diethyl ((benzothiazol-2-ylsulfonyl)fluoromethyl)phosphonate | 1200123-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: diethyl ((benzothiazol-2-ylsulfonyl)fluoromethyl)phosphonate
• 英文别名: 2-[Diethoxyphosphoryl(fluoro)methyl]sulfonyl-1,3-benzothiazole；2-[diethoxyphosphoryl(fluoro)methyl]sulfonyl-1,3-benzothiazole
• CAS: 1200123-15-4
• 化学式: C₁₂H₁₅FNO₅PS₂
• 分子量: 367.359
• InChiKey: XZRAGMXUDGUMJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl ((benzothiazol-2-ylsulfonyl)fluoromethyl)phosphonate 在 四丁基氟化铵 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 生成 2-{fluoro[3-(pyrrolidin-1-yl)oxetan-3-yl]methylsulfonyl}benzo[d]thiazole
  参考文献：
  名称：

  含氟 3,3-二取代氧杂环丁烷和亚烷基氧杂环丁烷的合成

  摘要：

  通过 Julia-Kocienski 反应从 3-氧杂环丁酮、3-氮杂环丁酮和氟砜实现了对氟亚烷基-氧杂环丁烷和 -氮杂环丁烷的访问。这种方法允许制备包含核碱基、酯或芳基砜功能和吡咯烷环的氟化四元环的新前体。苯并噻唑基砜介导的氮亲核试剂的氮杂-迈克尔加成反应能够获得 3,3-二取代氧杂环丁烷。

  DOI：

  10.1002/ejoc.201500172
• 作为产物：
  描述：

  2-((fluoromethyl)sulfonyl)benzo[d]thiazole 、 氯磷酸二乙酯 在 sodium hexamethyldisilazane 作用下， 反应 0.08h， 以75%的产率得到diethyl ((benzothiazol-2-ylsulfonyl)fluoromethyl)phosphonate
  参考文献：
  名称：

  Toward the Synthesis of Benzothiazolyl Fluoroaminosulfones

  摘要：

  Due to the importance of allylamines in organic synthesis, the synthesis of reagents as potent precursors of aminofluoroolefins is reported from functionalized benzothiazolylsulfones. The key intermediate, a fluorovinyl sulfone, was prepared and functionalized by addition of aliphatic, aromatic amines and amino acid alkyl esters through an aza-Michael addition reaction.

  DOI：

  10.1021/jo901540c

文献信息

• Photoinduced Nonstabilized Azomethine Ylide Formation for the Preparation of Fluorine Containing Pyrrolidines
  作者：Thibault Thierry、Cyril Lebargy、Emmanuel Pfund、Thierry Lequeux

  DOI：10.1021/acs.joc.9b00244

  日期：2019.5.3

  A mild and reproducible method for the formation of a nonstabilized azomethine ylide was developed by photoinduced reaction catalyzed with eosin Y under green light irradiation. Resulting 1,3-dipole was trapped with fluoroalkenes, fluoroalkylated alkenes, and representative dipolarophiles to access pyrrolidine scaffolds, including spirocyclic compounds. The mechanism involved in this transformation

  通过曙红Y在绿光照射下的光诱导反应，开发了一种温和且可重现的形成不稳定的偶氮甲碱叶立德的方法。所得的1,3-偶极子被氟代烯烃，氟代烷基化的烯烃和代表性的偶极亲和剂捕获，以进入吡咯烷骨架，包括螺环化合物。研究了参与该转化的机制，清楚地显示了曙红Y的催化氧化还原循环。
• Convergent access to mono-fluoroalkene-based peptidomimetics
  作者：Florent Larnaud、Charlène Calata、Anaïs Prunier、Clothilde Le Guen、Rémi Legay、Emmanuel Pfund、Thierry Lequeux

  DOI：10.1039/d1ob02441h

  日期：——

  The convergent and selective preparation of (Z)-monofluoroalkene-based dipeptide isosteres from functionalized fluorosulfones as a cornerstone is described. In this approach, the N-terminal amino group is introduced by a conjugate addition reaction of phthalimide onto fluorinated vinylsulfones containing α-amino-acid side chains while the C-terminal motif is linked to the fluorovinylic peptide bond

  描述了以功能化氟砜为基石聚合和选择性制备（ Z ）-单氟烯烃基二肽电子等排体。在这种方法中， N端氨基通过邻苯二甲酰亚胺的共轭加成反应引入到含有 α-氨基酸侧链的氟化乙烯砜上，而C端基序通过Julia-Kocienski 反应与氟乙烯基肽键模拟物连接介于氟砜和带有 α-氨基酸侧链的取代醛之间。
• Access to Fluoropyrrolidines by Intramolecular Aza-Michael Addition Reaction
  作者：Clothilde Le Guen、Minh-Loan Tran Do、Aurélien Chardon、Cyril Lebargy、Jean-François Lohier、Emmanuel Pfund、Thierry Lequeux

  DOI：10.1021/acs.joc.6b01363

  日期：2016.8.5

  Study of the intramolecular aza-Michael addition reaction from an aminofluorovinylsulfone opens a new route for the synthesis of pyrrolidine derivatives. An unexpected diastereoselective cyclization reaction was observed, leading preferentially to the anti-N-benzylpyrrolidine sulfone. The resulting sulfone was reacted with aldehydes to access β-substituted α-fluoroalkenyl pyrrolidines in one step.

  对氨基氟乙烯基砜进行分子内氮杂-迈克尔加成反应的研究为吡咯烷衍生物的合成开辟了一条新途径。一个意想不到的非对映选择性环化反应中观察到，优选地导致抗- Ñ -benzylpyrrolidine砜。一步将生成的砜与醛反应以生成β-取代的α-氟烯基吡咯烷。
• Synthesis of Fluorine-Containing 3,3-Disubstituted Oxetanes and Alkylidene Oxetanes
  作者：Romain Laporte、Anais Prunier、Emmanuel Pfund、Vincent Roy、Luigi A. Agrofoglio、Thierry Lequeux

  DOI：10.1002/ejoc.201500172

  日期：2015.5

  contain a nucleic base, an ester or aryl sulfone function, and a pyrrolidine ring. Benzothiazolyl-sulfone-mediated aza-Michael addition reaction of nitrogen nucleophiles enables access to 3,3-disubstituted oxetanes.

  通过 Julia-Kocienski 反应从 3-氧杂环丁酮、3-氮杂环丁酮和氟砜实现了对氟亚烷基-氧杂环丁烷和 -氮杂环丁烷的访问。这种方法允许制备包含核碱基、酯或芳基砜功能和吡咯烷环的氟化四元环的新前体。苯并噻唑基砜介导的氮亲核试剂的氮杂-迈克尔加成反应能够获得 3,3-二取代氧杂环丁烷。
• Toward the Synthesis of Benzothiazolyl Fluoroaminosulfones
  作者：Charlène Calata、Emmanuel Pfund、Thierry Lequeux

  DOI：10.1021/jo901540c

  日期：2009.12.18

  Due to the importance of allylamines in organic synthesis, the synthesis of reagents as potent precursors of aminofluoroolefins is reported from functionalized benzothiazolylsulfones. The key intermediate, a fluorovinyl sulfone, was prepared and functionalized by addition of aliphatic, aromatic amines and amino acid alkyl esters through an aza-Michael addition reaction.