1,1-dimethyl-N-(pyrimidin-2-yl)-λ⁴-sulfanimine | 54214-58-3

• 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-(pyrimidin-2-yl)-λ⁴-sulfanimine
• 英文别名: S,S-dimethyl-N-(2-pyrimidinyl)sulfilimine；S,S-dimethyl-N-(2-pyrimidinyl)sulfimide；S,S-dimethyl-N-pyrimidin-2-ylsulfate；S,S-dimethyl-N-pyrimidin-2-yl-sulfimide；S,S-Dimethyl-N-pyrimidin-2-ylsulfimid；Dimethyl(pyrimidin-2-ylimino)-lambda4-sulfane；dimethyl(pyrimidin-2-ylimino)-λ4-sulfane
• CAS: 54214-58-3
• 化学式: C₆H₉N₃S
• 分子量: 155.224
• InChiKey: UWSULPLMMVSINF-UHFFFAOYSA-N

物化性质

• 沸点：
  321.7±25.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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-(pyrimidin-2-yl)-λ⁴-sulfanimine 在 二甲基硫 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 (9CI)-2-亚硝基-嘧啶
  参考文献：
  名称：

  Conversion of a primary amino group into a nitroso group. Synthesis of nitroso-substituted heterocycles

  摘要：

  DOI：

  10.1021/jo00342a035
• 作为产物：
  描述：

  1,3,5-三嗪-2,4,6-三胺,N,N'''-1,2-乙二基二[N-[3-[[4,6-二[丁基(2,2,6,6-四甲基-4-哌啶基)氨基]-1,3,5-三嗪-2-基]氨基]丙基]-N,N''-二丁基-N,N''-二(2,2,6,6-四甲基-4-哌啶基)- 、 二甲基硫 在 N-氯代丁二酰亚胺 、 sodium methylate 作用下， 生成 1,1-dimethyl-N-(pyrimidin-2-yl)-λ⁴-sulfanimine
  参考文献：
  名称：

  Preparation and biological evaluation of novel leucomycin analogs derived from nitroso Diels–Alder reactions

  摘要：

  利用白霉素 A7 的亚硝基 DielsâAlder 反应合成了一系列 10,13-二取代 16 元大环内酯类化合物。尽管白霉素中含有大量的组成官能团，但杂环加成反应仍以高度区域和立体选择性的方式进行。随后还对亚硝基环加成物进行了化学修饰，包括 NâO 键还原。大多数白霉素衍生物保留了与白霉素 A7 相似的抗生素特性，与白霉素本身不同的是，其中几种衍生物表现出适度的抗增殖和细胞毒性活性。

  DOI：

  10.1039/b922450e

文献信息

• Polyhedral rearrangements in undeca- and dodeca-nuclear Group 1B metal osmium clusters
  作者：Simon R. Drake、Brian F. G. Johnson、Jack Lewis

  DOI：10.1039/dt9890000505

  日期：——

  been explored, and found to yield the mixed metal clusters [Os10C(CO)24M(PR3)}Cu(NCMe)}][M = Au, PR3= PPh3(5a), or PEt3(5b); M = Ag, PR3= PPh3(5c)] and [Os10(H)C(CO)24M(PPh3)}][M = Au (6a), Ag (6b), or Cu (6c)]. The reaction of (6a) or (6b) with AgClO4yields the known eicosaosmium cluster [Os20M(C)2(CO)48]2–[M = Au (7a) or Ag (7b)]. These dianionic clusters have been found to be readily reduced by

  一系列异核簇[Os 10 C（CO）24 M（PR 3）} 2 ] [M = Au，PR 3 = PMe 2 Ph（2a）; M = Ag，PR 3 = PPh 3（2d）]，[Os 10 C（CO）24 Au（PEt 3）} Ag（PPh 3）}]（2e），[Os 10 C（CO）24 Au（PMe 2 Ph）} 3 ] [ClO 4 ]（3）和[Os 10 C（CO）24 M（PR 3）}]– [M = Au，PR 3 = PMe 2 Ph（ 4a）；M ＝ Ag，PR 3＝ PPh 3（ 4d）；M ＝ Ag，PR 3＝ PPh 3（ 4d）。M = Cu，PR 3 = PPh 3（ 4e）]已经制备并显示出在溶液中发生分子重排；（ 2a），（ 2e）和（ 4a）的两种异构形式已被鉴定，它们的相互转化被认为涉及cap⇆边缘桥⇆cap（cec）途径。[Os 10 C（CO）
• <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。
• 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
• 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.