S,S-dimethyl-N-(2-thiazolyl)sulfilimine | 130408-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: S,S-dimethyl-N-(2-thiazolyl)sulfilimine
• 英文别名: 1,1-dimethyl-N-(thiazol-2-yl)-λ⁴-sulfanimine；Dimethyl(1,3-thiazol-2-ylimino)-lambda4-sulfane；dimethyl(1,3-thiazol-2-ylimino)-λ4-sulfane
• CAS: 130408-28-5
• 化学式: C₅H₈N₂S₂
• 分子量: 160.264
• InChiKey: UPAZJYWZTRDBJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,4-二甲基-N-(苯基乙炔基)苯磺酰胺 、 S,S-dimethyl-N-(2-thiazolyl)sulfilimine 在 dichloro(2-picolinato)gold(III) 作用下， 以 甲苯 为溶剂， 以78%的产率得到N,4-dimethyl-N-(5-phenylimidazo[2,1-b]thiazol-6-yl)benzenesulfonamide
  参考文献：
  名称：

  N-吡啶基亚砜亚胺作为α-氨基金卡宾的来源：获得2-氨基取代的N-氨基咪唑

  摘要：

  据报道，在容易获得的N-吡啶基亚磺酰亚胺和酰胺类之间，金催化了正式的1,3-偶极环化。由相应的亚硫亚胺和乙酰胺制备各种咪唑衍生物。这些官能化的环状产物可以进行进一步的转化以提供各种咪唑骨架。此外，原位合成是可行的，并且在核苷类似物的合成中显示出良好的潜力。

  DOI：

  10.1021/acs.orglett.9b00140
• 作为产物：
  描述：

  2-氨基噻唑 、 二甲基硫 在 N-氯代丁二酰亚胺 、 sodium methylate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 2.17h， 以62%的产率得到S,S-dimethyl-N-(2-thiazolyl)sulfilimine
  参考文献：
  名称：

  N-吡啶基亚砜亚胺作为α-氨基金卡宾的来源：获得2-氨基取代的N-氨基咪唑

  摘要：

  据报道，在容易获得的N-吡啶基亚磺酰亚胺和酰胺类之间，金催化了正式的1,3-偶极环化。由相应的亚硫亚胺和乙酰胺制备各种咪唑衍生物。这些官能化的环状产物可以进行进一步的转化以提供各种咪唑骨架。此外，原位合成是可行的，并且在核苷类似物的合成中显示出良好的潜力。

  DOI：

  10.1021/acs.orglett.9b00140

文献信息

• A new approach to N-aryl- and N-(2-heteroaryl)imidates from chromium carbenes and sulfilimines
  作者：Benito Alcaide、Gema Dominguez、Joaquin Plumet、Miguel A. Sierra

  DOI：10.1021/om00047a007

  日期：1991.1

  Irradiation of pentacarbonyl(alkoxymethylcarbene)chromium(0) complexes in the presence of a number of N-aryl- or N-heteroaryl-substituted sulfilimines gives N-aryl- or N-heteroarylimidates in fair to excellent yields.
• Reaction of chromium (Fischer) carbenes and sulfilimines
  作者：Benito Alcaide、Luis Casarrubios、Gema Dominguez、Miguel A. Sierra

  DOI：10.1021/jo00067a020

  日期：1993.7

  The photochemical reactions of alkoxychromium (Fischer) carbenes and sulfilimines lead to imidates in fair to excellent yields. Aromatic, heteroaromatic, and alkylsulfilimines, the latter bearing functional groups such as cyano, sulfone, ether, ester, and dioxolane groups, gave the corresponding imidates in good to excellent yield. However, acyl- and sulfonyl-substituted sulfilimines did not react with chromium carbenes, except for sulfilimines bearing ethoxycarbonyl and phtalimidylamino groups. A variety of differently substituted chromium carbene complexes bearing alkyl, cycloalkyl, styryl, allyl, and alkynyl groups attached either at the carbene carbon or at the oxygen also gave imidates in good yields. For alpha,beta-unsaturated carbenes, the exclusive 1,2-addition of the sulfilimine nitrogen was observed at room temperature, in contrast to the behavior of other nitrogen nucleophiles which are reported to add in 1,4-fashion under these reaction conditions. In turn, optically active imidates of the type ArN=C(OR*)Me [R* = chiral substituent derived from (R)-(+)-1-phenyl-1-butanol, l-(-)-menthol, (1S)-endo-(-)-borneol, and (1R)-(-)-myrtenol] can be prepared efficiently by utilizing the corresponding chiral alkoxy group on the earbene moiety. The reactions above also occur in the dark but reaction times are considerably longer. N-Halosulfilimines reacted with alkoxychromium carbenes to yield N-acylsulfilimines instead of the expected N-haloimidates. Based upon a set of thermal and photochemical reactions between N-haloimidates and diphenyl sulfide in the absence of chromium complexes, the complex (CO)5CrNCMe is proposed to be responsible for this novel reaction of N-haloimidates and diphenyl sulfide.
• <i>N</i>-Pyridinyl Sulfilimines as a Source for α-Imino Gold Carbenes: Access to 2-Amino-Substituted <i>N</i>-Fused Imidazoles
  作者：Xianhai Tian、Lina Song、Matthias Rudolph、Qian Wang、Xinlong Song、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1021/acs.orglett.9b00140

  日期：2019.3.15

  ynamides is reported. A diverse set of imidazole derivatives is prepared from the corresponding sulfilimines and ynamides. These functionalized cyclic products can undergo further transformations to afford diverse imidazole frameworks. Moreover, in situ synthesis is feasible and shows good potential in the synthesis of nucleoside analogues.

  据报道，在容易获得的N-吡啶基亚磺酰亚胺和酰胺类之间，金催化了正式的1,3-偶极环化。由相应的亚硫亚胺和乙酰胺制备各种咪唑衍生物。这些官能化的环状产物可以进行进一步的转化以提供各种咪唑骨架。此外，原位合成是可行的，并且在核苷类似物的合成中显示出良好的潜力。