cis-menthonetosylhydrazone | 144786-61-8

• 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: cis-menthonetosylhydrazone
• 英文别名: isomenthonetosylhydrazone；4-methyl-N-[(E)-[(2R,5R)-5-methyl-2-propan-2-ylcyclohexylidene]amino]benzenesulfonamide
• CAS: 144786-61-8
• 化学式: C₁₇H₂₆N₂O₂S
• 分子量: 322.472
• InChiKey: BXRWSQVTYFNXCJ-ANTVTUJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-menthonetosylhydrazone 在 palladium on activated charcoal lithium aluminium tetrahydride 、 正丁基锂 、 四甲基乙二胺 、 氢气 作用下， 以 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 3.84h， 生成 cis-8-hydroxycalamenene
  参考文献：
  名称：

  Aromatic annulation on the p-menthane monoterpenes: enantiospecific synthesis of the trans and cis isomers of calamenene and 8-hydroxycalamenene

  摘要：

  A new enantiospecific route to sesquiterpenes of the calamenene family is described. The synthetic pathway starts from easily available 3-oxygenated-p-menthane monoterpenes and affords the title compounds by a homologation-benzannulation sequence. The trans and cis isomers of the natural compounds calamenene and 8-hydroxycalamenene were obtained in enantiopure form starting from (-)-menthone and (+)-isomenthone, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.037
• 作为产物：
  描述：

  (-)-薄荷酮 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 cis-menthonetosylhydrazone
  参考文献：
  名称：

  Garner, Charles M.; Mossman, Brett C.; Prince, Mark E., Tetrahedron Letters, 1993, vol. 34, # 27, p. 4273 - 4276

  摘要：

  DOI：

文献信息

• Garner, Charles M.; Mossman, Brett C.; Prince, Mark E., Tetrahedron Letters, 1993, vol. 34, # 27, p. 4273 - 4276
  作者：Garner, Charles M.、Mossman, Brett C.、Prince, Mark E.

  DOI：——

  日期：——
• Aromatic annulation on the p-menthane monoterpenes: enantiospecific synthesis of the trans and cis isomers of calamenene and 8-hydroxycalamenene
  作者：Stefano Serra、Claudio Fuganti

  DOI：10.1016/j.tetlet.2005.05.037

  日期：2005.7

  A new enantiospecific route to sesquiterpenes of the calamenene family is described. The synthetic pathway starts from easily available 3-oxygenated-p-menthane monoterpenes and affords the title compounds by a homologation-benzannulation sequence. The trans and cis isomers of the natural compounds calamenene and 8-hydroxycalamenene were obtained in enantiopure form starting from (-)-menthone and (+)-isomenthone, respectively. (c) 2005 Elsevier Ltd. All rights reserved.