p-toluenesulfonyl-N-trimethylsilylamine | 1015-42-5

• 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: p-toluenesulfonyl-N-trimethylsilylamine
• 英文别名: 4-methyl-N-(trimethylsilyl)benzenesulfonamide；N-Trimethylsilyl-p-tosylamid；N-Trimethylsilyl-p-toluolsulfonamid；N--toluol-4-sulfonamid；4-Methylbenzenesulfonamide, N-trimethylsilyl-；4-methyl-N-trimethylsilylbenzenesulfonamide
• CAS: 1015-42-5
• 化学式: C₁₀H₁₇NO₂SSi
• 分子量: 243.402
• InChiKey: KPNVQKJPVNHKBT-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77 °C
• 沸点：
  127-129 °C(Press: 0.013 Torr)
• 密度：
  1.081±0.06 g/cm3(Predicted)
• 保留指数：
  1788

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  p-toluenesulfonyl-N-trimethylsilylamine 在 碘苯二乙酸 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 、 正戊烷 为溶剂， 生成 4-methyl-N-(2-oxocyclohexyl)benzenesulfonamide
  参考文献：
  名称：

  通过具有高价碘试剂的Umpolung对酮进行灵活的立体选择性官能化

  摘要：

  由于此类产品具有广泛的生物学重要性，因此羰基化合物在α位上的功能化作为合成途径已引起广泛关注。通过极性反转或“极性”，我们在这里表明典型的亲核试剂，例如氧，氮，甚至碳亲核试剂，在将它们束缚到烯醇醚后，可以用于加成反应。我们的发现可以进行新颖的逆合成规划，并可以快速组装以前只能通过多步序列访问的结构。

  DOI：

  10.1002/anie.201400405
• 作为产物：
  描述：

  对甲苯磺酰氯 、 六甲基二硅氮烷 反应 2.0h， 以73%的产率得到p-toluenesulfonyl-N-trimethylsilylamine
  参考文献：
  名称：

  Synthesis, Characterization, and Theoretical Analysis of Soluble Poly(oxothiazenes): The Ambient Temperature Lewis Acid Catalyzedin SituPolymerization ofN-Silylsulfonimidoyl Chlorides

  摘要：

  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.

  DOI：

  10.1021/ma302424u

文献信息

• Hexamethyldisilazane-Mediated Amidination of Sulfonamides and Amines with Formamides
  作者：Yu-Chen Chou、Wei-Han Lin、Xiu-Yi Lin、Chin-Ling Kuo、Wan-Qin Zeng、I-Chung Lu、Chien-Fu Liang

  DOI：10.1021/acs.joc.2c01902

  日期：2022.11.18

  Hexamethyldisilazane was reacted with formamides to generate N,N-disubstituent formimidamide, after which a reaction with sulfonamides was induced to form sulfonylformamidines. This protocol can be applied for arylformamidine formation in which anilines are used as substrates under optimized conditions. The advantages of this method are high efficiency, structural diversity in products with good yields

  六甲基二硅氮烷与甲酰胺反应生成N , N-二取代基甲酰亚胺，然后与磺酰胺反应生成磺酰甲脒。该协议可应用于芳基甲脒形成，其中苯胺在优化条件下用作底物。该方法的优点是效率高，产品结构多样，产率高，适用于大规模操作。
• Synthesis of 1,3-Dichloro-<i>cyclo</i>-1,3-diphosphadiazanes from Silylated Amino(dichloro)phosphanes
  作者：Axel Schulz、Alexander Villinger、Andrea Westenkirchner

  DOI：10.1021/ic4017728

  日期：2013.10.7

  The synthesis of 1,3-dichloro-cyclo-1,3-diphosphadiazanes [ClP(mu-NR)](2) via elimination of Me3SiCl from silylated amino(dichloro)phosphanes, R-N(SiMe3)PCl2, was studied by different synthetic protocols starting from R-N(H)SiMe3 (R = Si(SiMe3)(3) = Hyp, N(SiMe3)(2), Mes* = 2,4,6-tri-tert-butylphenyl, Ter = 2,4-bis(2,4,6-trimethylphenyl)phenyl, Dipp = 2,6-diisopro-pylphenyl, Dmp = 2,6-dimethylphenyl, Ad = Adamantyl, Trityl = Ph3C, Tos = tosyl = CH3C6H4SO2, n-Oct = n-octyl, and Me3Si).A new synthetic route using trimethylsilyl-substituted amino(dichloro)phosphanes, R-N(SiMe3)PCl2, was developed to form cyclo-diphosph(III)-azanes simply by adding a mixture of RfOH/base (RfOH = hexafluoroisopropanole). By this method electron-rich/-poor aryl-, silyl-, and bissilylamino-substituted cyclo-diphosph(III)-azanes are accessible such as the unprecedented (Me3Si)(2)N-substituted species [ClP(mu-NN(SiMe3)(2))](2) starting from tris(trimethylsilyl)hydrazine and PCl3. Additionally, the difficulties with the preparation of cyclo-diphosphadiazanes depending on the starting materials, solvents, and bases due to the competition of different reaction channels are studied.
• 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：——
• Nonbenzamidine acylsulfonamide tissue factor–factor VIIa inhibitors
  作者：Peter W. Glunz、Xiaojun Zhang、Yan Zou、Indawati Delucca、Alexandra H. Nirschl、Xuhong Cheng、Carolyn A. Weigelt、Daniel L. Cheney、Anzhi Wei、Rushith Anumula、Joseph M. Luettgen、Alan R. Rendina、Mark Harpel、Gang Luo、Robert Knabb、Pancras C. Wong、Ruth R. Wexler、E. Scott Priestley

  DOI：10.1016/j.bmcl.2013.06.027

  日期：2013.9

  Aminoisoquinoline and isoquinoline groups have successfully replaced the more basic P1 benzamidine group of an acylsulfonamide factor Vila inhibitor. Inhibitory activity was optimized by the identification of additional hydrophobic and hydrophilic P' binding interactions. The molecular details of these interactions were elucidated by X-ray crystallography and molecular modeling. We also show that decreasing the basicity of the P1 group results in improved oral bioavailability in this chemotype. (C) 2013 Elsevier Ltd. All rights reserved.
• Flexible Stereoselective Functionalizations of Ketones through Umpolung with Hypervalent Iodine Reagents
  作者：Pushpak Mizar、Thomas Wirth

  DOI：10.1002/anie.201400405

  日期：2014.6.2

  The functionalization of carbonyl compounds in the α‐position has gathered much attention as a synthetic route because of the wide biological importance of such products. Through polarity reversal, or “umpolung”, we show here that typical nucleophiles, such as oxygen, nitrogen, and even carbon nucleophiles, can be used for addition reactions after tethering them to enol ethers. Our findings allow novel

  由于此类产品具有广泛的生物学重要性，因此羰基化合物在α位上的功能化作为合成途径已引起广泛关注。通过极性反转或“极性”，我们在这里表明典型的亲核试剂，例如氧，氮，甚至碳亲核试剂，在将它们束缚到烯醇醚后，可以用于加成反应。我们的发现可以进行新颖的逆合成规划，并可以快速组装以前只能通过多步序列访问的结构。