2-(1-cyclobutenyl)thiophene | 291778-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(1-cyclobutenyl)thiophene
• 英文别名: 2-(cyclobuten-1-yl)thiophene
• CAS: 291778-16-0
• 化学式: C₈H₈S
• 分子量: 136.218
• InChiKey: UCGPGDIBJCPNIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  辛烯 、 2-(1-cyclobutenyl)thiophene 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以54%的产率得到2-[(E/Z)-1-methylene-4-undecenyl]thiophene
  参考文献：
  名称：

  High Regioselectivity in the Ring-Opening Cross-Metathesis of 1-Arylcyclobutene

  摘要：

  DOI：

  10.1002/1099-0690(200209)2002:17<2942::aid-ejoc2942>3.0.co;2-d
• 作为产物：
  描述：

  2-碘噻吩 、 1-bromobicyclo[1.1.0]butane 在 四(三苯基膦)钯 叔丁基锂 、 三丁基氯化锡 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 以88%的产率得到2-(1-cyclobutenyl)thiophene
  参考文献：
  名称：

  An Efficient Synthesis of Arylcyclobutenes via Cross-Coupling of Aryl Halides with 1-(Tri- n -butylstannyl)cyclobutene

  摘要：

  1-Tri-n-butylstannylcyclobutene, obtained from 1-bromocyclobutene by lithium/bromine exchange and transmetalation with chloro-tri-n-butylstannane, could be effectively converted with aryl halides into 1-arylcyclobutenes by the Stille cross-coupling procedure. Hetero-aryl halides like 2-bromopyridine and 2-iodothiophene were also successfully coupled, and in 1,3,5-tribromobenzene, 1,2,4,5-tetrabromobenzene and hexabromobenzene all bromine atoms could be exchanged. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00350-1

文献信息

• An Efficient Synthesis of Arylcyclobutenes via Cross-Coupling of Aryl Halides with 1-(Tri- n -butylstannyl)cyclobutene
  作者：Jing Feng、Günter Szeimies

  DOI：10.1016/s0040-4020(00)00350-1

  日期：2000.6

  1-Tri-n-butylstannylcyclobutene, obtained from 1-bromocyclobutene by lithium/bromine exchange and transmetalation with chloro-tri-n-butylstannane, could be effectively converted with aryl halides into 1-arylcyclobutenes by the Stille cross-coupling procedure. Hetero-aryl halides like 2-bromopyridine and 2-iodothiophene were also successfully coupled, and in 1,3,5-tribromobenzene, 1,2,4,5-tetrabromobenzene and hexabromobenzene all bromine atoms could be exchanged. (C) 2000 Elsevier Science Ltd. All rights reserved.
• High Regioselectivity in the Ring-Opening Cross-Metathesis of 1-Arylcyclobutene
  作者：Jing Feng、Günter Szeimies

  DOI：10.1002/1099-0690(200209)2002:17<2942::aid-ejoc2942>3.0.co;2-d

  日期：2002.9