4-bromo-5-(ethylthio)furan-2(5H)-one | 148777-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4-bromo-5-(ethylthio)furan-2(5H)-one
• 英文别名: 4-bromo-5-ethylthio-2(5H)-furanone；4-bromo-5-ethylthiofuran-2(5H)-one；3-bromo-2-ethylsulfanyl-2H-furan-5-one
• CAS: 148777-29-1
• 化学式: C₆H₇BrO₂S
• 分子量: 223.09
• InChiKey: HSTBVDZYDIFVAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-5-(ethylthio)furan-2(5H)-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以70%的产率得到4-bromo-5-ethylsulfonylfuran-2(5H)-one
  参考文献：
  名称：

  Pseudoesters and Derivatives. XXXI¹. Synthesis of 5-Ethylthio-, 5-Ethylsulfinyl- and 5-Ethylsulfonylfuran-2(5H)-ones

  摘要：

  Convenient syntheses of 5-(ethylthio)furan-2(5H)-ones 2a-k from the appropriate 5-methoxyfuran-2(5H)-one 1a-g are described. The oxidation to the corresponding sulfoxides 5a-c and sulfones 6a-f is also reported.

  DOI：

  10.1080/00397919308009801
• 作为产物：
  描述：

  5-(ethylthio)furan-2(5H)-one 在 溴 作用下， 以 苯 为溶剂， 生成 4-bromo-5-(ethylthio)furan-2(5H)-one
  参考文献：
  名称：

  Pseudoesters and Derivatives. XXXI¹. Synthesis of 5-Ethylthio-, 5-Ethylsulfinyl- and 5-Ethylsulfonylfuran-2(5H)-ones

  摘要：

  Convenient syntheses of 5-(ethylthio)furan-2(5H)-ones 2a-k from the appropriate 5-methoxyfuran-2(5H)-one 1a-g are described. The oxidation to the corresponding sulfoxides 5a-c and sulfones 6a-f is also reported.

  DOI：

  10.1080/00397919308009801

文献信息

• Polycyclic Hydroxyquinones. Part 29. Regioselective Reactions of 5-sulphur-substituted furan-2(5H)-one anions with naphthoquinone monoketals. Application to the synthesis of anthracyclinone precursors
  作者：Pablo Asenjo、Francisco Fariña、M.Victoria Martín、M.Carmen Paredes、J.Javier Soto

  DOI：10.1016/s0040-4020(96)01100-3

  日期：1997.2

  afford exclusively the C-5 substituted Michael adducts in good yield. The annelation reactions of the anions generated from furanones 30 and 33 with naphthoquinone monoketals 11 and 12 lead to 2-sulphur-substituted 1,4-anthraquinones 32, 35 and 36. Diels-Alder reaction of the 1,4-anthraquinones 41 and 42 with (E)-1,3-bis[(trimethylsilyl)oxy]buta-1,3-diene (37) affords ABCD tetracyclic systems related

  呋喃酮7 – 10的阴离子与萘醌单缩酮11 – 15反应，以高收率完全提供C-5取代的Michael加合物。从呋喃酮产生的阴离子的成环反应30和33与萘醌单缩酮11和12引到2-硫取代的1,4-亚蒽醌32，35和36。1,4-蒽醌41和42与（E）-1,3-双[（三甲基甲硅烷基）氧基] buta-1,3-二烯的Diels-Alder反应（37）提供了与蒽环素存在的那些相关的ABCD四环系统。
• Pseudoesters and Derivatives XXXV. Reactions of 4-Substituted-5-(Ethylthio)Furan-2(5H)-Ones Anions with Alkylating Agents
  作者：Francisco Fariña、M. Victoria Martín、Ana Martínez de Guereñu

  DOI：10.1080/00397919608004570

  日期：1996.7

  Abstract Alkylation of anions derived from 5-ethylthio-4-substituted furanones (1–3) is described. The regioselectivity depends on the alkylating agent but mainly on the nature of the substituent. The alkylation of 4-methoxyfuranone 3 proceeds regioselectively to afford the 5-alkylated derivative as sole product.

  摘要 描述了衍生自 5-乙硫基-4-取代呋喃酮 (1-3) 的阴离子的烷基化。区域选择性取决于烷化剂，但主要取决于取代基的性质。4-甲氧基呋喃酮 3 的烷基化区域选择性地进行以提供作为唯一产物的 5-烷基化衍生物。
• Synthesis of 2-sulphur-substituted 1,4-anthraquinones. Application to the Synthesis of Anthracyclinone Precursors
  作者：P Asenjo

  DOI：10.1016/00404-0399(50)17395-

  日期：1995.11.6

  2-sulphur-substituted 1,4-anthraquinones 8a,b and 10 have been prepared by annelation reactions of the anions of furanones 5a,b with naphthoquinone monoketals of type 6 and 9. Diels-Alder reaction of the 1,4-anthraquinones 11a,b with (E)-1,3-bis(trimethylsilyloxy)buta-1,3-diene (12) affords ABCD tetracyclic systems related to those existing in anthracyclinones.