N-(trimethylsilyl)methanesulfonamide | 999-96-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-(trimethylsilyl)methanesulfonamide
• 英文别名: N-(Trimethylsilyl)-methansulfonamid；Methanesulfonamide, N-(trimethylsilyl)-；N-trimethylsilylmethanesulfonamide
• CAS: 999-96-2
• 化学式: C₄H₁₃NO₂SSi
• 分子量: 167.304
• InChiKey: HLBXKJQKDUEWCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(trimethylsilyl)methanesulfonamide 在 水 作用下， 生成 甲基磺酰胺
  参考文献：
  名称：

  Darstellung und Eigenschaften von Trimethyl-(dialkylamidosulfonyl)-ammoniumhalogeniden

  摘要：

  DOI：

  10.1007/bf00911403
• 作为产物：
  描述：

  甲基磺酰氯 、 六甲基二硅氮烷 反应 2.0h， 以94%的产率得到N-(trimethylsilyl)methanesulfonamide
  参考文献：
  名称：

  Roy, Aroop K., Journal of the American Chemical Society, 1993, vol. 115, # 7, p. 2598 - 2601

  摘要：

  DOI：

文献信息

• Unusual C–H Bond Activation and C(sp³)–C(sp³) Bond Formation at an Fe(II) Bis(amide) Carbene Complex
  作者：Anthony Wong、Kevin Guevara、Guang Wu、Gabriel Ménard

  DOI：10.1021/acs.organomet.9b00674

  日期：2020.1.13

  Treatment of (IMes)Fe(NTMS2)2 with 4 equiv of methanesulfonyl chloride (MsCl = MeSO2Cl) resulted in a complex reaction sequence involving substitution of two TMS groups for Ms, followed by the unexpected C(sp3)–H bond activation of Ms and subsequent C(sp3)–C(sp3) bond formation to generate the bimetallic Fe complex, [IMesH]2[Cl2Fe(N(TMS)SO2(CH2)2SO2N(TMS))2FeCl2] (1) (IMes = 1,3-bis(2,4,6-trimethylphenyl)-

  用4当量的甲磺酰氯（MsCl = MeSO 2 Cl）处理（IMes）Fe（NTMS 2）2导致复杂的反应序列，涉及用两个TMS基团取代Ms，然后是意外的C（sp 3）–H Ms的键活化和随后的C（sp 3）–C（sp 3）键形成，以生成双金属Fe络合物[IMesH] 2 [Cl 2 Fe（N（TMS）SO 2（CH 2）2 SO 2 N（ TMS））2 FeCl 2 ]（1）（IMes = 1,3-双（2,4,6-三甲基苯基）-咪唑-2-亚烷基； TMS = SiMe 3）。将此C–H活化/ CC键形成化学反应扩展至较大的烷基磺酰氯链（即Et和Bu）类似地导致C–C偶联，但降低了化学选择性。为了阐明这种以前未知的C（sp 3）–C（sp 3）键形成途径的统一机制，进行了详细的机械研究，包括使用可能的中间模型化合物。
• Silylation process
  申请人：Gist-Brocades N.V.

  公开号：US04400509A1

  公开（公告）日：1983-08-23

  An improved process for the trimethylsilylation of organic compounds with at least one active hydrogen atom with hexamethyldisilazane, the improvement comprising effecting the reaction in the presence of 0.001 to 10 mole percent of a catalyst of the formula X--NH--Y I wherein X and Y are individually an electron-withdrawing group or when X is an electron-withdrawing group, Y is selected from the group consisting of hydrogen and trialkylsilyl of 1 to 6 carbon atoms or X and Y together with the nitrogen atom to which they are attached form a cyclic electron-withdrawing group and novel trimethylsilylated thiols of the formula ##STR1## wherein R is a 5-or 6-membered heterocycle having at least one nitrogen or sulfur heteroatom and optionally substituted with at least one member of the group consisting of alkyl of 1 to 6 carbon atoms, phenyl, trimethylsilyl, trimethylsilyloxycarbonylmethyl and alkylamino of 1 to 6 carbon atoms, and novel trimethylsilylated 3'-substituted cephalosporanic acid derivatives.

  使用六甲基二硅氨基对至少含有一个活性氢原子的有机化合物进行三甲基硅基化的改进方法，其中改进包括在0.001到10摩尔％的催化剂存在下进行反应，所述催化剂的公式为X-NH-Y I，其中X和Y分别是电子吸引基团，或当X是电子吸引基团时，Y选自由1至6个碳原子的三烷基硅基或X和Y与它们附着的氮原子一起形成环状电子吸引基团；以及具有以下公式的新型三甲基硅基化硫醇：##STR1## 其中R是至少含有一个氮或硫杂原子的5或6成员杂环，并且可选择地被1至6个碳原子的烷基，苯基，三甲基硅基，三甲基硅氧羰基甲基和1至6个碳原子的烷基氨基中的一个成员取代，以及新型的三甲基硅基化3'-取代头孢菌素酸衍生物。
• Catalysts for silylations with 1,1,1,3,3,3-hexamethyldisilazane
  作者：Cornelis A. Bruynes、Theodorus K. Jurriens

  DOI：10.1021/jo00141a031

  日期：1982.9
• Synthesis, Characterization, and Theoretical Analysis of Soluble Poly(oxothiazenes): The Ambient Temperature Lewis Acid Catalyzed<i>in Situ</i>Polymerization of<i>N</i>-Silylsulfonimidoyl Chlorides
  作者：Victoria Aldeva、Sossina Gezahegn、Babak Panahi、Michelle Shuoprasad、Jon Ward、Daniel A. Foucher、Robert A. Gossage、Andrew R. McWilliams

  DOI：10.1021/ma302424u

  日期：2013.4.9

  The ambient temperature condensation, to yield low molecular weight poly(methyloxothiazene) (M-w = 1 x 10(4); PDI = 1.4), can be achieved by the reaction of MeS(O-2)NHSiMe3 and SOCl2-this latter reaction being performed in an attempt to isolate ClSMe(O)NSiMe3 (6a). The in situ addition of a Lewis acid initiator (e.g., PCl5) to freshly prepared samples of N-silylsulfonimidoyl chlorides (ClSR(O)NSiMe3, 6a-d, R = Me, Et, Ph, p-C6H4Me) yielded high molecular weight, narrowly dispersed polymers, 5a-d (M-w = 6.7 x 10(4)-3.3 x 10(6); PDI = 1.2-1.6) of general formula [RS(O)=N](n). These materials have been characterized by GPC, NMR (H-1, C-13) spectroscopy, and DSC. UV-vis spectroscopy of CH2Cl2 solutions of 5a-d reveal a high-energy pi-pi* transition (lambda(max) = 300-350 nin) that tails into the visible. Additionally, theoretical modeling of oligomeric (rnethyloxothiazenes) at either a semiempirical, Hartree-Fock, or DFT level of theory suggests that these polymers adopt an irregular helical architecture.
• Derkach,N.Ya.; Smetankina,N.P., Journal of general chemistry of the USSR, 1964, vol. 34, p. 3660 - 3662
  作者：Derkach,N.Ya.、Smetankina,N.P.

  DOI：——

  日期：——