3-Phenyl-4-oxo-thiazolidin | 22396-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Phenyl-4-oxo-thiazolidin
• 英文别名: 3-Phenyl-4-thiazolidinone；3-phenyl-1,3-thiazolidin-4-one
• CAS: 22396-54-9
• 化学式: C₉H₉NOS
• 分子量: 179.243
• InChiKey: RRNZCBCXCGGYFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Phenyl-4-oxo-thiazolidin 、 丙烯酸甲酯（MA） 在 silver hexafluoroantimonate 、 (p-cymene)ruthenium(II) chloride 、 氧气 、 copper(II) acetate monohydrate 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 18.0h， 以24%的产率得到
  参考文献：
  名称：

  Ruthenium(II)-Catalyzed C–H Functionalization Using the Oxazolidinone Heterocycle as a Weakly Coordinating Directing Group: Experimental and Computational Insights

  摘要：

  Herein, we report the ruthenium-catalyzed ortho C-H alkenylation of a wide range of N-aryloxazolidinone scaffolds. Alkenylation was achieved with complete mono selectivity with a scope of 27 examples in 2-MeTHF. Yields ranged from 23 to 94%, producing highly decorated oxazolidinone scaffolds. A kinetically relevant C-H cleavage was also observed with a kinetic isotope effect (KIE) of similar to 2. Density functional theory calculations provided information about mechanism, detailing the beta-hydride elimination as the most energetically challenging step of 13.5 kcal mol(-1). In-depth computational kinetic studies also predicted a KIE of 2.17 for C-H cleavage and an intrinsic KIE for the reaction of 2.22, in line with the experimentally observed value.

  DOI：

  10.1021/acscatal.6b01370
• 作为产物：
  描述：

  N-Phenyl-rhodanin 在 盐酸 、 乙醇 、 锌 作用下， 生成 3-Phenyl-4-oxo-thiazolidin
  参考文献：
  名称：

  Andreasch, Monatshefte fur Chemie, 1928, vol. 49, p. 125

  摘要：

  DOI：

文献信息

• 2-(Benzoylimino)thiazolidin-4-ones: Formation by an Alternative Ring Closure and Analysis of Rotational Barriers
  作者：Michael Gütschow、Hans-Georg Häcker、Paul Elsinghorst、Susanne Michels、Jörg Daniels、Gregor Schnakenburg

  DOI：10.1055/s-0028-1087995

  日期：2009.4

  The reactions of N-benzoyl-N′-(o-cyanoaryl)thioureas with ethyl bromoacetate under alkaline conditions led to the form­ation of either fused 2-(alkylsulfanyl)-4-aminopyrimidines or 2-(benzoylimino)-3-(o-cyanoaryl)thiazolidin-4-ones. The accurate application of slightly different reaction conditions allowed us to adjust the balance between the formation of the pyrimidine or thiazolidine heterocycles. Atropisomerism in the 3-(o-cyanoaryl)thiazolidin-4-ones was influenced by the size of the o-cyanoaryl ring, which was investigated by means of NMR measurements and theoretical calculations.

  在碱性条件下，N-苯甲酰基-N′-（邻氰基芳基）硫脲与溴乙酸乙酯反应，生成融合的 2-（烷基硫酰基）-4-氨基嘧啶或 2-（苯甲酰基亚氨基）-3-（邻氰基芳基）噻唑烷-4-酮。通过准确地应用略有不同的反应条件，我们可以调整嘧啶或噻唑烷杂环形成之间的平衡。3-(o-氰基芳基)噻唑烷-4-酮中的异构体受邻氰基芳基环大小的影响，这一点通过核磁共振测量和理论计算进行了研究。
• Zur Synthese von 4-Thiazolidonderivaten
  作者：W. Pacha、H. Erlenmeyer

  DOI：10.1002/hlca.19560390417

  日期：——

  Derivatives of 4-thiazolidone are obtained by reaction of mercaptoacetanilicle with 1, 1-dihalogen compounds.

  4-噻唑烷酮的衍生物是通过巯基乙腈与1，1-二卤素化合物的反应获得的。
• Herbicidally active phenylsubstituted 5-and 6-membered heterocyclic
  申请人：Zeneca Limited

  公开号：US05856273A1

  公开（公告）日：1999-01-05

  A compound of formula (I): ##STR1## where E is oxygen or sulphur; A is CR.sup.3 or N where R.sup.3 is hydrogen or hydrocarbyl; D completes a 5 or 6-membered non-aromatic heterocyclic ring which optionally contains additional heteroatoms selected from oxygen, nitrogen or sulphur and which is optionally substituted by an optionally substituted lower hydrocarbyl group, or an optionally substituted heteroaryl group; R.sup.1 and R.sup.2 are each independently hydrogen; optionally substituted lower hydrocarbyl, or optionally substituted heteroaryl, or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached, form a heterocyclic ring; Z represents halogen optionally substituted lower hydrocarbyl, optionally substituted lower hydocarbyloxy, optionally substituted lower hydrocarbylthio, hydrocarbylsulphinyl or hydrocarbylsulphonyl, cyano, nitro, CHO, NHOH, ONR.sup.7' R.sup.7", SF.sub.5 ; CO (optionally substituted lower hydrocarbyl), acylamino, COOR.sup.7, SO.sub.2 NR.sup.8 R.sup.9, CONR.sup.10 R.sup.11, OR.sup.12 or NR.sup.13 R.sup.14 where R.sup.7, R.sup.7', R.sup.7", R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are independently hydrogen or lower hydrocarbyl; R.sup.12 is hydrogen; SO.sub.2 lower hydrocarbyl or COR.sup.15 ; R.sup.13 and R.sup.14 are independently lower hydrocarbyl, lower hydrocarbyloxy or a group R.sup.12 ; R.sup.15 is OR.sup.16, NR.sup.17 R.sup.18, hydrogen or lower hydrocarbyl; R.sup.16 is lower hydrocarbyl; R.sup.17 and R.sup.18 are independently hydrogen or lower hydrocarbyl; provided that when there are two or more substituents Z, they may be the same or different; and m is 0 or an integer from 1 to 5.

  化合物的化学式（I）：##STR1## 其中E是氧或硫；A是CR.sup.3或N，其中R.sup.3是氢或烃基；D完成一个5或6元非芳杂环，该环可以选择性地包含来自氧、氮或硫的额外杂原子，并且可以被一个选择性地取代的较低烃基团或一个选择性地取代的杂环基团取代；R.sup.1和R.sup.2各自独立地是氢、选择性取代的较低烃基、选择性取代的杂环基，或者R.sup.1和R.sup.2与它们附着的氮原子一起形成一个杂环；Z代表卤素选择性取代的较低烃基、选择性取代的较低羟基烃基氧、选择性取代的较低硫基烃基、烃基磺酰基或烃基磺酸基、氰基、硝基、CHO、NHOH、ONR.sup.7' R.sup.7"、SF.sub.5；CO（选择性取代的较低烃基）、酰基氨基、COOR.sup.7、SO.sub.2 NR.sup.8 R.sup.9、CONR.sup.10 R.sup.11、OR.sup.12或NR.sup.13 R.sup.14，其中R.sup.7、R.sup.7'、R.sup.7"、R.sup.8、R.sup.9、R.sup.10和R.sup.11独立地是氢或较低烃基；R.sup.12是氢；SO.sub.2较低烃基或COR.sup.15；R.sup.13和R.sup.14独立地是较低烃基、较低烃基氧或一个R.sup.12基团；R.sup.15是OR.sup.16、NR.sup.17 R.sup.18、氢或较低烃基；R.sup.16是较低烃基；R.sup.17和R.sup.18独立地是氢或较低烃基；但是，当有两个或更多的取代基Z时，它们可以相同或不同；m为0或1到5的整数。
• Silver halide light sensitive emulsion layer having enhanced photographic sensitivity
  申请人：EASTMAN KODAK COMPANY

  公开号：EP0786692A1

  公开（公告）日：1997-07-30

  A photographic element comprises at least one silver halide emulsion layer in which the silver halide is sensitized with a compound of formula         Z-(L-XY)k wherein: Z is a light absorbing group; L is a linking group containing a least one C, N, S, or O atom; and k is 1 or 2; and XY represents a fragmentable electron donor moiety wherein: 1) XY has a an oxidation potential between 0 and about 1.4 V; 2) X is an electron donor group; 3) Y is a leaving group other than hydrogen; and 4) the oxidized form of XY undergoes a bond cleavage reaction to give the radical X• and the leaving fragment Y. In a preferred embodiment the radical X• has an oxidation potential of ≤ -0.7 V.

  感光元件包括至少一个卤化银乳剂层，其中的卤化银是用式 1 的化合物感光的。 Z-(L-XY)k 其中 Z 是光吸收基团 L 是连接基团，含有至少一个 C、N、S 或 O 原子的连接基团；以及 k 是 1 或 2；以及 XY 代表可碎裂的电子供体分子，其中 1) XY 的氧化电位在 0 至约 1.4 V 之间； 2) X 是电子供体基团 3) Y 是氢以外的离去基团；以及 4) XY 的氧化形式发生键裂反应，生成自由基 X- 和离去片段 Y。 在一个优选的实施方案中，自由基 X- 的氧化电位≤ -0.7 V。
• Photobleachable composition, photographic element containing the composition and photobleach method
  申请人：EASTMAN KODAK COMPANY

  公开号：EP1134613A1

  公开（公告）日：2001-09-19

  A UV or visible-light sensitive photobleachable dye composition substantially free of polymerisable monomer comprising a photobleachable dye and an N-oxyazinium compound, a photographic element containing such a photobleachable composition, and a method for bleaching a photographic element.

  一种基本上不含可聚合单体的紫外线或可见光敏感光漂白染料组合物，该组合物包含一种光漂白染料和一种 N-氧嗪化合物；一种含有这种光漂白组合物的感光元件；以及一种对感光元件进行漂白的方法。