Toluene-4-sulfonic acid 4-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-butyl ester | 461417-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid 4-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-butyl ester
• CAS: 461417-85-6
• 化学式: C₂₀H₂₈O₃S
• 分子量: 348.507
• InChiKey: FYTZBRDCDSPZOM-HKUYNNGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid 4-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-butyl ester 在 sodium bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以66%的产率得到(1R,5S)-2-(4-Bromo-butyl)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene
  参考文献：
  名称：

  Synthesis of cardamom peroxide analogues by radical cyclization of hydroperoxyalkenes

  摘要：

  Three pinenic hydroperoxides were synthesized according to the Dussault method. Two of them could cyclize under radical conditions to give the exo-trig isomer as a single regioisomer. Only five- and six-member ring peroxides were obtained, whereas none of the possible seven-member ones was observed. This strategy could be employed in the total synthesis of cardamom peroxide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01122-x
• 作为产物：
  描述：

  beta-pinene 在 吡啶 、 sodium tetrahydroborate 、 zinc dibromide 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 101.0h， 生成 Toluene-4-sulfonic acid 4-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-butyl ester
  参考文献：
  名称：

  Synthesis of cardamom peroxide analogues by radical cyclization of hydroperoxyalkenes

  摘要：

  Three pinenic hydroperoxides were synthesized according to the Dussault method. Two of them could cyclize under radical conditions to give the exo-trig isomer as a single regioisomer. Only five- and six-member ring peroxides were obtained, whereas none of the possible seven-member ones was observed. This strategy could be employed in the total synthesis of cardamom peroxide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01122-x