol-4(5H)-ones with 3-phenyl-4-oxo-2-thioxo-1,3-thiazolidine in refluxing toluene and in presence of powdered sodium produced 5-arylmethylidene-3-phenyl-4-oxo-2-thioxo-1,3-thiazolidines in good yields. The structures of all products were deduced from microanalytical and spectroscopic data, mechanistic details are discussed.

  DOI：

  10.1007/s007060200092

文献信息

• A New Strategy for Synthesis of Novel 1, 4-Phenylene Bridged Bis-Hetero - Cyclic Compounds
  作者：Hamdi M. Hassaneen、Ahmad S. Shawali、Lamiaa M. El Agaty

  DOI：10.2174/1570178613666160824104435

  日期：2016.10.25

  Reactions of bis-hydrazonoyl chloride 1 with each of KSCN and KSeCN yielded the corresponding bis-thiadiazoline 2A and bis-selenadiazoline 2B. Bispyrazole derivatives 7a-e and 8a-b were also obtained by reactions of 1 with the appropriate active methylene compounds. Reactions of 1 with each of 1, 2- dicyanoethylene, acenaphthylene and phenyl-5-arylidene-2-thioxo-thiazol-4-one as dipolarophiles led to the formation of the corresponding cycloadducts 9, 12 and 14, respectively. Also, reaction of bis-hydrazonoyl chloride 1 with triazinethione 16a-e afforded 1,4-Bis-(1,2,4-triazolotriazin)benzene 17a-e. The structures of the compounds prepared were established on the basis of elemental and spectral analyses as well as their chemical reactions.

  二氢腙基氯1与KSCN和KSeCN分别反应，生成了相应的双硫二氮杂环2A和双硒二氮杂环2B。通过1与适当的活性亚甲基化合物的反应，还得到了双吡唑衍生物7a-e和8a-b。1与二氰基乙烯、苊烯和苯基-5-芳亚甲基-2-硫酮-噻唑-4-酮作为双极亲偶体的反应分别导致了相应的环加成产物9、12和14的形成。此外，二氢腙基氯1与三嗪硫酮16a-e反应生成了1,4-双-(1,2,4-三唑三嗪)苯17a-e。所制备化合物的结构是根据元素和光谱分析以及它们的化学反应来确定的。
• Asymmetric construction of spirocyclohexanonerhodanines catalyzed by simple diamine derived from chiral tert-leucine
  作者：Wenbin Wu、Huicai Huang、Xiaoqian Yuan、Kailong Zhu、Jinxing Ye

  DOI：10.1039/c2cc34321e

  日期：——

  A diamine-catalyzed asymmetric tandem reaction between alpha,beta-unsaturated ketones and rhodanine derivatives has been developed to synthesize various spirocyclic compounds with high stereoselectivities (up to 99% ee and >20:1 dr). The products obtained contain two pharmaceutically relevant features: the biologically active rhodanine moiety embedded in a spirocyclic unit.

  α，β-不饱和酮和绕丹宁衍生物之间的二胺 - 催化的不对称串联反应已经发展到合成具有高立体选择性的各种螺化合物（高达99％ee值和> 20：1个，DR）。得到的产物含有两种药物的相关特征：嵌入在螺环单元中的生物活性绕丹宁部分。
• Alkynylation of heterocyclic compounds using hypervalent iodine reagent
  作者：M. Kamlar、I. Císařová、J. Veselý

  DOI：10.1039/c4ob02625j

  日期：——

  The alkynylation of various nitrogen- and/or sulphur-containing heterocyclic compounds using hypervalent iodine TMS-EBX by utilization of tertiary amines under mild conditions is described.

  描述了利用三级胺在温和条件下利用高价碘TMS-EBX对各种含氮和/或硫杂环化合物进行炔基化的过程。
• A convenient synthesis of novel 1,3-phenylene bridged<i>bis</i>-heterocyclic compounds
  作者：Hamdi M. Hassaneen、Ahmad S. Shawali、Fatma M. Saleh

  DOI：10.1080/17415993.2015.1126592

  日期：2016.5.3

  ABSTRACT Reactions of bis-hydrazonoyl bromide 1 with each of phenyl-5-arylidene-2-thioxo-thiazol-4-one, triazinethiones and 4,6-dimethyl-2,6-dioxocyclohexane-1-thiocarboxanilide as sulfur dipolarophilic reagents led to the formation of the hitherto unreported 1,3-phenylene bis-heterocycles 4, 8 and 10, respectively. The structures of the isolated products were established on the basis of their elemental

  摘要 双腙酰溴 1 与作为硫双极性试剂的苯基-5-亚芳基-2-硫代-噻唑-4-酮、三嗪硫酮和 4,6-二甲基-2,6-二氧代环己烷-1-硫代甲酰苯胺中的每一种的反应导致迄今为止未报道的 1,3-亚苯基双杂环 4、8 和 10 的形成。分离产物的结构是在元素和光谱分析的基础上建立的。讨论了所研究反应的机理和位点选择性。图形概要
• Aminocatalyzed asymmetric Diels–Alder reaction of 2,4-dienals and rhodanine/hydantoin derivatives
  作者：Kailong Zhu、Huicai Huang、Wenbin Wu、Yuan Wei、Jinxing Ye

  DOI：10.1039/c3cc00023k

  日期：——

  Aminocatalyzed asymmetric Diels-Alder reaction between 2,4-dienals and rhodanine/hydantoin derivatives via trienamine mechanism has been developed to synthesize various spirocyclic compounds with good yields (up to 98%) and excellent stereoselectivities (up to 99% ee and >19 : 1 dr).

  已经开发了通过三烯胺机理的2,4-二烯醛与若丹宁/乙内酰脲衍生物之间的氨基催化不对称Diels-Alder反应，以合成各种螺环化合物，具有良好的收率（高达98％）和出色的立体选择性（高达99％ee且> 19： 1博士）。