(S)-4-fluorobenzenesulfinamide | 1307296-58-7

• 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: (S)-4-fluorobenzenesulfinamide
• CAS: 1307296-58-7
• 化学式: C₆H₆FNOS
• 分子量: 159.184
• InChiKey: CGMMMJTXXAKTRV-JTQLQIEISA-N

物化性质

• 熔点：
  155-156 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  309.1±44.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-fluorobenzenesulfinamide 、 DIMETHYL TRANS-1,4-CYCLOHEXANEDICARBOXYLATE 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.5h， 生成 (trans)-N1,N4-bis((4-fluorophenyl)sulfinyl)cyclohexane-1,4-dicarboxamide
  参考文献：
  名称：

  基于 SuFEx 的构型手性聚合物

  摘要：

  使用本质手性 SuFEx（硫氟交换）点击反应来生产一系列构型手性高分子量聚合物。这种逐步增长聚合反应具有高效率和对映专一性 ( ee >98 %)。

  DOI：

  10.1002/anie.202116158
• 作为产物：
  描述：

  (S)-methyl p-fluorobenzenesulfinate 在 lithium hexamethyldisilazane 、 氯化铵 作用下， 以 甲苯 、 水 为溶剂， 反应 5.0h， 以88%的产率得到(S)-4-fluorobenzenesulfinamide
  参考文献：
  名称：

  Practical and highly stereoselective method for the preparation of several chiral arylsulfinamides and arylsulfinates based on the spontaneous crystallization of diastereomerically pure N-benzyl-N-(1-phenylethyl)-arylsulfinamides

  摘要：

  A novel and simple process for the preparation of enantiomerically pure (S(s))-benzenesulfinamide (S(s))-3a, (S(s))-p-toluenesulfinamide (S(s))-3b, (S(s))-p-chloro-benzenesulfinamide (S(s))-3c and (S(s))-p-fluorobenzenesulfinamide (S(s))-3d has been developed. The treatment of arylsulfinyl chlorides with (R)-N-benzyl-1-phenylethanamine in the presence of excess triethylamine gave diastereomeric mixtures of N-benzyl-N-(1-phenylethyl)-arylsulfinamides 1, which underwent spontaneous crystallization to furnish diastereomerically pure (R,S(s))-N-benzyl-N-(1-phenylethyl)-arylsulfinamides (R,S(s))-1a-1d in 28%, 29%, 27% and 31% yields, respectively. The diastereomerically pure compounds (R,S(s))-1 were then converted into four enantiopure (R(s))-methyl arylsulfinates (R(s))-2, and finally into four enantiopure (S(s))-arylsulfinamides (S(s))-3 in good yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.028

文献信息

• Enantioselective sulfinylation of alcohols and amines by condensation with sulfinates
  作者：Minghong Liao、Yonggui Liu、Hongyan Long、Qin Xiong、Xiaokang Lv、Zhongfu Luo、Xingxing Wu、Yonggui Robin Chi

  DOI：10.1016/j.chempr.2024.02.016

  日期：2024.3

  Achieving the preparation of enantiomerically enriched -stereogenic compounds is a long-standing objective in stereoselective synthesis, owing to the fundamental importance and broad applications of these chiral scaffolds in various fields. Despite recent significant advancements, catalyst-controlled stereoselective synthesis of -stereogenic compounds remains to be a considerable challenge, particularly

  由于这些手性支架在各个领域的根本重要性和广泛应用，实现对映体富集的立体化合物的制备是立体选择性合成的长期目标。尽管最近取得了重大进展，但催化剂控制的立体选择性合成β-立体化合物仍然是一个相当大的挑战，特别是通过小分子催化剂。在此，我们公开了一种通过形成混合亚磺酸酐来活化亚磺酸盐来对醇和胺进行高度实用和对映选择性亚磺酰化的有机催化策略。一种简单的天然奎宁催化剂通过空间拥挤部分调节反应物种的结构，有效控制亲核 S-O 和 S-N 键结构的化学和对映选择性，提供各种具有优异光学性质的手性亚磺酰基衍生物纯度。值得注意的是，该协议很容易促进与各种天然产物和商业药物的偶联，这可以为重要的生物学有趣分子的后期多样化提供有吸引力的策略。
• 10.1002/anie.202408380
  作者：Fimm, Marc、Saito, Fumito

  DOI：10.1002/anie.202408380

  日期：——

  Herein is reported an enantioselective synthesis of sulfinamidines by electrophilic amination of sulfenamides with enantiopure N−H oxaziridines. The enantioenriched sulfinamidines show remarkable chemical and configurational stability against high temperature, acids, and bases in non-aqueous solution. One-pot, three-component, enantioselective synthesis of sulfinamides is further demonstrated by employing

  本文报道了通过亚磺酰胺与对映纯 NH 恶氮丙啶的亲电胺化来对亚磺脒的对映选择性合成。对映体富集的亚磺脒在非水溶液中对高温、酸和碱表现出显着的化学和构型稳定性。通过使用对映体纯 NH 恶氮丙啶试剂，进一步证明了亚磺酰胺的一锅、三组分、对映选择性合成。
• 一种手性亚磺酰胺化合物及其制备方法和应用
  申请人：贵州大学

  公开号：CN117383995A

  公开（公告）日：2024-01-12

  本发明提供了一种手性亚磺酰胺化合物及其制备方法和应用，涉及化合物合成领域，手性亚磺酰胺化合物的结构通式如式(1)所示。本发明公开了苯亚磺酸钠和胺在催化剂奎宁或奎尼丁的催化下高效的制备手性亚磺胺化合物及其衍生物，具有优异的产率、对映选择性高达99％及良好的应用潜力和研究价值。
• Practical and highly stereoselective method for the preparation of several chiral arylsulfinamides and arylsulfinates based on the spontaneous crystallization of diastereomerically pure N-benzyl-N-(1-phenylethyl)-arylsulfinamides
  作者：Rui-Heng Zhu、Xiao-Xin Shi

  DOI：10.1016/j.tetasy.2011.01.028

  日期：2011.2

  A novel and simple process for the preparation of enantiomerically pure (S(s))-benzenesulfinamide (S(s))-3a, (S(s))-p-toluenesulfinamide (S(s))-3b, (S(s))-p-chloro-benzenesulfinamide (S(s))-3c and (S(s))-p-fluorobenzenesulfinamide (S(s))-3d has been developed. The treatment of arylsulfinyl chlorides with (R)-N-benzyl-1-phenylethanamine in the presence of excess triethylamine gave diastereomeric mixtures of N-benzyl-N-(1-phenylethyl)-arylsulfinamides 1, which underwent spontaneous crystallization to furnish diastereomerically pure (R,S(s))-N-benzyl-N-(1-phenylethyl)-arylsulfinamides (R,S(s))-1a-1d in 28%, 29%, 27% and 31% yields, respectively. The diastereomerically pure compounds (R,S(s))-1 were then converted into four enantiopure (R(s))-methyl arylsulfinates (R(s))-2, and finally into four enantiopure (S(s))-arylsulfinamides (S(s))-3 in good yields. (C) 2011 Elsevier Ltd. All rights reserved.
• Configurationally Chiral SuFEx‐Based Polymers
  作者：Dong‐Dong Liang、Sidharam P. Pujari、Muthusamy Subramaniam、Maarten Besten、Han Zuilhof

  DOI：10.1002/anie.202116158

  日期：2022.2.14

  An intrinsically chiral SuFEx (sulfur–fluorine exchange) click reaction was used to produce a series of configurationally chiral high-molecular-weight polymers. This step-growth polymerization occurs with high efficiency and enantiospecifically (ee>98 %).

  使用本质手性 SuFEx（硫氟交换）点击反应来生产一系列构型手性高分子量聚合物。这种逐步增长聚合反应具有高效率和对映专一性 ( ee >98 %)。