N-氰甲基-4-甲基苯磺酰胺 | 20228-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-氰甲基-4-甲基苯磺酰胺
• 英文名称: N-(cyanomethyl)-(4-methylphenyl)sulfonamide
• 英文别名: N-(cyanomethyl)-4-methylbenzenesulfonamide；N-(p-toluenesulfonyl)aminoacetonitrile；(tosylamido)acetonitrile；N-(toluene-4-sulfonyl)-glycine nitrile；N-(Toluol-4-sulfonyl)-glycin-nitril；N-cyanomethyl-4-methyl-benzenesulfonamide
• CAS: 20228-87-9
• 化学式: C₉H₁₀N₂O₂S
• mdl: MFCD00461012
• 分子量: 210.257
• InChiKey: KOOBRRKKRKKSMZ-UHFFFAOYSA-N

物化性质

• 熔点：
  136 °C
• 沸点：
  383.8±52.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  78.3
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2935009090
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  N-氰甲基-4-甲基苯磺酰胺 在 hafnium tetrakis(trifluoromethanesulfonate) 、 三甲基氯硅烷 、 三苯基膦 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 methyl 3-amino-5-(phenylsulfanyl)-1-(p-toluenesulfonyl)-2,7-dihydro-1H-azepine-4-carboxylate
  参考文献：
  名称：

  Synthesis of Azepines via a [6 + 1] Annulation of Ynenitriles with Reformatsky Reagents

  摘要：

  A protocol for the direct synthesis of azepines using a hafnium(III)-catalyzed [6 + 1] annulation of N-tethered ynenitriles with Reformatsky reagents is reported. A broad range of 3-amino-2,7-dihydro-1H-azepine-4-carboxylates 4aa-4he were obtained in high yields and with excellent functional group tolerance. The copper-mediated reactions of isolable Blaise intermediates (enamino esters 3), uniquely underwent beta-endo cydization to afford the beta-2,5-dihydropyrrolyl alpha,beta-unsaturated esters 5aa-5fc, which exhibit anticancer activity.

  DOI：

  10.1021/acs.joc.5b01397
• 作为产物：
  描述：

  N-甲基对甲苯磺酰胺 在 sodium hydride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.5h， 生成 N-氰甲基-4-甲基苯磺酰胺
  参考文献：
  名称：

  磺酰胺类无过渡金属的αCsp3-H氰化

  摘要：

  该报告描述了通过亚胺中间体的现场生成对磺酰胺衍生物进行的位点选择性α-官能化。可以促进消除反应生成亚胺的Nf磺酰胺与TBACN偶联，可有效，温和地提供α-氨基氰化物。与Strecker反应相比，这种转化提供了一种补充策略，可以从磺酰胺的直接αC-H官能化有效地构建α-氨基氰化物。该反应的特征还在于广泛的底物范围和无需快速色谱柱的后处理。更重要的是，通过控制离去基团产生亚胺的新的双电子途径使我们获得了出色的α位选择性。

  DOI：

  10.1002/chem.202100902

文献信息

• Gold(I)-Catalyzed Enantioselective Intramolecular Dehydrative Amination of Allylic Alcohols with Carbamates
  作者：Paramita Mukherjee、Ross A. Widenhoefer

  DOI：10.1002/anie.201107877

  日期：2012.2.6

  Aliphatic nitrogen heterocycles—either five‐ or six‐membered—are formed in high yield and with up to 94 % ee when a 1:2 mixture of [(S)‐2](AuCl)2 and AgClO4 is used as the catalyst for the title reaction.

  当 [( S )- 2 ](AuCl) 2和 AgClO 4的 1:2 混合物用作催化剂时，可以高产率地形成脂肪族氮杂环（五元或六元），ee高达 94% 为标题反应。
• N-ACYLATED AMINO ACID IMINO CHLORIDES AND A QUALITATIVE STUDY OF RING CLOSURE AMONG N-ACYLAMINO ACID CHLORIDES
  作者：Edward Ronwin

  DOI：10.1139/v57-140

  日期：1957.9.1

  Products have been isolated from the treatment of N-acylaminoacetonitriles with dry hydrogen chloride which are either the open-chain imino acid chlorides or the dissociated salt forms. These compound types have often been postulated as reaction intermediates but never isolated with an unsubstituted nitrogen atom. In the unsubstituted condition they are analogous to regular or oxygen acid chlorides.Several N-acylamino acids were treated with PCl₅ and the reaction solutions were subjected to infrared spectral analyses. The results indicate that the open-chain acid chloride, rather than the azlactone salt, is the predominant product obtained with the compounds used in this investigation.

  产品已经从N-酰氨基乙腈与干氯化氢的处理中分离出来，这些产品是开链亚氨基酸氯化物或解离的盐形式。这些化合物类型经常被假设为反应中间体，但从未与未取代的氮原子分离出来。在未取代的条件下，它们类似于常规或氧酸氯化物。几种N-酰氨基酸被PCl5处理，反应溶液经过红外光谱分析。结果表明，在这项研究中使用的化合物中，开链酸氯化物而不是氮内酯盐是主要产物。
• Photoredox Transformations with Dimeric Gold Complexes
  作者：Guillaume Revol、Terry McCallum、Mathieu Morin、Fabien Gagosz、Louis Barriault

  DOI：10.1002/anie.201306727

  日期：2013.12.9

  Let the sunshine in! Unactivated alkyl and aryl bromides underwent a light‐enabled reductive radical cyclization in the presence of a dimeric phosphine–gold complex as a photocatalyst (see scheme; X=C(CO2Et)2, NR, O). Sunlight can be used as the energy source for this simple and efficient radical reaction, which does not require potentially hazardous and toxic chemical reagents, such as organostannanes

  让阳光照进来！未活化的烷基和芳基溴化物在二聚膦-金络合物作为光催化剂的情况下进行了光活化的还原性自由基环化反应（见方案； X = C（CO 2 Et）2，NR，O）。阳光可以用作此简单有效的自由基反应的能源，该自由基反应不需要潜在危险和有毒的化学试剂，例如有机锡和化学引发剂。
• The iron-catalyzed construction of 2-aminopyrimidines from alkynenitriles and cyanamides
  作者：Timothy K. Lane、Minh H. Nguyen、Brendan R. D'Souza、Nathan A. Spahn、Janis Louie

  DOI：10.1039/c3cc44422h

  日期：——

  Several cycloaddition catalysts and reagents were surveyed for their effectiveness toward cyclizing alkynenitriles with cyanamides. Catalytic amounts of FeI2, iPrPDAI and Zn were found to effectively catalyze the [2+2+2] cycloaddition of a variety of cyanamides and alkynenitriles to afford bicyclic 2-aminopyrimidines.

  研究了多种环加成催化剂和试剂对于含氰基炔烃与氰胺环化反应的催化效果。发现催化量的FeI2、iPrPDAI和Zn能有效催化多种氰胺与含氰基炣烃的[2+2+2]环加成反应，得到双环的2-氨基嘧啶。
• Studies on Hepatic Agents. I. Synthesis of Aminoacyl (and Hydroxyacyl) Aminoacetonitriles
  作者：SEIGO SUZUE、TUTOMU IRIKURA

  DOI：10.1248/cpb.16.1417

  日期：——

  For the purpose of elucidating the structural relationship between lathyrism and inhibition of necrosis induced by CCl4 in the liver of the rat, many compounds related to aminoacetonitrile were synthesized. N-Aminoacylaminoacetonitriles (VIII, XIV) were synthesized from phthaloylaminoacylaminoacetonitriles. VIII were converted to 2-hydroxyimino-5-oxopiperazine derivatives (XV) and 5-oxo-2-thio-piperazines (XX). Preparations of N-(N-acylaminoacyl) aminoacetonitriles were also described. Further, N-α-hydroxyacylaminoacetonitriles were prepared from chloralides of α-hydroxyacids with aminoacetonitrile. In addition, XV (R=H) was converted to 2-acetamino-5-acetoxypyrazine by treatment with acetic anhydride.

  为了阐明贻贝症与四氯化碳诱导的大鼠肝脏坏死抑制之间的结构关系，合成了许多与氨基乙腈相关的化合物。N-氨基酰氨基乙腈（VIII，XIV）是从邻苯二甲酰氨基酰氨基乙腈合成的。VIII被转化为2-羟基亚胺-5-氧杂哌嗪衍生物（XV）和5-氧-2-硫杂哌嗪（XX）。还描述了N-(N-酰氨基酰)氨基乙腈的制备。此外，N-α-羟基酰氨基乙腈是由α-羟基酸的氯化物与氨基乙腈反应制备的。此外，通过用醋酸无水物处理，XV（R=H）被转化为2-乙酰氨基-5-乙酰氧基吡唑。