3-[4-(Methanesulfonyloxy)benzoyl]-2-[4-(methanesulfonyloxy)phenyl]-1-benzothiophen-6-yl methanesulfonate | 1390631-69-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[4-(Methanesulfonyloxy)benzoyl]-2-[4-(methanesulfonyloxy)phenyl]-1-benzothiophen-6-yl methanesulfonate
• 英文别名: [4-[6-methylsulfonyloxy-3-(4-methylsulfonyloxybenzoyl)-1-benzothiophen-2-yl]phenyl] methanesulfonate
• CAS: 1390631-69-2
• 化学式: C₂₄H₂₀O₁₀S₄
• 分子量: 596.681
• InChiKey: HYMVJNSJTDLXPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  147.18
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3-[4-(Methanesulfonyloxy)benzoyl]-2-[4-(methanesulfonyloxy)phenyl]-1-benzothiophen-6-yl methanesulfonate 在 potassium hydroxide 、 sodium t-butanolate 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 16.0h， 生成 雷洛昔芬
  参考文献：
  名称：

  Synthesis of Aryl Ethers via a Sulfonyl Transfer Reaction

  摘要：

  A general synthesis of aryl ethers from primary and secondary alcohols and aryl mesylates is presented. The reaction proceeds via a sulfonyl-transfer mechanism. In this paper, we compare the sulfonyl transfer reaction to Mitsunobu ether formation. The reaction can be employed in a multistep synthesis where the aryl mesylate is used as a phenol protecting group and then as an activating group for ether formation. This protecting/activating group strategy is demonstrated using raloxifene as the target.

  DOI：

  10.1021/ol301615z
• 作为产物：
  描述：

  2-[4-[(甲磺酰)氧]苯基]-苯并[b]噻吩-6-醇 6-甲烷磺酸 、 4-Mesyloxy-benzoylchlorid 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 20.5h， 以62%的产率得到3-[4-(Methanesulfonyloxy)benzoyl]-2-[4-(methanesulfonyloxy)phenyl]-1-benzothiophen-6-yl methanesulfonate
  参考文献：
  名称：

  Synthesis of Aryl Ethers via a Sulfonyl Transfer Reaction

  摘要：

  A general synthesis of aryl ethers from primary and secondary alcohols and aryl mesylates is presented. The reaction proceeds via a sulfonyl-transfer mechanism. In this paper, we compare the sulfonyl transfer reaction to Mitsunobu ether formation. The reaction can be employed in a multistep synthesis where the aryl mesylate is used as a phenol protecting group and then as an activating group for ether formation. This protecting/activating group strategy is demonstrated using raloxifene as the target.

  DOI：

  10.1021/ol301615z

文献信息

• Org. Lett. 2012, 14, 3886-3889
  作者：

  DOI：——

  日期：——