2-[(1-fluorovinyl)sulfonyl]-1,3-benzothiazole | 1200123-14-3

• 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: 2-[(1-fluorovinyl)sulfonyl]-1,3-benzothiazole
• 英文别名: 2-((1-Fluorovinyl)sulfonyl)benzo[d]thiazole；2-(1-fluoroethenylsulfonyl)-1,3-benzothiazole
• CAS: 1200123-14-3
• 化学式: C₉H₆FNO₂S₂
• 分子量: 243.283
• InChiKey: NKKNTMTZBNXVOG-UHFFFAOYSA-N

物化性质

• 熔点：
  141-142 °C
• 沸点：
  390.8±44.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(1-fluorovinyl)sulfonyl]-1,3-benzothiazole 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 64.0h， 生成 3-benzoyl-1-[2-(1,3-benzothiazole-2-sulfonyl)-2-fluoroethyl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
  参考文献：
  名称：

  Aza-Michael Access to Fluoroalkylidene Analogues of Biomolecules

  摘要：

  The synthesis of fluoroaminosulfones derived from piperidine and nucleic bases followed by the study of their chemical behavior in the modified Julia reaction are described. The resulting aminosulfones open a straightforward access to a series of new fluorinated biomolecules including a potent DPP-II inhibitor and acyclonucleoside analogues as potential enzyme inhibitors.

  DOI：

  10.1021/jo401356j
• 作为产物：
  描述：

  在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到2-[(1-fluorovinyl)sulfonyl]-1,3-benzothiazole
  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。
• Selective preparation of tetrasubstituted fluoroalkenes by fluorine-directed oxetane ring-opening reactions
  作者：Clément Q Fontenelle、Thibault Thierry、Romain Laporte、Emmanuel Pfund、Thierry Lequeux

  DOI：10.3762/bjoc.16.160

  日期：——

  The selective ring-opening reaction of fluoroalkylidene-oxetanes was directed by the presence of the fluorine atom, enabling a two-step access to tetrasubstituted fluoroalkenes with excellent geometry control. Despite its small van der Waals radii electronic, rather than steric influences of the fluorine atom governed the ring-opening reaction with bromide ions, even in the presence of bulky substituents

  氟代亚烷基-氧杂环丁烷的选择性开环反应是通过氟原子的存在来进行的，从而使两步接触四取代的氟代烯烃具有极好的几何形状控制。尽管其范德华半径电子较小，即使存在大的取代基，氟原子的空间影响也并非由空间影响，而是由溴离子控制。
• [EN] MACROCYCLIC SPIROCYCLE DERIVATIVES AS MCL-1 INHIBITORS<br/>[FR] DÉRIVÉS DE SPIROCYCLES MACROCYCLIQUES EN TANT QU'INHIBITEURS DE MCL-1
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2021005043A1

  公开（公告）日：2021-01-14

  The present invention relates to pharmaceutical agents of formula (I) useful for therapy and/or prophylaxis in a subject, pharmaceutical composition comprising such compounds, and their use as MCL-1 inhibitors, useful for treating diseases such as cancer.

  本发明涉及一种公式（I）的药物制剂，用于治疗和/或预防受试者的药物组合物包括这种化合物，并且它们作为MCL-1抑制剂的用途，用于治疗癌症等疾病。
• 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。
• Fluorinated hydroxypiperidines as selective β-glucosidase inhibitors
  作者：Clothilde Le Guen、Teresa Mena-Barragán、Carmen Ortiz Mellet、David Gueyrard、Emmanuel Pfund、Thierry Lequeux

  DOI：10.1039/c5ob00721f

  日期：——

  Synthesis and glucosidase inhibitory activity of piperidines revealed a reverse selectivity between F- and H-alkenes.

  合成了吡啶类化合物，并测定了它们对葡萄糖苷酶的抑制活性，结果发现F-和H-烯烃之间存在反向选择性。