3,3,6,7,8-pentamethyl-1-methylthio-3,4-dihydroisoquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: 3,3,6,7,8-pentamethyl-1-methylthio-3,4-dihydroisoquinoline
• 英文别名: 3,3,6,7,8-pentamethyl-1-methylsulfanyl-4H-isoquinoline
• 化学式: C₁₅H₂₁NS
• 分子量: 247.404
• InChiKey: NYHYLIRSUDAATJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  硫氰酸甲酯 、 三甲苯 、 异丁醛 在 硫酸 、 水 作用下， 以52%的产率得到3,3,5,6,7-pentamethyl-1-methylthio-3,4-dihydroisoquinoline
  参考文献：
  名称：

  Regioisomerism in the Ritter reaction. 1. Synthesis of 3,3,5,6,7-, 3,3,6,7,8-, 3,3,5,7,8-, and 3,3,5,6,8-pentamethyl-3,4-dihydroisoquinolines from 1,2,3- and 1,2,4-trimethylbenzenes

  摘要：

  Reactions of 1,2,3- or 1,2,4-trimethylbenzene with isobutyraldehyde and ethyl cyanoacetate (ECA) or reactions of the corresponding 1-aryl-2-methylpropan-1-ols with ECA afforded isomeric 3,3,5,6,7-, 3,3,6,7,8-, 3,3,5,7,8-, and 3,3,5,6,8-pentamethyl-3,4-dihydroisoquinotines. Isomerization is explained as the ring opening of a spiran intermediate in two possible ways followed by the Jacobsen rearrangement.

  DOI：

  10.1023/b:rucb.0000037862.92972.b4

文献信息

• Regioisomerism in the Ritter reaction. 1. Synthesis of 3,3,5,6,7-, 3,3,6,7,8-, 3,3,5,7,8-, and 3,3,5,6,8-pentamethyl-3,4-dihydroisoquinolines from 1,2,3- and 1,2,4-trimethylbenzenes
  作者：Yu. V. Shklyaev、R. R. Ismagilov、Yu. S. Rozhkova、A. A. Fatykhov、I. B. Abdrakhmanov、A. G. Tolstikov

  DOI：10.1023/b:rucb.0000037862.92972.b4

  日期：2004.4

  Reactions of 1,2,3- or 1,2,4-trimethylbenzene with isobutyraldehyde and ethyl cyanoacetate (ECA) or reactions of the corresponding 1-aryl-2-methylpropan-1-ols with ECA afforded isomeric 3,3,5,6,7-, 3,3,6,7,8-, 3,3,5,7,8-, and 3,3,5,6,8-pentamethyl-3,4-dihydroisoquinotines. Isomerization is explained as the ring opening of a spiran intermediate in two possible ways followed by the Jacobsen rearrangement.