toluene-4-sulfonic acid 4,4-di-p-tolyl-but-3-en-1-yl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: toluene-4-sulfonic acid 4,4-di-p-tolyl-but-3-en-1-yl ester
• 英文别名: 4,4-bis(4-methylphenyl)but-3-enyl 4-methylbenzenesulfonate
• 化学式: C₂₅H₂₆O₃S
• 分子量: 406.546
• InChiKey: WAKWKAXMPDXQJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲苯磺酸 、 [bis(p-tolyl)methylene]cyclopropane 以 1,2-二氯乙烷 为溶剂， 反应 0.08h， 以77%的产率得到toluene-4-sulfonic acid 4,4-di-p-tolyl-but-3-en-1-yl ester
  参考文献：
  名称：

  Brønsted acid-mediated ring-opening reactions of methylenecyclopropanes: a dramatic counter ion effect

  摘要：

  We report herein two different ring-opening patterns of methylenecyclopropanes (MCPs) in the presence of two Bronsted acids heptadecafluorooctane-1-sulfonic acid (C8F17SO3H) and toluene p-sulfonic acid (TsOH) under mild conditions: (a) the ring-opening of MCPs by H2O and subsequent etherification give the corresponding homoallylic ethers in the presence of heptadecafluorooctane-1-sulfonic acid; (b) the direct ring-opening of MCPs by the Bronsted acid gives the corresponding homoallylic alcohol derivatives in the presence of toluene p-sulfonic acid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.105

文献信息

• Brønsted acid-mediated ring-opening reactions of methylenecyclopropanes: a dramatic counter ion effect
  作者：Li-Xiong Shao、Jin-Wen Huang、Min Shi

  DOI：10.1016/j.tet.2004.09.105

  日期：2004.12

  We report herein two different ring-opening patterns of methylenecyclopropanes (MCPs) in the presence of two Bronsted acids heptadecafluorooctane-1-sulfonic acid (C8F17SO3H) and toluene p-sulfonic acid (TsOH) under mild conditions: (a) the ring-opening of MCPs by H2O and subsequent etherification give the corresponding homoallylic ethers in the presence of heptadecafluorooctane-1-sulfonic acid; (b) the direct ring-opening of MCPs by the Bronsted acid gives the corresponding homoallylic alcohol derivatives in the presence of toluene p-sulfonic acid. (C) 2004 Elsevier Ltd. All rights reserved.