(S)-3-benzyl-7-bromo-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepine-1,1-dioxide | 1257313-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-benzyl-7-bromo-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepine-1,1-dioxide
• 英文别名: (3S)-3-benzyl-7-bromo-3,4-dihydro-2H-5,1lambda6,2-benzoxathiazepine 1,1-dioxide；(3S)-3-benzyl-7-bromo-3,4-dihydro-2H-5,1λ6,2-benzoxathiazepine 1,1-dioxide
• CAS: 1257313-63-5
• 化学式: C₁₅H₁₄BrNO₃S
• 分子量: 368.251
• InChiKey: BHDLZPJXKWGQPM-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-benzyl-7-bromo-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepine-1,1-dioxide 、 (3S,4R)-7-fluoro-3-methyl-4-phenyl-3,4-dihydro-2H-5,1lambda6,2-benzoxathiazepine 1,1-dioxide 在 caesium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以85%的产率得到(3S)-3-benzyl-7-bromo-2-[[1-[(3-chlorophenyl)methyl]triazol-4-yl]methyl]-3,4-dihydro-5,1lambda6,2-benzoxathiazepine 1,1-dioxide
  参考文献：
  名称：

  Facile (Triazolyl)methylation of MACOS-derived Benzofused Sultams Utilizing ROMP-derived OTP Reagents

  摘要：

  A combination of MACOS scale-out and ROMP-derived oligomeric triazole phosphates (OTPn) have been successfully utilized for the preparation of a 106-member library of triazole containing benzothiaoxazepine-1,1-dioxides. This report demonstrates the utilization of a suite of soluble OTPn reagents for facile (triazolyl)methylation of 10 MACOS-derived sultam scaffolds in purification-free process for parallel synthesis of small molecule collections for HTS.

  DOI：

  10.1021/co2001839
• 作为产物：
  描述：

  4-bromo-2-fluoro-N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]benzenesulfonamide 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以85%的产率得到(S)-3-benzyl-7-bromo-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepine-1,1-dioxide
  参考文献：
  名称：

  通过微波辅助连续流动有机合成 (MACOS) 进行放大：溴-和氟-苯并稠合的 Sultams Benzthiaoxazep​​ine-1,1-dioxides 的多克合成

  摘要：

  顺其自然！使用连续流技术和微波辐射的组合，已经生产了 5-10 克数量的 benzthiaoxazep​​ine-1,1-dioxides 的 19 个成员集合（见方案）。通过调用横向扩展（而不是纵向扩展）的概念来消除中大规模工艺优化，从而显着减少了制备这些化合物所需的时间。

  DOI：

  10.1002/chem.201001651

文献信息

• Synthesis of High-Load, Hybrid Silica-Immobilized Heterocyclic Benzyl Phosphate (Si–OHBP) and Triazolyl Phosphate (Si–OHTP) Alkylating Reagents
  作者：Saqib Faisal、Pradip K. Maity、Qin Zang、Alan Rolfe、Paul R. Hanson

  DOI：10.1021/acscombsci.6b00042

  日期：2016.7.11

  The development of new ROMP-derived silica-immobilized heterocyclic phosphate reagents and their application in purification-free protocols is reported. Grafting of norbornenyl norbornenyl-functionalized (Nb-tagged) silica particles with functionalized Nb-tagged heterocyclic phosphate monomers efficiently yield high-load, hybrid silica-immobilized oligomeric heterobenzyl phosphates (Si–OHBP) and heterotriazolyl

  报道了新的ROMP衍生的二氧化硅固定的杂环磷酸盐试剂的开发及其在无纯化方案中的应用。用功能化的Nb标签的杂环磷酸酯单体接枝降冰片烯降冰片烯官能化的（Nb标签）二氧化硅颗粒可有效产生高负载的杂化二氧化硅固定的低聚杂苄基磷酸酯（Si–OHBP）和杂三唑基磷酸酯（Si–OHTP）作为有效的烷基化反应代理商。这些试剂用于N-，O-和S-亲核物种多样化，有效进行杂苄基化和杂（三唑基）甲基化的应用已得到验证。
• Silica-Supported Oligomeric Benzyl Phosphate (Si-OBP) and Triazole Phosphate (Si-OTP) Alkylating Reagents
  作者：Pradip K. Maity、Saqib Faisal、Alan Rolfe、Diana Stoianova、Paul R. Hanson

  DOI：10.1021/acs.joc.5b01456

  日期：2015.10.16

  The syntheses of silica-supported oligomeric benzyl phosphates (Si-OBPn) and triazole phosphates (Si-OTPn) using ring-opening metathesis polymerization (ROMP) for use as efficient alkylating reagents is reported. Ease of synthesis and grafting onto the surface of norbornenyl-tagged (Nb-tagged) silica particles has been demonstrated for benzyl phosphate and triazole phosphate monomers. It is shown that these silica polymer hybrid reagents, Si-OBPn and Si-OTPn, can be used to carry out alkylation reactions with an array of different nudeophiles to afford the corresponding benzylated and (triazolyl)methylated products in good yield and high purity.
• Scaling Out by Microwave-Assisted, Continuous Flow Organic Synthesis (MACOS): Multi-Gram Synthesis of Bromo- and Fluoro-benzofused Sultams Benzthiaoxazepine-1,1-dioxides
  作者：Farman Ullah、Thiwanka Samarakoon、Alan Rolfe、Ryan D. Kurtz、Paul R. Hanson、Michael G. Organ

  DOI：10.1002/chem.201001651

  日期：——

  Go with the flow! Using a combination of continuous‐flow techniques and microwave irradiation, a 19‐member collection of 5–10 gram quantities of benzthiaoxazepine‐1,1‐dioxides has been produced (see scheme). The elimination of intermediate‐ and large‐scale process optimization by invoking the concept of scale‐out (rather than scale up) has significantly reduced the time necessary to prepare these compounds

  顺其自然！使用连续流技术和微波辐射的组合，已经生产了 5-10 克数量的 benzthiaoxazep​​ine-1,1-dioxides 的 19 个成员集合（见方案）。通过调用横向扩展（而不是纵向扩展）的概念来消除中大规模工艺优化，从而显着减少了制备这些化合物所需的时间。
• Facile (Triazolyl)methylation of MACOS-derived Benzofused Sultams Utilizing ROMP-derived OTP Reagents
  作者：Saqib Faisal、Farman Ullah、Pradip K. Maity、Alan Rolfe、Thiwanka B. Samarakoon、Patrick Porubsky、Benjamin Neuenswander、Gerald H. Lushington、Fatima Z. Basha、Michael G. Organ、Paul R. Hanson

  DOI：10.1021/co2001839

  日期：2012.4.9

  A combination of MACOS scale-out and ROMP-derived oligomeric triazole phosphates (OTPn) have been successfully utilized for the preparation of a 106-member library of triazole containing benzothiaoxazepine-1,1-dioxides. This report demonstrates the utilization of a suite of soluble OTPn reagents for facile (triazolyl)methylation of 10 MACOS-derived sultam scaffolds in purification-free process for parallel synthesis of small molecule collections for HTS.