1,1-dimethyl-N-(pyrazin-2-yl)-λ⁴-sulfanimine | 62135-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,1-dimethyl-N-(pyrazin-2-yl)-λ⁴-sulfanimine
• 英文别名: S,S-dimethyl-N-(2-pyrazinyl)sulfilimine；S,S-dimethyl-N-(2-pyrazinyl)sulfimide；S,S-dimethyl-N-(2-pyrazyl)sulfilimine；S,S-dimethyl-N-pyrazin-2-yl-sulfimide；S,S-dimethyl-N-pyrazinyl-sulfimide；SS-Dimethyl-N-pyrazinylsulfimid；Dimethyl(pyrazin-2-ylimino)-lambda4-sulfane；dimethyl(pyrazin-2-ylimino)-λ4-sulfane
• CAS: 62135-46-0
• 化学式: C₆H₉N₃S
• 分子量: 155.224
• InChiKey: HOZDUQOYAWEABS-UHFFFAOYSA-N

物化性质

• 沸点：
  306.1±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-dimethyl-N-(pyrazin-2-yl)-λ⁴-sulfanimine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-nitrosopyrazine
  参考文献：
  名称：

  Syntheses and Biological Activity Studies of Novel Sterol Analogs from Nitroso Diels−Alder Reactions of Ergosterol

  摘要：

  A series of novel sterol analogs was prepared using nitroso Diels-Alder reactions with ergosterol. Most cycloaddition reactions proceeded in an excellent regio- and stereoselective fashion. Further N-O bond cleavage of cycloadducts generated compounds with biological activity in PC-3 and MCF-7 cancer cell lines.

  DOI：

  10.1021/ol900997t
• 作为产物：
  描述：

  氨基吡嗪 、 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82%的产率得到1,1-dimethyl-N-(pyrazin-2-yl)-λ⁴-sulfanimine
  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

• Syntheses of New Spirocarbocyclic Nucleoside Analogs Using Iminonitroso Diels−Alder Reactions
  作者：Weimin Lin、Anuradha Gupta、Kyung Hee Kim、David Mendel、Marvin J. Miller

  DOI：10.1021/ol802553g

  日期：2009.1.15

  dienes coupled efficiently in a series of iminonitroso Diels−Alder reactions to produce a series of new spirocyclic adducts. Hydrogenolysis of these adducts afforded new spirocycles that contain multiple handles for further functionalization. Furthermore, stereocontrolled dihydroxylation and reductive cleavage of the spirocyclic adducts generated versatile scaffolds for the syntheses and derivatization

  N -Cbz-和Boc-保护的螺环二烯通过环戊二烯的二烷基化制备。这些二烯在一系列亚氨基亚硝基 Diels-Alder 反应中有效偶联，以产生一系列新的螺环加合物。这些加合物的氢解提供了新的螺环，其中包含用于进一步功能化的多个手柄。此外，螺环加合物的立体控制二羟基化和还原裂解为新型螺环碳环核苷类似物的合成和衍生化提供了多功能支架。
• [EN] BICYCLIC HETEROARYL DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DÉRIVÉS HÉTÉROARYLES BICYCLIQUES EN TANT QU'INHIBITEURS DE KINASE
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2013078254A1

  公开（公告）日：2013-05-30

  The present invention provides compounds, including resolved enantiomers, resolved diastereomers, solvates and pharmaceutically acceptable salts thereof, comprising the Formula 1: wherein Het, X, R1 and R2 are as defined herein.

  本发明提供了化合物，包括已分离的对映体、已分离的异构体、溶剂合物和其药学上可接受的盐，其化学式如下：其中Het、X、R1和R2的定义如本文所述。
• Synthesis of sulphimide complexes of palladium and platinum. Crystal and molecular structure of cis-dichloro[S,S-dimethyl-N-(2-pyrimidinyl)sulphimide](triphenyiphosphine)pailadium(II)
  作者：Jack L. Davidson、Peter N. Preston、Sally A. R. Spankie、Graeme Douglas、Kenneth W. Muir

  DOI：10.1039/dt9890000497

  日期：——

  = PPh3(4f)]. An X-ray analysis of cis-[PdCl2(PPh3)(Me2SNC4H3N2)]·CH2Cl2(4f) revealed that the pyrimidine rather than the sulphimide N atom is the point of attachment of the sulphimide ligand to Pd. Conformational energy calculations suggest that electronic rather than steric factors determine which N atom acts as donor to Pd. The crystals are monoclinic, space group P21/n, with a= 17.307(6), b= 9.182(1)

  [MCl 2（PhCN）2 ]（M = Pd或Pt）和K 2 [PtCl 4 ]与S，S-二甲基-N-杂芳族硫化亚胺Me 2 SNR（R = 2-吡啶基，4-甲基-2 -吡啶基，2-嘧啶基，4-甲基-2-嘧啶基或2-吡嗪基）得到反式-[M 2 Cl 2（μ-Cl）2（Me 2 SNR）2 ]（1）的1：1加合物根据1 H nmr研究，硫化亚胺似乎通过叶立德氮配位。[MCl 2（PhCN）2的反应]与Me 2 SNPh合成时，当M = Pd时生成双（硫化物）反式-[MCl 2（Me 2 NSPh）2 ]（2），而当M = Pt时，苯腈衍生物顺式-[PtCl 2（Me 2 SNPh）（获得NPh]]（3）。配合物（1）与膦L = PEt 3，PMe 2 Ph，PMePh 2或PPh 3反应，得到1：1的加合物[MCl 2 L（Me 2 SNR）] [M = Pd; R = 2-吡啶基，L = PEt
• 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.
• Conversion of a primary amino group into a nitroso group. Synthesis of nitroso-substituted heterocycles
  作者：Edward C. Taylor、Chi Ping Tseng、Jang B. Rampal

  DOI：10.1021/jo00342a035

  日期：1982.1