N-Phenyl-S,S-dimethyl-sulfimid | 20094-91-1

• 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: N-Phenyl-S,S-dimethyl-sulfimid
• 英文别名: N-Phenyl-S,S-dimethylsulfimid；dimethyl(phenylimino)-λ4-sulfane
• CAS: 20094-91-1
• 化学式: C₈H₁₁NS
• 分子量: 153.248
• InChiKey: NMUIMCVOBRAUIC-UHFFFAOYSA-N

物化性质

• 沸点：
  266.6±23.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Phenyl-S,S-dimethyl-sulfimid 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 以10.4 g的产率得到2-methylthiomethylaniline
  参考文献：
  名称：

  苯并[c]异噻唑2-氧化物：具有交叉耦合和功能化潜力的三维杂环

  摘要：

  已开发出一种可靠的合成苯并[ c ]异噻唑2-氧化物的方法，可提供从苯胺和DMSO开始的一系列功能化衍生物。反应顺序可以以克为单位进行，可以生成可以通过标准交叉偶联反应轻松修饰的产物。

  DOI：

  10.1002/adsc.201600823
• 作为产物：
  描述：

  二甲基亚砜 、 苯胺 在 三氟乙酸酐 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 N-Phenyl-S,S-dimethyl-sulfimid
  参考文献：
  名称：

  苯并[c]异噻唑2-氧化物：具有交叉耦合和功能化潜力的三维杂环

  摘要：

  已开发出一种可靠的合成苯并[ c ]异噻唑2-氧化物的方法，可提供从苯胺和DMSO开始的一系列功能化衍生物。反应顺序可以以克为单位进行，可以生成可以通过标准交叉偶联反应轻松修饰的产物。

  DOI：

  10.1002/adsc.201600823

文献信息

• The Reaction of 4,5-Dichloro-1,2,3-dithiazolium Chloride with Sulfimides: A New Synthesis of N-Aryl-1,2,3-dithiazolimines
  作者：Andreas Kalogirou、Panayiotis Koutentis

  DOI：10.3390/molecules14072356

  日期：——

  N-Aryl-S,S-dimethylsulfimides 3 (Ar = 4-NO2C6H4), 4 (Ar = Ph) and 5 (Ar = 4-Tol) react with Appel salt 1 to give the corresponding N-aryl-(4-chloro-5H-1,2,3-dithiazolylidene)benzenamines 8 (Ar = 4-NO2C6H4), 9 (Ar = Ph) and 10 (Ar = 4-Tol) in 84, 94 and 87% yields, respectively. The reaction proceeds in the absence of base and a proposed reaction mechanism is given.

  N-Aryl-S,S-二甲基亚砜 3 (Ar = 4-NO2C6H4)、4 (Ar = Ph) 和 5 (Ar = 4-Tol) 与 Appel 盐 1 反应得到相应的 N-芳基-(4-氯-5H-1,2,3-二噻唑亚基)苯胺 8 (Ar = 4-NO2C6H4)、9 (Ar = Ph) 和 10 (Ar = 4-Tol) 的产率分别为 84%、94% 和 87%。该反应在没有碱的情况下进行，并给出了建议的反应机理。
• 1,2,4-Benzoxadiazines
  作者：Thomas L. Gilchrist、C. John Harris、Frank D. King、Michael E. Peek、Charles W. Rees

  DOI：10.1039/p19760002161

  日期：——

  by two new methods: (a) the reaction of N-aryl-SS-dimethylsulphimides with nitrile oxides, and (b) the oxidation of N-arylamidoximes. Both reactions are shown to involve the intermediacy of N-aryl-C-nitroso-imines, which can be reversibly intercepted in a Diels-Alder reaction with thebaine. Earlier publications on the synthesis of 1,2,4-benzoxadiazines have been re-assessed, and some of the structures

  1,2,4- Benzoxadiazines（1）已经制备由两个新方法：（一）的反应Ñ -芳基- SS -dimethylsulphimides与氧化腈，和（b）的氧化Ñ -arylamidoximes。两个反应均表明涉及的中间性Ñ -芳基- C ^亚硝基亚胺，它可与一个蒂巴因Diels-Alder反应被可逆地截获。对1,2,4-苯并恶二嗪合成的早期出版物进行了重新评估，并对先前工作人员提出的一些结构进行了修订。
• 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.