2-(benzo[b]thiophen-2-yl)but-3-en-2-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-(benzo[b]thiophen-2-yl)but-3-en-2-ol
• 英文别名: 2-(1-Benzothiophen-2-yl)but-3-en-2-ol；2-(1-benzothiophen-2-yl)but-3-en-2-ol
• 化学式: C₁₂H₁₂OS
• 分子量: 204.293
• InChiKey: ZQSUNBDRQXABNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴氟甲基膦酸二乙酯 、 2-(benzo[b]thiophen-2-yl)but-3-en-2-ol 在 咪唑 、 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以84%的产率得到diethyl (3-(benzo[b]thiophen-2-yl)-1,1-difluoro-4-oxopentyl)phosphonate
  参考文献：
  名称：

  Visible-Light Photocatalytic Difluoroalkylation-Induced 1, 2-Heteroarene Migration of Allylic Alcohols in Batch and Flow

  摘要：

  A convenient method for the preparation of sp(3)-rich heterocycles is reported. The method comprises a photocatalytic difluoroalkylation-induced 1,2-heteroarene migration of allylic alcohols. Here we describe for the first time the benefits of using flow to facilitate such migration reactions, including shorter reaction times, higher selectivities, and opportunities to scale the chemistry.

  DOI：

  10.1021/acs.joc.8b01624
• 作为产物：
  描述：

  2-乙酰基苯并噻吩 、 乙烯基溴化镁 以 四氢呋喃 为溶剂， 反应 0.08h， 以85%的产率得到2-(benzo[b]thiophen-2-yl)but-3-en-2-ol
  参考文献：
  名称：

  Visible-Light Photocatalytic Difluoroalkylation-Induced 1, 2-Heteroarene Migration of Allylic Alcohols in Batch and Flow

  摘要：

  A convenient method for the preparation of sp(3)-rich heterocycles is reported. The method comprises a photocatalytic difluoroalkylation-induced 1,2-heteroarene migration of allylic alcohols. Here we describe for the first time the benefits of using flow to facilitate such migration reactions, including shorter reaction times, higher selectivities, and opportunities to scale the chemistry.

  DOI：

  10.1021/acs.joc.8b01624

文献信息

• Visible-Light Photocatalytic Difluoroalkylation-Induced 1, 2-Heteroarene Migration of Allylic Alcohols in Batch and Flow
  作者：Xiao-Jing Wei、Timothy Noël

  DOI：10.1021/acs.joc.8b01624

  日期：2018.9.21

  A convenient method for the preparation of sp(3)-rich heterocycles is reported. The method comprises a photocatalytic difluoroalkylation-induced 1,2-heteroarene migration of allylic alcohols. Here we describe for the first time the benefits of using flow to facilitate such migration reactions, including shorter reaction times, higher selectivities, and opportunities to scale the chemistry.