4-phenyl-7-methyl-1,2,3-benzoxathiazine 2,2-dioxide | 1025506-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫色烯
• 英文名称: 4-phenyl-7-methyl-1,2,3-benzoxathiazine 2,2-dioxide
• CAS: 1025506-16-4
• 化学式: C₁₄H₁₁NO₃S
• 分子量: 273.312
• InChiKey: LHBYTCCQNXVBCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.73
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-phenyl-7-methyl-1,2,3-benzoxathiazine 2,2-dioxide 在 (S,S)-f-binaphane 、 palladium(II) trifluoroacetate 、 氢气 作用下， 以 三氟乙醇 为溶剂， 25.0 ℃ 、4.14 MPa 条件下， 反应 12.0h， 以99%的产率得到4-phenyl-7-methyl-3,4-dihydro-1,2,3-benzoxathiazine 2,2-dioxide
  参考文献：
  名称：

  Enantioselective Synthesis of Cyclic Sulfamidates via Pd-Catalyzed Hydrogenation

  摘要：

  Using Pd(CF3CO2)(2)/(SS)-f-binaphane as the catalyst, an efficient enantioselective synthesis of cyclic sulfamidates was developed via asymmetric hydrogenation of the corresponding cyclic imines in 2,2,2-trifluoroethanol at room temperature with high enantioselectivities (up to 99% ee).

  DOI：

  10.1021/ol800591u
• 作为产物：
  描述：

  2-羟基-4-甲基苯甲酮 在 甲酸 、 氯磺酰异氰酸酯 、 sodium hydride 作用下， 以 N,N-二甲基乙酰胺 、 mineral oil 为溶剂， 以37%的产率得到4-phenyl-7-methyl-1,2,3-benzoxathiazine 2,2-dioxide
  参考文献：
  名称：

  Enantioselective Synthesis of Cyclic Sulfamidates via Pd-Catalyzed Hydrogenation

  摘要：

  Using Pd(CF3CO2)(2)/(SS)-f-binaphane as the catalyst, an efficient enantioselective synthesis of cyclic sulfamidates was developed via asymmetric hydrogenation of the corresponding cyclic imines in 2,2,2-trifluoroethanol at room temperature with high enantioselectivities (up to 99% ee).

  DOI：

  10.1021/ol800591u

文献信息

• Pd-catalyzed [3 + 2] cycloaddition of cyclic ketimines and trimethylenemethanes toward <i>N</i>-fused pyrrolidines bearing a quaternary carbon
  作者：Seoung-Mi Choi、Kyeong Do Kim、Jong-Un Park、Zi Xuan、Ju Hyun Kim

  DOI：10.1039/d1ra08579d

  日期：——

  A Pd-catalyzed [3 + 2] cycloaddition of N-sulfonyl cyclic ketimines and trimethylenemethanes (TMM) was developed that afforded N-fused pyrrolidines bearing a quaternary carbon. Under mild reaction conditions, structurally diverse N-sulfonyl cyclic imines, including sulfamate-fused aldimines, aryl- or styryl-substituted sulfamate-derived ketimines, and N-sulfonyl cyclic ketimines, were tolerated as

  开发了N-磺酰环酮亚胺和三亚甲基甲烷 (TMM) 的 Pd 催化 [3 + 2] 环加成反应，得到带有季碳的N-稠合吡咯烷。在温和的反应条件下，结构多样的N-磺酰环亚胺，包括氨基磺酸稠合醛亚胺、芳基或苯乙烯基取代的氨基磺酸衍生的酮亚胺和N-磺酰环酮亚胺，可以作为反应物，高效地提供N-稠合吡咯烷。
• Ir(III)/MPAA-Catalyzed Mild and Selective C–H Amidation of <i>N</i>-Sulfonyl Ketimines: Access To Benzosultam-Fused Quinazolines/Quinazolinones
  作者：Aniket Mishra、Upasana Mukherjee、Tripta Kumari Vats、Indubhusan Deb

  DOI：10.1021/acs.joc.8b00125

  日期：2018.4.6

  unprecedented mild C–H amidation for weakly coordinating cyclic N-sulfonyl ketimines, accelerated by a mono protected l-amino acid, has been developed. The method uses 1,4,2-dioxazol-5-ones as the robust amidating reagent in conjunction with a catalytic amount of silver triflate. It is highly selective and does not require a stoichiometric amount of oxidants or additives. A series of mechanistic experiments

  已经开发了Ir（III）催化的空前温和的C H H酰胺化，用于弱配位的环状N-磺酰基酮亚胺，由一个单保护的1-氨基酸促进。该方法与催化量的三氟甲磺酸银一起使用1,4,2-二恶唑-5-酮作为强力酰胺化试剂。它具有很高的选择性，不需要化学计量的氧化剂或添加剂。进行了一系列的机械实验，以获取对反应机理的一些见解。该策略可轻松获得具有药学相关功能的新型苯并舒坦-喹唑啉和苯并舒坦-喹唑啉酮杂合支架。
• Iridium-catalyzed direct C–H arylation of cyclic <i>N</i>-sulfonyl ketimines with arylsiloxanes at ambient temperature
  作者：Writhabrata Sarkar、Arup Bhowmik、Sumit Das、Aiswarya Balaram Sulekha、Aniket Mishra、Indubhusan Deb

  DOI：10.1039/d0ob01212b

  日期：——

  A highly efficient iridium-catalyzed ortho-selective C–H arylation of weakly coordinating cyclic N-sulfonyl ketimines has been achieved with environmentally benign aryl siloxanes at ambient temperature giving access to a novel class of biaryls.

  通过环境友好的芳基硅氧烷，在室温下实现了高效的铱催化的对位选择性C-H芳基化，从而获得了一类新型的联芳烃。
• The Proton of Alcohols as Hydrogen Source in Diboron-Mediated Nickel-Catalyzed Asymmetric Transfer Hydrogenation of Cyclic <i>N</i>-Sulfonyl Imines
  作者：Bo Wu、Yu-Qing Bai、Xiao-Qing Wang、Wen-Jun Huang、Yong-Gui Zhou

  DOI：10.1021/acs.joc.3c01773

  日期：2024.1.5

  The proton of alcohols as the sole hydrogen source in diboron-mediated nickel-catalyzed asymmetric transfer hydrogenation of cyclic N-sulfonyl imines has been developed, providing the chiral cyclic sulfamidates in excellent enantioselectivities. The mechanistic investigations suggested that the proton of alcohols could be activated by tetrahydroxydiboron to form active nickel hydride species.

  开发了醇质子作为二硼介导的镍催化环状N-磺酰亚胺不对称转移氢化反应中唯一氢源，提供了具有优异对映选择性的手性环状磺酰胺。机理研究表明，醇的质子可以被四羟基二硼活化，形成活性氢化镍物质。