(4R,5R,9S,10R,11S)-morel-2-en-7-one | 667917-32-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R,9S,10R,11S)-morel-2-en-7-one
• 英文别名: (1S,2R,3S,7R,8R)-2,6,6,9-tetramethyltricyclo[5.4.0.03,8]undec-9-en-5-one
• CAS: 667917-32-0
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: KTZOECZKAGADFF-CAFXUDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4R,5R,9S,10R,11S)-morel-2-en-7-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以49%的产率得到(4R,5R,7R,9S,10R,11S)-morel-2-en-7-ol
  参考文献：
  名称：

  Preparation of Moreliane-Derived Volatile Sesquiterpenes

  摘要：

  A series of six volatile sesquiterpenes (9-13 and 15) was prepared by thioketalization of (4R,5S,9S,10S,11S)morel-2-en-1,7-dione (2) and of (4R,5S,7R,9R,11R)-moreli-2,10-dien-7-ol-1-one (3), followed by Raneynickel desulfurization. The structures of the new substances were determined by 1D and 2D NMR including COSY, NOESY, HSQC, and HMBC experiments. The geometry of (3S,4R,5R,9S,10R,11S)morelian-7-one (11), which exhibited an intense woody odor, was calculated by density functional theory at the B3LYP/6-31G* level.

  DOI：

  10.1021/np030354e
• 作为产物：
  描述：

  (1S,4aR,5S,7R,8aS,9S)-7-Hydroxy-4,8,8,9-tetramethyl-4a,5,6,7,8,8a-hexahydro-1H-1,5-methano-naphthalen-2-one 在 W-2 Raney-nickel 、 对甲苯磺酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 3.0h， 生成 (4R,5R,9S,10R,11S)-morel-2-en-7-one
  参考文献：
  名称：

  Preparation of Moreliane-Derived Volatile Sesquiterpenes

  摘要：

  A series of six volatile sesquiterpenes (9-13 and 15) was prepared by thioketalization of (4R,5S,9S,10S,11S)morel-2-en-1,7-dione (2) and of (4R,5S,7R,9R,11R)-moreli-2,10-dien-7-ol-1-one (3), followed by Raneynickel desulfurization. The structures of the new substances were determined by 1D and 2D NMR including COSY, NOESY, HSQC, and HMBC experiments. The geometry of (3S,4R,5R,9S,10R,11S)morelian-7-one (11), which exhibited an intense woody odor, was calculated by density functional theory at the B3LYP/6-31G* level.

  DOI：

  10.1021/np030354e

文献信息

• Preparation of Moreliane-Derived Volatile Sesquiterpenes
  作者：Carlos M. Cerda-García-Rojas、María A. Bucio、Luisa U. Román、Juan D. Hernández、Pedro Joseph-Nathan

  DOI：10.1021/np030354e

  日期：2004.2.1

  A series of six volatile sesquiterpenes (9-13 and 15) was prepared by thioketalization of (4R,5S,9S,10S,11S)morel-2-en-1,7-dione (2) and of (4R,5S,7R,9R,11R)-moreli-2,10-dien-7-ol-1-one (3), followed by Raneynickel desulfurization. The structures of the new substances were determined by 1D and 2D NMR including COSY, NOESY, HSQC, and HMBC experiments. The geometry of (3S,4R,5R,9S,10R,11S)morelian-7-one (11), which exhibited an intense woody odor, was calculated by density functional theory at the B3LYP/6-31G* level.