4-(3,5-difluorophenyl)-5H-[1,2,3]-oxathiazole 2,2-dioxide | 1260403-64-2

• 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: 4-(3,5-difluorophenyl)-5H-[1,2,3]-oxathiazole 2,2-dioxide
• 英文别名: 4-(3,5-difluorophenyl)-5H-oxathiazole 2,2-dioxide
• CAS: 1260403-64-2
• 化学式: C₈H₅F₂NO₃S
• 分子量: 233.195
• InChiKey: JSBQLNWYAVOYPK-UHFFFAOYSA-N

物化性质

• 沸点：
  319.9±52.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(3,5-difluorophenyl)-5H-[1,2,3]-oxathiazole 2,2-dioxide 在 盐酸 、 (S,R)-PPF-P(t-Bu)2 、 氢气 、 palladium diacetate 、 sodium hydroxide 作用下， 以 环丁砜 、 二氯甲烷 、 水 为溶剂， 40.0~60.0 ℃ 、275.8 kPa 条件下， 反应 28.0h， 生成 (8R)-8-(3,5-difluorophenyl)-6,9-diazaspiro[4.5]decan-10-one
  参考文献：
  名称：

  Practical Asymmetric Synthesis of a Chiral Piperazinone Derivative

  摘要：

  A practical asymmetric route to a chiral piperazinone derivative, a fragment of MK-3207, is reported. The amine-bearing benzylic stereocenter is introduced via an asymmetric Pd-catalyzed hydrogenation of a cyclic sulfimidate in the presence of a chiral phosphine ligand. An efficient synthesis of the hydrogenation substrate is described, together with process development of the hydrogenation step and elaboration of the resulting cyclic sulfamate product to the desired piperazinone.

  DOI：

  10.1021/op400150w
• 作为产物：
  描述：

  1-溴-3,5-二氟苯 在 水 、 异丙基氯化镁 、 对甲苯磺酸 、 三乙胺 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 1.0h， 生成 4-(3,5-difluorophenyl)-5H-[1,2,3]-oxathiazole 2,2-dioxide
  参考文献：
  名称：

  Practical Asymmetric Synthesis of a Chiral Piperazinone Derivative

  摘要：

  A practical asymmetric route to a chiral piperazinone derivative, a fragment of MK-3207, is reported. The amine-bearing benzylic stereocenter is introduced via an asymmetric Pd-catalyzed hydrogenation of a cyclic sulfimidate in the presence of a chiral phosphine ligand. An efficient synthesis of the hydrogenation substrate is described, together with process development of the hydrogenation step and elaboration of the resulting cyclic sulfamate product to the desired piperazinone.

  DOI：

  10.1021/op400150w

文献信息

• Enantioselective Access to Chiral Cyclic Sulfamidates Through Iridium‐Catalyzed Asymmetric Hydrogenation
  作者：Yuanhua Liu、Yi Huang、Zhiyuan Yi、Gongyi Liu、Xiu‐Qin Dong、Xumu Zhang

  DOI：10.1002/adsc.201801566

  日期：2019.4

  The Iridium‐catalyzed asymmetric hydrogenation of cyclic sulfamidate imines was successfully developed with N‐methylated ZhaoPhos L2 as the ligand. A variety of chiral cyclic sulfamidates were obtained with excellent results (up to 99% yield, 99% ee). Furthermore, this asymmetric hydrogenation can be employed as the key reaction step to prepare the important intermediates in organic synthesis.

  以N-甲基化的ZhaoPhos L2为配体，成功开发了铱催化的环状氨基磺酸亚胺的不对称氢化反应。获得了多种手性环状氨基磺酸盐，具有优异的结果（产率高达99％，ee高达99％）。此外，该不对称氢化可以用作制备有机合成中重要中间体的关键反应步骤。
• Enantioselective Rh(I)-Catalyzed Addition of Arylboronic Acids to Cyclic Ketimines
  作者：Jongrock Kong、Mark McLaughlin、Kevin Belyk、Ryan Mondschein

  DOI：10.1021/acs.orglett.5b02032

  日期：2015.11.20

  A method for the enantioselective synthesis of chiral α-tertiary amines via Rh-catalyzed 1,2-addition of arylboronic acids to cyclic ketimines is described. The products are efficiently accessed in good yields and excellent enantioselectivities using a commercially available chiral ligand. The reaction scope includes vinyl, aryl, and heteroarylboronic acids with yields ranging from 40% to 99% and enantiomeric

  描述了一种通过Rh催化的将芳基硼酸加成到环酮亚胺上的1，2-加成反应，对映选择性地合成手性α-叔胺的方法。使用可商购的手性配体可有效地以高收率和优异的对映选择性获得产物。反应范围包括乙烯基，芳基和杂芳基硼酸，产率为40％至99％，对映体过量为88％至99％。还证明了加成产物转化为α，α-二芳基取代的氨基酸。
• [EN] PROCESS FOR MAKING CGRP RECEPTOR ANTAGONIST<br/>[FR] PROCÉDÉ DE PRODUCTION D'ANTAGONISTE DU RÉCEPTEUR CGRP
  申请人：MERCK SHARP & DOHME

  公开号：WO2011005731A3

  公开（公告）日：2011-05-19
• Practical Asymmetric Synthesis of a Chiral Piperazinone Derivative
  作者：Mark McLaughlin、Kevin Belyk、Cheng-yi Chen、Xin Linghu、Jun Pan、Gang Qian、Robert A. Reamer、Yingju Xu

  DOI：10.1021/op400150w

  日期：2013.8.16

  A practical asymmetric route to a chiral piperazinone derivative, a fragment of MK-3207, is reported. The amine-bearing benzylic stereocenter is introduced via an asymmetric Pd-catalyzed hydrogenation of a cyclic sulfimidate in the presence of a chiral phosphine ligand. An efficient synthesis of the hydrogenation substrate is described, together with process development of the hydrogenation step and elaboration of the resulting cyclic sulfamate product to the desired piperazinone.