(E)-rac-(2'-buten-1',4'-olido)-[3',4':1,2]-6-fluoro-2-methyl-3-(4-methylthiobenzylidene)-indan

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (E)-rac-(2'-buten-1',4'-olido)-[3',4':1,2]-6-fluoro-2-methyl-3-(4-methylthiobenzylidene)-indan
• 英文别名: (E)-5-fluoro-8a-methyl-8-(4-(methylthio)benzylidene)-8,8a-dihydro-2H-indeno[2,1-b]furan-2-one；sulindac sulfide lactone；(4E)-7-fluoro-3a-methyl-4-[(4-methylsulfanylphenyl)methylidene]indeno[2,1-b]furan-2-one
• 化学式: C₂₀H₁₅FO₂S
• 分子量: 338.402
• InChiKey: QVFZAPNUKCBRTD-RQZCQDPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-rac-(2'-buten-1',4'-olido)-[3',4':1,2]-6-fluoro-2-methyl-3-(4-methylthiobenzylidene)-indan 在 sodium periodate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 40.0h， 以70%的产率得到(E)-5-fluoro-8a-methyl-8-(4-(methylsulfanyl)benzylidene)-8,8a-dihydro-2H-indeno[2,1-b]furan-2-one
  参考文献：
  名称：

  Accidental discovery of a ‘longer-range’ vinylogous Pummerer-type lactonization: formation of sulindac sulfide lactone from sulindac

  摘要：

  Unexpected formation of sulindac sulfide lactone occurred when sulindac was treated with oxalyl chloride and triethylamine. Structurally analogous sulindac sulfide and indomethacin did not undergo such lactonization under similar reaction conditions. We believe that the sulfoxide function in sulindac plays a pivotal role possibly via a 'longer-range' vinylogous Pummerer-type reaction as a driving force for the observed lactonization. The structure of the lactone was confirmed by single crystal X-ray analysis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.008
• 作为产物：
  描述：

  Sulindac 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以67%的产率得到(E)-rac-(2'-buten-1',4'-olido)-[3',4':1,2]-6-fluoro-2-methyl-3-(4-methylthiobenzylidene)-indan
  参考文献：
  名称：

  Accidental discovery of a ‘longer-range’ vinylogous Pummerer-type lactonization: formation of sulindac sulfide lactone from sulindac

  摘要：

  Unexpected formation of sulindac sulfide lactone occurred when sulindac was treated with oxalyl chloride and triethylamine. Structurally analogous sulindac sulfide and indomethacin did not undergo such lactonization under similar reaction conditions. We believe that the sulfoxide function in sulindac plays a pivotal role possibly via a 'longer-range' vinylogous Pummerer-type reaction as a driving force for the observed lactonization. The structure of the lactone was confirmed by single crystal X-ray analysis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.008

文献信息

• Sulfoxide Reduction/C(sp³)–S Metathesis Cascade in Ionic Liquid
  作者：Chenjing Liu、Dengfeng Chen、Yuanyuan Fu、Fei Wang、Jinyue Luo、Shenlin Huang

  DOI：10.1021/acs.orglett.0c02089

  日期：2020.7.17

  A sulfoxide reduction/C-S bond metathesis cascade between sulfoxides and alkyl bromides has been developed to access high-value sulfides without the use of any catalysts or bases. In this cascade, classical Kornblum oxidation is employed to reduce sulfoxides with alkyl bromides in ionic liquid. This protocol features high functional tolerance, mild conditions, promising scalability, and sustainable solvents.
• Synthesis of radioactive sulindac-sulfone-lactone via sulfonium salt and14C alkylhalide
  作者：Gerhard J. Sperl、Rifat Pamukcu、Klaus Brendel、Paul H. Gross

  DOI：10.1002/(sici)1099-1344(199909)42:9<877::aid-jlcr251>3.0.co;2-l

  日期：1999.9
• Accidental discovery of a ‘longer-range’ vinylogous Pummerer-type lactonization: formation of sulindac sulfide lactone from sulindac
  作者：Somnath Halder、Apparao Satyam

  DOI：10.1016/j.tetlet.2011.01.008

  日期：2011.3

  Unexpected formation of sulindac sulfide lactone occurred when sulindac was treated with oxalyl chloride and triethylamine. Structurally analogous sulindac sulfide and indomethacin did not undergo such lactonization under similar reaction conditions. We believe that the sulfoxide function in sulindac plays a pivotal role possibly via a 'longer-range' vinylogous Pummerer-type reaction as a driving force for the observed lactonization. The structure of the lactone was confirmed by single crystal X-ray analysis. (C) 2011 Elsevier Ltd. All rights reserved.