(R)-3-(4-methoxyphenyl)-4-methyl-3-phenyl-2,3-dihydro-1,2,5-thiadiazole-1,1-dioxide | 1620097-60-0

• 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: (R)-3-(4-methoxyphenyl)-4-methyl-3-phenyl-2,3-dihydro-1,2,5-thiadiazole-1,1-dioxide
• CAS: 1620097-60-0
• 化学式: C₁₆H₁₆N₂O₃S
• 分子量: 316.381
• InChiKey: WVMZGLMKFYCPAJ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  67.76
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-甲氧基苯硼酸 、 3-methyl-4-phenyl-1,2,5-thiadiazole-1,1-dioxide 在 chlorobis(cyclooctene)rhodium(I) dimer 、 (R)-2-methyl-N-[2-(naphthalen-1-ylmethyl)prop-2-enyl]propane-2-sulfinamide 、 potassium fluoride 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 以53%的产率得到(R)-3-(4-methoxyphenyl)-3-methyl-4-phenyl-2,3-dihydro-1,2,5-thiadiazole-1,1-dioxide
  参考文献：
  名称：

  Rhodium-Catalyzed Highly Enantioselective Arylation of Cyclic Diketimines: Efficient Synthesis of Chiral Tetrasubstituted 1,2,5-Thiadiazoline 1,1-Dioxides

  摘要：

  A highly enantioselective rhodium-catalyzed arylation of cyclic diketimines with arylboronic acids was achieved under mild conditions by employing a simple, sulfmamide-based branched olefin ligand. This protocol provides an efficient access to valuable chiral tetrasubstituted 1,2,5-thiadiazoline 1,1-dioxides in high yields with excellent enantioselectivities of up to 99% ee.

  DOI：

  10.1021/ol501770q

文献信息

• Rh(I)-Catalyzed Enantioselective Arylation of Cyclic <i>N</i>-Sulfonyl Diketimines Using Planar-Chiral Phosphine-Olefin Ligands Based on a (Cyclopentadienyl)manganese(I) Scaffold with a Highly Fluorinated Aryl Phosphino Group
  作者：Ryosuke Shimamoto、Akihiro Tsurusaki、Ken Kamikawa

  DOI：10.1021/acs.joc.2c02930

  日期：——

  1,2,5-thiadiazoline 1,1-dioxide derivatives were achieved using planar-chiral phosphine-olefin ligand L5 with a bis[(2,3,4,5,6-pentafluoro)phenyl]phosphino group, showing ≤98% ee. The enantioselectivities of the addition products were improved by increasing the number of fluoro substituents on the aromatic ring of the ligand. X-ray crystallographic studies of 3aa and [RhCl/L5]2 revealed the absolute

  使用具有双[(2,3,4,5,6)的平面手性膦-烯烃配体L5实现了芳基硼酸与1,2,5-噻二唑啉1,1-二氧化物衍生物的催化对映选择性1,2-加成反应-五氟）苯基]膦基，显示≤98% ee。通过增加配体芳环上氟取代基的数量，提高了加成产物的对映选择性。3aa和 [RhCl/ L5 ] 2的 X 射线晶体学研究揭示了对映体富集的加成产物3的绝对构型以及L5与铑 (I) 阳离子的膦-烯烃二齿配位模式。