(S)-2-chlorotetrafluoroethanesulfinamide | 1262683-03-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: (S)-2-chlorotetrafluoroethanesulfinamide
• 英文别名: (S)-2-chloro-1,1,2,2-tetrafluoroethanesulfinamide
• CAS: 1262683-03-3
• 化学式: C₂H₂ClF₄NOS
• 分子量: 199.557
• InChiKey: WXHBBBGYCQEEAG-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-chlorotetrafluoroethanesulfinamide 、 1-萘甲醛 在 titanium(IV) isopropylate 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(S)-N-(1-naphthylmethylidene)-2-chlorotetrafluoroethanesulfinamide
  参考文献：
  名称：

  2-氯四氟乙烷亚磺酰胺诱导的不对称乙烯基曼尼希反应

  摘要：

  研究了（S）-2-氯四氟乙烷亚磺酰胺（CTFSA）引起的不对称乙烯基曼尼希（AVM）加成反应的一般性。从（衍生醛亚胺的反应小号）-CTFSA与2-（叔-butyldimethylsilyloxy）呋喃（TBSOF）发生在区域选择性空气气氛下，在DMSO室温下的γ部位，得到期望的加成产物中顺式构型与高非对映选择性（高达98：2 dr）。然而，在-78℃下在四丁基氟化铵（TBAF）存在下获得了作为主要异构体的抗构型产物。无需除去差向异构体即可轻松除去辅助基团，表明它们具有合成哌啶酮衍生物的潜力。

  DOI：

  10.1016/j.tet.2013.12.071
• 作为产物：
  描述：

  在 氯化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 (S)-2-chlorotetrafluoroethanesulfinamide
  参考文献：
  名称：

  多氟烷烃亚磺酰胺诱导的酮的一锅不对称还原胺化

  摘要：

  使用手性2-氯-1,1,2,2-四氟乙烷-1-亚磺酰胺作为辅助剂，在硼氢化钠存在下，实现了用于酮的不对称还原胺化的有效一锅法。芳族酮和脂族酮均反应良好，以良好的收率和优异的非对映选择性，得到相应的亚磺酰基酰胺。

  DOI：

  10.1016/j.jfluchem.2015.01.019

文献信息

• Per(poly)fluoroalkanesulfinamides assisted diastereoselective three-component inverse-electron-demand aza Diels–Alder reaction
  作者：Peng Li、Li-Juan Liu、Jin-Tao Liu

  DOI：10.1039/c0ob00699h

  日期：——

  A highly diastereoselective three-component inverse-electron-demand aza Diels–Alder reaction assisted by per(poly)fluoro-alkanesulfinamides is presented, providing a broad spectrum of highly functionalized piperidine derivatives with excellent endo/exo and facial diastereoselectivities. The electron-withdrawing perfluoroalkyl groups are crucial for the success of this reaction under mild conditions and facilitate monitoring the process and stereoselectivities of the reaction. The synthetic potential of these cycloadducts is also highlighted.

  报道了一种由全（多）氟烷基亚磺酰胺协助的高度立体选择性的三组分逆电子需求aza-Diels-Alder反应，提供了广泛的高度功能化的哌啶衍生物，具有优异的内型/外型和面立体选择性。吸电子的全氟烷基对于该反应在温和条件下的成功至关重要，并有助于监测反应过程和立体选择性。这些环加合物的合成潜力也得到了强调。
• Synthesis of Chiral β-Aminomalonates from 2-Chlorotetrafluoroethanesulfinyl Aldimines through the Mannich Reaction
  作者：Kai Yang、Min Jiang、Jin-Tao Liu

  DOI：10.1002/ejoc.201500134

  日期：2015.5

  An efficient method for the synthesis of chiral β-aminomalonates in good yields and with high diastereoselectivities was achieved through Mannich reactions between 2-chlorotetrafluoroethanesulfinyl aldimines and dialkyl malonates in the presence of N-trimethylsilylimidazole. Further transformation of the products gave the corresponding β-lactams in good yields and with high optical purities.

  在 N-三甲基甲硅烷基咪唑的存在下，通过 2-氯四氟乙亚磺酰基醛亚胺和丙二酸二烷基酯之间的曼尼希反应，实现了一种以高产率和高非对映选择性合成手性 β-氨基丙二酸酯的有效方法。产物的进一步转化以良好的产率和高光学纯度得到相应的β-内酰胺。
• The Synthesis and Strecker Reaction of 2-Chlorotetrafluoroethanesulfinyl Ketimines
  作者：Kai Yang、Li-Juan Liu、Jin-Tao Liu

  DOI：10.1021/jo500008e

  日期：2014.4.4

  A series of 2-chlorotetrafluoroethanesulfinyl ketimines were prepared from 2-chlorotetrafluoroethanesulfinamide and ketones in high yields, and their Strecker reactions with TMSCN have been investigated. High yields and excellent diastereoselectivities were achieved in the presence of a catalytic amount of CsF under mild conditions. The six-membered chairlike models were proposed to account for the high stereoselective Strecker reaction.
• Zinc promoted asymmetric propargylation of N -(2-chlorotetrafluoroethanesulfin)imines
  作者：Li-Juan Liu、Jin-Tao Liu

  DOI：10.1016/j.jfluchem.2014.08.008

  日期：2014.12

  Zinc promoted asymmetric Barbier-type homopropargylation of aldimines is demonstrated. 2-Chlorotetrafluoroethanesulfinamide was used as the chiral auxiliary and the corresponding homopropargylamines were obtained in good yields with up to 98% diastereoselectivity under mild conditions. (C) 2014 Elsevier B.V. All rights reserved.
• Optically Pure Polyfluoroalkanesulfinamides: Synthesis and Application as Promising and Monitorable Chiral Auxiliaries
  作者：Li-Juan Liu、Ling-Jun Chen、Peng Li、Xiao-Bo Li、Jin-Tao Liu

  DOI：10.1021/jo200119x

  日期：2011.6.3

  Efficient synthesis of enantiopure polyfluoroalkanesulfinamides (PFSAs) has been achieved. Their application as novel chiral auxiliaries with an electron-withdrawing and F-19 NMR monitorable polyfluoroalkyl group was initially demonstrated in an asymmetric Strecker reaction under mild conditions.