N,N-dimethyl-N'-[(4-methylphenyl)methylene]sulfamide | 586965-79-9

• 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,N-dimethyl-N'-[(4-methylphenyl)methylene]sulfamide
• 英文别名: 1-(Dimethylsulfamoyliminomethyl)-4-methylbenzene；1-(dimethylsulfamoyliminomethyl)-4-methylbenzene
• CAS: 586965-79-9
• 化学式: C₁₀H₁₄N₂O₂S
• 分子量: 226.299
• InChiKey: KOYQTFKVYKUVJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  343.8±35.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-N'-[(4-methylphenyl)methylene]sulfamide 在 氢溴酸 、 potassium carbonate 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 17.5h， 生成 4(5)-(p-tolyl)imidazole hydrobromide
  参考文献：
  名称：

  通过将甲苯磺酰基甲基异氰酸酯环化成醛亚胺来新颖合成4（5）-单取代的咪唑

  摘要：

  4（5）-单取代的咪唑（9）是通过将甲苯磺酰基甲基异氰化物（TosMIC）与N-（二甲基氨磺酰基）醛亚胺（2）或N-甲苯磺酰基亚胺（3）进行碱诱导的环加成而制备的。在第一种情况下，N-（二甲基氨磺酰基）咪唑8是初始反应产物，可以用HBr水溶液很容易地从中除去二甲基氨磺酰基。在第二种情况下，在一个操作中，1-甲苯基咪唑10的甲苯磺酰基自发地丢失，得到4（5）-单取代的咪唑9。

  DOI：

  10.1016/s0040-4020(97)00717-5
• 作为产物：
  描述：

  N,N-二甲基磺酰胺 、 对甲基苯甲醛 以 水 、 甲苯 为溶剂， 反应 16.0h， 生成 N,N-dimethyl-N'-[(4-methylphenyl)methylene]sulfamide
  参考文献：
  名称：

  P′CP′-Pincer palladium complex-catalyzed allylation of N,N-dimethylsulfamoyl-protected aldimines

  摘要：

  The P'CP'-pincer palladium complex-catalyzed allylation of N,N-dimethylsulfamoyl-protected aldimines with allyl(tributyl)stannane is investigated for the preparation of N-homoallylic sulfamides. The desired N,N-dimethylsulfamoyl-protected products are obtained in moderate to high yields in DMF under very mild conditions and a high yielding and convenient deprotection of the N,N-dimethylsulfamoyl group is also demonstrated. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.187

文献信息

• Highly Enantioselective Rh-Catalyzed Arylation of N,N-Dimethylsulfamoyl-Protected Aldimines and Cyclic N-Sulfonylimines with Chiral Phenyl Backbone Sulfoxide-Olefin Ligands
  作者：Feng Xue、Qibin Liu、Boshun Wan、Yong Zhu、Yifei Huang、Jimeng Ge

  DOI：10.1055/s-0037-1610749

  日期：2020.5

  sulfoxide-olefin ligands, a highly Rh-catalyzed addition of aryl­boronic acids to N,N-dimethylsulfamoyl-protected aldimines has been developed to afford a broad range of chiral diarylmethylamines in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). Moreover, efficient enantioselective arylation of cyclic N-sulfonylimines was also achieved with excellent enantioselectivities (up to 98% ee)

  利用基于手性2-甲氧基-1-萘亚磺酰基的苯基骨架亚砜-烯烃配体，已开发出高铑催化的芳基硼酸加成到N，N-二甲基氨磺酰基保护的醛亚胺，从而以高收率提供了广泛的手性二芳基甲胺（最高达99％）的对映选择性（最高达ee的99％）。而且，还以优异的对映选择性（高达98％ee）实现了环状N-磺酰亚胺的高效对映选择性芳基化。
• Chiral Bicyclic Bridgehead Phosphoramidite (Briphos) Ligands for Asymmetric Rhodium-Catalyzed 1,2- and 1,4-Addition
  作者：Ansoo Lee、Hyunwoo Kim

  DOI：10.1021/acs.joc.6b00033

  日期：2016.5.6

  A complementary solution for Rh-catalyzed enantioselective 1,2- and 1,4-arylation with two structurally related chiral ligands is reported. A chiral bicyclic bridgehead phosphoramidite (briphos) ligand derived from 1-aminoindane was efficient for the 1,2-arylation of N-sulfonyl imines, while that derived from 1,2,3,4-tetrahydro-1-naphthylamine was efficient for 1,4-arylation of α,β-unsaturated cyclic

  报道了具有两个结构上相关的手性配体的Rh催化对映选择性1，2-和1，4-芳基化的互补溶液。衍生自1-氨基茚满的手性双环桥头亚磷酰胺（briphos）配体对于N-磺酰基亚胺的1,2-芳基化反应有效，而衍生自1,2,3,4-四氢-1-萘胺的手性双环桥头磷酰胺则有效α，β-不饱和环酮的; 4-芳基化。对于α，β-不饱和N-甲苯磺酰基酮亚胺，发现衍生自1-氨基茚满的Briphos选择性地提供了高产率和立体选择性的γ，γ-二芳基N-甲苯磺酰基烯胺。
• Highly Enantioselective Arylation of <i>N</i>,<i>N</i>-Dimethylsulfamoyl-Protected Aldimines Using Simple Sulfur–Olefin Ligands: Access to Solifenacin and (<i>S</i>)-(+)-Cryptostyline II
  作者：Tao Jiang、Wen-Wen Chen、Ming-Hua Xu

  DOI：10.1021/acs.orglett.7b00776

  日期：2017.4.21

  With the use of a simple sulfur–olefin ligand, a highly enantioselective rhodium-catalyzed addition of arylboroxines to N,N-dimethylsulfamoyl-protected aldimines has been achieved, allowing access to a broad range of chiral diarylmethylamines in high yields (up to 98%) with uniformly excellent enantioselectivities (up to 99% ee). This catalyst system is also applicable to the arylation of N-tosyl arylimines

  通过使用简单的硫-烯烃配体，已经实现了对映体选择性铑催化的芳基硼氧烷到N，N-二甲基氨磺酰基保护的醛亚胺的加成反应，从而可以高收率获得各种手性二芳基甲胺（高达98％ ）具有一致优异的对映选择性（高达99％ee）。该催化剂体系也适用于N-甲苯磺酰基芳胺的芳基化。通过利用这种方法，可以容易地构建一些具有手性1-芳基-1,2,3,4-四氢异喹啉核心的生物活性分子，例如Solifenacin和（S）-（+）-隐香碱II。
• Improved Synthesis of β-Aminoboronate Esters via Copper-Catalyzed Diastereo- and Enantioselective Addition of 1,1-Diborylalkanes to Acyclic Arylaldimines
  作者：Jeongho Kim、Chiwon Hwang、Youngmin Kim、Seung Hwan Cho

  DOI：10.1021/acs.oprd.9b00179

  日期：2019.8.16

  scalable procedure to achieve the copper-catalyzed diastereo- and enantioselective 1,2-addition of 1,1-diborylalkanes to N-protected acyclic arylaldimines. We find that the installation of an N,N-dimethylsulfamoyl-group as N-protecting group in acyclic arylaldimines allows the 1,2-addition reaction to proceed with good-to-excellent diastereoselectivity and enantioselectivity, thus providing β-aminoboronate

  我们在本文中描述了一种改进的和可扩展的程序，以实现将铜催化的1，1-二硼烷基烷烃的非对映和对映选择性的1，2-加成至N-保护的无环芳基亚胺。我们发现N，N-二甲基氨磺酰基的安装为N无环芳基亚胺中的β-保护基团可以使1,2-加成反应以良好至优异的非对映选择性和对映选择性进行，从而以高收率提供带有邻位手性仲胺和仲硼酸酯的β-氨基硼酸酯。该反应可以轻松放大至克级（3.25克），突出了所开发方法的有用性。还证明了将所得的β-氨基硼酸酯转化为其他对映体富集的化合物的合成应用。
• Development of Binaphthyl-Based Chiral Dienes for Rhodium(I)-Catalyzed Asymmetric Arylation of <i>N</i>,<i>N</i>-Dimethylsulfamoyl-Protected Aldimines
  作者：Ziping Cao、Haifeng Du

  DOI：10.1021/ol1008087

  日期：2010.6.4

  A variety of binaphthyl-based chiral dienes were synthesized and utilized as steering ligands for the enantioselective arylation of N,N-dimethylsultamoyl-protected aldimines with arylboronic acids, and moderate to good yields and up to 84% ee were achieved.