(3R,4R,5R)-cis-clausenamidone | 608122-65-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R,5R)-cis-clausenamidone
• 英文别名: (3R,4R,5R)-3-hydroxy-1-methyl-4-phenyl-5-benzoylpyrrolidin-2-one；(3R,4R,5R)-5-benzoyl-3-hydroxy-1-methyl-4-phenylpyrrolidin-2-one
• CAS: 608122-65-2
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: XBQHNXLCOAIENZ-BFYDXBDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-cis-clausenamidone 在 sodium tetrahydroborate 、 水 、 sodium chloride 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.08h， 以98%的产率得到(-)-cis-clausenamide
  参考文献：
  名称：

  Lewis碱催化硝基烯烃活化的简明不对称合成完全取代的异恶唑啉-N-氧化物

  摘要：

  异恶唑啉N氧化物的转化：据报道，通过仲胺Lewis碱催化的硝基烯烃活化以及与醛和酰基化物的分子间缩合，简明地合成了异恶唑啉N氧化物。樟脑衍生的手性硫基化物的应用可得到对映异构体富集的异恶唑啉N-氧化物，具有出色的收率和立体选择性。异恶唑啉-N-氧化物的简单转化导致在四个步骤中以克级合成（-）-clausenamide类似物，并具有出色的立体化学控制（请参见方案）。

  DOI：

  10.1002/chem.201001237
• 作为产物：
  描述：

  (5R)-3,4-dehydroclausenamidone 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到(3R,4R,5R)-cis-clausenamidone
  参考文献：
  名称：

  Synthesis and activity in enhancing long-term potentiation (LTP) of clausenamide stereoisomers

  摘要：

  Clausenamide, isolated from aqueous extract of dry leaves of Clausena lansium, a Chinese folk medicine, was found to have potent activity in enhancing LTP and show nootropic activity in animal tests. In order to discovery more potent stereoisomers and to analyze the relationship of structure-activity, the synthesis of 16 (8 pairs) optically pure stereoisomers of clausenamide with four chiral centers was achieved. The results of LTP assay showed that the nootropic activity of the stereoisomers of clausenamide is closely related to the configuration of stereoisomers. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.018

文献信息

• Concise Asymmetric Synthesis of Fully Substituted Isoxazoline-N-Oxide through Lewis Base Catalyzed Nitroalkene Activation
  作者：Cheng Zhong、Lekh Nath S. Gautam、Jeffrey L. Petersen、Novruz G. Akhmedov、Xiaodong Shi

  DOI：10.1002/chem.201001237

  日期：2010.8.2

  Transforming isoxazoline‐N‐oxides: A concise asymmetric synthesis of isoxazoline‐N‐oxides is reported through secondary amine Lewis base catalyzed nitroalkene activation and sequential intermolecular condensation with aldehydes and ylides. Application of camphor‐derived chiral sulfur ylides gave the enantiomeric‐enriched isoxazoline‐N‐oxides in excellent yields and stereoselectivity. Simple transformations

  异恶唑啉N氧化物的转化：据报道，通过仲胺Lewis碱催化的硝基烯烃活化以及与醛和酰基化物的分子间缩合，简明地合成了异恶唑啉N氧化物。樟脑衍生的手性硫基化物的应用可得到对映异构体富集的异恶唑啉N-氧化物，具有出色的收率和立体选择性。异恶唑啉-N-氧化物的简单转化导致在四个步骤中以克级合成（-）-clausenamide类似物，并具有出色的立体化学控制（请参见方案）。
• Synthesis and activity in enhancing long-term potentiation (LTP) of clausenamide stereoisomers
  作者：Zhiqiang Feng、Xingzhou Li、Guojun Zheng、Liang Huang

  DOI：10.1016/j.bmcl.2009.03.018

  日期：2009.4

  Clausenamide, isolated from aqueous extract of dry leaves of Clausena lansium, a Chinese folk medicine, was found to have potent activity in enhancing LTP and show nootropic activity in animal tests. In order to discovery more potent stereoisomers and to analyze the relationship of structure-activity, the synthesis of 16 (8 pairs) optically pure stereoisomers of clausenamide with four chiral centers was achieved. The results of LTP assay showed that the nootropic activity of the stereoisomers of clausenamide is closely related to the configuration of stereoisomers. (C) 2009 Elsevier Ltd. All rights reserved.