7-methoxy-4-phenylbenzo[e][1,2,3]oxathiazine 2,2-dioxide | 4803-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 7-methoxy-4-phenylbenzo[e][1,2,3]oxathiazine 2,2-dioxide
• 英文别名: 7-Methoxy-4-phenyl-1,2lambda6,3-benzoxathiazine 2,2-dioxide；7-methoxy-4-phenyl-1,2λ6,3-benzoxathiazine 2,2-dioxide
• CAS: 4803-26-3
• 化学式: C₁₄H₁₁NO₄S
• 分子量: 289.312
• InChiKey: WNSFDFZVAUKUFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  64.96
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-methoxy-4-phenylbenzo[e][1,2,3]oxathiazine 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-methoxy-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：

  紫外线吸收剂UV-9 在 氨基磺酰氯 作用下， 生成 7-methoxy-4-phenylbenzo[e][1,2,3]oxathiazine 2,2-dioxide
  参考文献：
  名称：

  Access to Imidazolidine-Fused Sulfamidates and Sulfamides Bearing a Quaternary Center via 1,3-Dipolar Cycloaddition of Nonstabilized Azomethine Ylides

  摘要：

  A 1,3-dipolar cycloaddition reaction of nonstalpilized azomethine ylides and cyclic N-sulfonyl imines, has been developed providing a workable access to imidazolidine-fused sulfamidates, sulfamides, and benzosultams bearing a quaternary center. Distinct from the available literature, this current work enables to make entry, for the first time, into the novel imidazolidine-fused sulfamidates and sulfamides. Furthermore, the selective imidazolidine ring opening accompanied by CH2 extrusion yielded tetra-substituted sulfamidates with an aminomethyl group. In addition, imidazolidine ring opening coupled with SO2 extrusion provided synthetically useful 1,2-diamines.

  DOI：

  10.1021/acs.joc.7b00116

文献信息

• Synthesis of chiral α-substituted α-amino acid and amine derivatives through Ni-catalyzed asymmetric hydrogenation
  作者：Gongyi Liu、Xianghe Zhang、Heng Wang、Hengjiang Cong、Xumu Zhang、Xiu-Qin Dong

  DOI：10.1039/d0cc01220c

  日期：——

  developed, providing various chiral α-monosubstituted α-amino acid derivatives with excellent results (97-99% yields, 90 to >99% ee). Cyclic N-sulfonyl ketimines were also hydrogenated well to afford chiral amine derivatives with 98-99% yields and 97 to >99% ee. The gram-scale asymmetric hydrogenation was performed well with 85% yield and 99% ee using only 0.2 mol% catalyst.

  首次成功开发了高效的Ni催化的环状N-磺酰基酮亚胺基酯的不对称加氢反应，提供了各种具有优异效果的手性α-单取代α-氨基酸衍生物（97-99％的收率，90至> 99％ ee）。环状N-磺酰基酮亚胺也被充分氢化，以98-99％的收率和97至＞ 99％的ee得到手性胺衍生物。仅使用0.2mol％的催化剂，克级不对称氢化进行得很好，产率为85％，ee为99％。
• 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。