N-butyl-S-methyl-S-phenylsulfoximine

• 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-butyl-S-methyl-S-phenylsulfoximine
• 英文别名: Butylimino-methyl-oxo-phenyl-lambda6-sulfane；butylimino-methyl-oxo-phenyl-λ6-sulfane
• 化学式: C₁₁H₁₇NOS
• 分子量: 211.328
• InChiKey: PXZRHVCJFMXVOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-butyl-S-methyl-S-phenylsulfoximine 在 盐酸 、 叔丁基过氧化氢 、 甲酸 、 水 、 1-羟基苯并三唑 、 iron(II) chloride 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 182.0h， 生成 N-(4-methylbenzoyl)-S-methyl-S-phenylsulfoximine
  参考文献：
  名称：

  N-烷基亚砜亚胺的铁催化酰基化脱烷基化

  摘要：

  由于我们最近对亚砜亚胺的 N-官能化的研究，开发了一种铁催化的 N-烷基亚砜亚胺的脱烷基酰化。该方法涉及 N-烷基化亚砜亚胺的 Polonovski 型脱烷基化，以提供反应性中间体，该中间体在合适的醛或酸酐存在下被捕获，以在一锅中提供 N-酰基-和 N-芳酰基亚砜亚胺衍生物。随后在酸性条件下裂解酰基或芳酰基会产生具有合成价值的 NH-亚砜亚胺。

  DOI：

  10.1002/ejoc.201500855
• 作为产物：
  描述：

  在 potassium permanganate 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以68 mg的产率得到N-butyl-S-methyl-S-phenylsulfoximine
  参考文献：
  名称：

  Direct Access to N-Alkylsulfoximines from Sulfides by a Sequential Imidation/Oxidation Procedure

  摘要：

  Synthetically relevant N-alkyl-substituted sulfoximines are directly prepared from sulfides by an unprecedented one-pot imidation/oxidation sequence. In situ generated N-bromoalkylamines serve as readily accessible imidating agents leading to N-alkylsulfiliminium bromides that are subsequently oxidized providing the corresponding N-alkylsulfoximines. In this manner, gram quantities of the products can be obtained in a short period of time avoiding the use of toxic and cumbersome to handle alkylating reagents.

  DOI：

  10.1055/s-0034-1380536

文献信息

• <i>N</i>-Alkylations of<i>N</i>H-Sulfoximines and<i>N</i>H-Sulfondiimines with Alkyl Halides Mediated by Potassium Hydroxide in Dimethyl Sulfoxide
  作者：Christine M. M. Hendriks、Rebekka A. Bohmann、Marina Bohlem、Carsten Bolm

  DOI：10.1002/adsc.201400193

  日期：2014.5.26

  A general method for the N‐alkylation of NH‐sulfoximines and NH‐sulfondiimines has been developed, employing alkyl bromides with KOH in DMSO at room temperature. A variety of previously inaccessible N‐alkylated sulfoximines and sulfondiimines was prepared in good to excellent yields (up to 97%). As an application, the conditions were used to access the biologically active Suloxifen.

  对于一般方法Ñ的烷基化Ñ H-亚磺酰亚胺和Ñ H-sulfondiimines已经开发，采用用KOH烷基溴化物在DMSO在室温下。制备了许多以前无法获得的N烷基化亚砜亚砜和磺二亚胺，收率高达97％。作为应用，使用条件来获得具有生物活性的舒洛昔芬。
• Alkylation of sulfoximine and related compounds at the imino nitrogen under phase-transfer conditions
  作者：Carl R. Johnson、Olivier M. Lavergne

  DOI：10.1021/jo00059a052

  日期：1993.3
• JOHNSON, C. R.;BIS, K. G.;CANTILLO, J. H.;MEANWELL, N. A.;REINHARD, M. F.+, J. ORG. CHEM., 1983, 48, N 1, 1-3
  作者：JOHNSON, C. R.、BIS, K. G.、CANTILLO, J. H.、MEANWELL, N. A.、REINHARD, M. F.+

  DOI：——

  日期：——
• Direct Access to N-Alkylsulfoximines from Sulfides by a Sequential Imidation/Oxidation Procedure
  作者：Vincent Bizet、Carsten Bolm、Carl Dannenberg

  DOI：10.1055/s-0034-1380536

  日期：——

  Synthetically relevant N-alkyl-substituted sulfoximines are directly prepared from sulfides by an unprecedented one-pot imidation/oxidation sequence. In situ generated N-bromoalkylamines serve as readily accessible imidating agents leading to N-alkylsulfiliminium bromides that are subsequently oxidized providing the corresponding N-alkylsulfoximines. In this manner, gram quantities of the products can be obtained in a short period of time avoiding the use of toxic and cumbersome to handle alkylating reagents.
• Iron-Catalyzed Acylative Dealkylation of<i>N</i>-Alkylsulfoximines
  作者：Philip Lamers、Daniel L. Priebbenow、Carsten Bolm

  DOI：10.1002/ejoc.201500855

  日期：2015.9

  As a result of our recent investigations into the N-functionalization of sulfoximines, an iron-catalyzed dealkylative acylation of N-alkylsulfoximines has been developed. This process involves a Polonovski-type dealkylation of an N-alkylated sulfoximine to afford a reactive intermediate that is trapped in the presence of a suitable aldehyde or anhydride to afford N-acyl- and N-aroylsulfoximine derivatives

  由于我们最近对亚砜亚胺的 N-官能化的研究，开发了一种铁催化的 N-烷基亚砜亚胺的脱烷基酰化。该方法涉及 N-烷基化亚砜亚胺的 Polonovski 型脱烷基化，以提供反应性中间体，该中间体在合适的醛或酸酐存在下被捕获，以在一锅中提供 N-酰基-和 N-芳酰基亚砜亚胺衍生物。随后在酸性条件下裂解酰基或芳酰基会产生具有合成价值的 NH-亚砜亚胺。