(3R,4aS,9aR)-7-[(4-chlorobenzyl)thio]-1,2,3,4,4a,9,9a,10-octahydro-3,9,9-trimethyl-acridine | 1182348-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (3R,4aS,9aR)-7-[(4-chlorobenzyl)thio]-1,2,3,4,4a,9,9a,10-octahydro-3,9,9-trimethyl-acridine
• 英文别名: (3R,4aS,9aR)-7-[(4-chlorophenyl)methylsulfanyl]-3,9,9-trimethyl-2,3,4,4a,9a,10-hexahydro-1H-acridine
• CAS: 1182348-30-6
• 化学式: C₂₃H₂₈ClNS
• 分子量: 386.001
• InChiKey: ZCWOWZPWHPCRIN-MPHOGZCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (+)-香茅醛 、 4-(4-chloro-benzylsulfanyl)-phenylamine 在 silica-supported ZnCl2 (30%) 作用下， 反应 5.0h， 生成 (3R,4aS,9aS)-7-[(4-chlorobenzyl)thio]-1,2,3,4,4a,9,9a,10-octahydro-3,9,9-trimethyl-acridine 、 (3R,4aS,9aR)-7-[(4-chlorobenzyl)thio]-1,2,3,4,4a,9,9a,10-octahydro-3,9,9-trimethyl-acridine
  参考文献：
  名称：

  Atom-Economic Synthesis of Functionalized Octahydroacridines from Citronellal or 3-(Phenylthio)-citronellal

  摘要：

  Here we present a simple, solvent-free, one-pot, hetero-Diels-Alder reaction of (R)-citronellal or 3-(phenylthio)-citronellal with arylamines using solid-supported catalyst (SiO2/ZnCl2). This general, efficient, and improved method is selective, affording preferentially new trans-fused 3-(phenylthio)-octahydroacridines (S-OHAs) in good yields. The use of microwave irradiation facilitates the procedure and accelerates the reaction.

  DOI：

  10.1080/00397910802663469

文献信息

• Atom-Economic Synthesis of Functionalized Octahydroacridines from Citronellal or 3-(Phenylthio)-citronellal
  作者：Raquel G. Jacob、Márcio S. Silva、Samuel R. Mendes、Elton L. Borges、Eder J. Lenardão、Gelson Perin

  DOI：10.1080/00397910802663469

  日期：2009.7.7

  Here we present a simple, solvent-free, one-pot, hetero-Diels-Alder reaction of (R)-citronellal or 3-(phenylthio)-citronellal with arylamines using solid-supported catalyst (SiO2/ZnCl2). This general, efficient, and improved method is selective, affording preferentially new trans-fused 3-(phenylthio)-octahydroacridines (S-OHAs) in good yields. The use of microwave irradiation facilitates the procedure and accelerates the reaction.