rac-3,4-diphenyl-4,5-dihydro-1,2,5-thiadiazoline-1,1-dioxide | 3775-16-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: rac-3,4-diphenyl-4,5-dihydro-1,2,5-thiadiazoline-1,1-dioxide
• 英文别名: 3,4-diphenyl-1,2,5-thiadiazoline 1,1-dioxide；3,4-diphenyl-2,3-dihydro-[1,2,5]thiadiazole 1,1-dioxide；3,4-Diphenyl-Δ²-1,2,5-thiadiazolin-1,1-dioxid；3,4-Diphenyl-1,2,5-Δ²-thiadiazolin-1,1-dioxid；1,2,5-Thiadiazole, 2,3-dihydro-3,4-diphenyl-, 1,1-dioxide；3,4-diphenyl-2,3-dihydro-1,2,5-thiadiazole 1,1-dioxide
• CAS: 3775-16-4
• 化学式: C₁₄H₁₂N₂O₂S
• 分子量: 272.327
• InChiKey: NXFKZSKXFALQSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rac-3,4-diphenyl-4,5-dihydro-1,2,5-thiadiazoline-1,1-dioxide 在 platinum(IV) oxide 氢气 、 potassium carbonate 作用下， 以 乙醇 、 苯 为溶剂， 生成 1,1-dioxo-3,4-diphenyl-1λ6-[1,2,5]thiadiazolidine-2,5-dicarboxylic acid bis-dimethylamide
  参考文献：
  名称：

  The Reaction of Sulfamide with α- and β-Diketones. The Preparation of 1,2,5-Thiadiazole 1,1-Dioxides and 1,2,6-Thiadiazine 1,1-Dioxides

  摘要：

  DOI：

  10.1021/jo01030a059
• 作为产物：
  描述：

  3,4-diphenyl-1,2,5-thiadiazole-1,1-dioxide 在 [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I) 、 甲酸 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以71%的产率得到rac-3,4-diphenyl-4,5-dihydro-1,2,5-thiadiazoline-1,1-dioxide
  参考文献：
  名称：

  Enantioselective Synthesis of 3,4-Disubstituted cis- and trans-1,2,5-Thiadiazolidine-1,1-dioxides as Precursors for Chiral 1,2-Diamines

  摘要：

  Both, cis- and trans-3,4-disubstituted thiadiazolidines 5 and 6 can enantioselectively be obtained from thiadiazoles 2 which, in turn, are efficiently prepared from the respective 1,2-diketone by an improved protocol. An asymmetric ruthenium-catalyzed transfer hydrogenation followed by a diastereoselective hydride addition furnishes exclusively the cis-isomers 5 which, under acidic conditions, undergo a novel isomerization into the trans-isomers 6. These cyclic sulfamides can be transformed into 1,2-diamines as well as 2,3-diamino acids.

  DOI：

  10.1021/ol3034753

文献信息

• The addition reaction of diamides to 1,2,5-thiadiazole 1,1-dioxide derivatives
  作者：José A. Caram、María V. Mirífico、Silvia L. Aimone、Oscar E. Piro、Eduardo E. Castellano、Enrique J. Vasini

  DOI：10.1002/poc.829

  日期：2004.12

  4-bis(p-methoxyphenyl)-(1b), phenanthro[9,10-c]-(1c) and acenaphtho[1,2-c]-1,2,5-thiadiazole 1,1-dioxide (1d), 3,4-diphenyl-1,2,5-thiadiazoline 1,1-dioxide (2a) and 4-ethoxy-5-methyl-3,4-diphenyl-1,2,5-thiadiazoline 1,1-dioxide (2b)], with reagents possessing two nucleophilic nitrogen atoms (urea, N,N′-dimethylurea, thiourea, N-methylthiourea, N-ethylthiourea, N-allylthiourea, N,N′-diethylthiourea, N,N′-diphenylthiourea

  1,2,5-噻二唑1,1-二氧化物[3,4-二苯基-（1a），3,4-双（对甲氧基苯基）-（1b），菲[9,10- c ]-（1c）和ena [1,2-c] -1,2,5-噻二唑1,1-二氧化物（1d），3,4-二苯基-1,2,5-噻二唑啉1,1-二氧化物（图2a）和4-乙氧基-5-甲基-3,4-二苯基-1,2,5-噻二唑啉-1,1-二氧化物（2B）]，其中具有两个亲核氮原子的试剂（尿素，ñ，ñ ' -二甲基脲，硫脲，ñ -methylthiourea，ñ -ethylthiourea，ñ -allylthiourea，ñ，Ñ '-diethylthiourea，Ñ，Ñ '-diphenylthiourea，dithioxamide和磺酰胺），其次是循环伏安法（CV），并在非质子传递溶剂中的溶液的UV可见分光光度法。分离产物，通过IR，1 H NMR和13 C NMR方法表征，并通过单晶X
• Reactions of 1,2,5-thiadiazole 1,1-dioxide derivatives with nitrogen nucleophiles. Part IV. Addition of<i>α</i>-diamines
  作者：María Virginia Mirífico、José Alberto Caram、Enrique Julio Vasini、Oscar Enrique Piro、Eduardo E. Castellano

  DOI：10.1002/poc.1444

  日期：2009.2

  The new compound acenaphtho [5,6‐b]‐2,3‐dihydropyrazine was synthesized and characterized. The addition of ethylendiamine to 3,4‐diphenyl‐ 1,2,5‐thiadiazoline 1,1‐dioxide gives 3,4‐disubstituted thiadiazolidine 1,1‐dioxide, dihydropyrazines, or pyrazines, depending on the reaction condition used. The reactions were followed by cyclic voltammetry and NMR spectroscopy which, in some cases, allowed the detection

  α-二胺，例如乙二胺和邻苯二胺，分别加到3,4-芳基-二取代的1,2,5-噻二唑1,1-二氧化物中，分别得到二氢吡嗪或喹喔啉和亚磺酰胺。合成并表征了新化合物[5,6-b] -2-，3-二氢吡嗪。根据所使用的反应条件，将乙二胺加到3,4-二苯基-1,2,5-噻二唑啉1,1-二氧化物中可得到3,4-二取代的噻二唑烷1,1-二氧化物，二氢吡嗪或吡嗪。反应之后是循环伏安法和NMR光谱法，在某些情况下，可以检测噻二唑烷中间体。版权所有©2008 John Wiley＆Sons，Ltd.
• The Reaction of Sulfamide with α- and β-Diketones. The Preparation of 1,2,5-Thiadiazole 1,1-Dioxides and 1,2,6-Thiadiazine 1,1-Dioxides
  作者：John B. Wright

  DOI：10.1021/jo01030a059

  日期：1964.7
• Enantioselective Synthesis of 3,4-Disubstituted <i>cis</i>- and <i>trans</i>-1,2,5-Thiadiazolidine-1,1-dioxides as Precursors for Chiral 1,2-Diamines
  作者：Christian Schüttler、Zhen Li-Böhmer、Klaus Harms、Paultheo von Zezschwitz

  DOI：10.1021/ol3034753

  日期：2013.2.15

  Both, cis- and trans-3,4-disubstituted thiadiazolidines 5 and 6 can enantioselectively be obtained from thiadiazoles 2 which, in turn, are efficiently prepared from the respective 1,2-diketone by an improved protocol. An asymmetric ruthenium-catalyzed transfer hydrogenation followed by a diastereoselective hydride addition furnishes exclusively the cis-isomers 5 which, under acidic conditions, undergo a novel isomerization into the trans-isomers 6. These cyclic sulfamides can be transformed into 1,2-diamines as well as 2,3-diamino acids.