(-)-3S,4S,5R-cisneoclausenamidone | 608122-69-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-3S,4S,5R-cisneoclausenamidone
• 英文别名: (3S,4S,5R)-5-benzoyl-3-hydroxy-1-methyl-4-phenylpyrrolidin-2-one
• CAS: 608122-69-6
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: XBQHNXLCOAIENZ-UXLLHSPISA-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：

  (-)-3S,4S,5R-cisneoclausenamidone 在 sodium tetrahydroborate 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (1R,3R,4R,7R)-5-Methyl-3,7-diphenyl-2-oxa-5-aza-bicyclo[2.2.1]heptan-6-one
  参考文献：
  名称：

  A concise total synthesis of (−)-dehydroclausenamide utilizing the novel formation of cis-epoxide as the key step

  摘要：

  The asymmetric total synthesis of (-)-dehydroclausenamide 1 was accomplished through a concise and efficient synthetic route employing as the key step the novel formation of cis-epoxy amide 7, which was resulted from the reaction of starting material 4 bearing an optically pure erythro vicinal diol unit with 5H-3-oxa-octafluoro pentanesulfonyl fluoride (HCF2CF2OCF2CF2SO2F) in the presence of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.229
• 作为产物：
  描述：

  (2R,3S)-2,3-Dihydroxy-N-<(2'RS)-2'-hydroxy-2'-phenylethyl>-N-methylpropanamide 在 重铬酸吡啶 、 四甲基氢氧化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 1,1,2,2-四氟-2-(1,1,2,2-四氟乙氧基)乙烷磺酰基氟化物 作用下， 以 二氯甲烷 为溶剂， 生成 (-)-3S,4S,5R-cisneoclausenamidone
  参考文献：
  名称：

  A concise total synthesis of (−)-dehydroclausenamide utilizing the novel formation of cis-epoxide as the key step

  摘要：

  The asymmetric total synthesis of (-)-dehydroclausenamide 1 was accomplished through a concise and efficient synthetic route employing as the key step the novel formation of cis-epoxy amide 7, which was resulted from the reaction of starting material 4 bearing an optically pure erythro vicinal diol unit with 5H-3-oxa-octafluoro pentanesulfonyl fluoride (HCF2CF2OCF2CF2SO2F) in the presence of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.229

文献信息

• Synthesis of isoxazoline N-oxides and its application in the formal synthesis of dehydroclausenamide
  作者：Chun-Yin Zhu、Xiu-Li Sun、Xian-Ming Deng、Jun-Cheng Zheng、Yong Tang

  DOI：10.1016/j.tet.2008.03.075

  日期：2008.6

  A protocol for the synthesis of isoxazoline N-oxides and its application in the formal synthesis of dehydroclausenamide are described. Sulfonium salt 1 reacts with substituted nitroalkenes smoothly to generate isoxazoline N-oxides in high to excellent yields with dr higher than 99/1. Its asymmetric version has been developed by using cinchona alkaloid-derived ammonium salts 6a and 6b instead of sulfonium

  描述了用于合成异恶唑啉N-氧化物的方案及其在脱氢clausenamide的形式合成中的应用。salt盐1与取代的硝基烯烃平滑反应，以高至极好的收率（高于99/1）生成异恶唑啉N-氧化物。它的不对称形式是通过使用金鸡纳生物碱衍生的铵盐6a和6b代替sulf盐1而开发的，ee值高于96％。该方法也已经成功地用于脱氢克柳酰胺的形式合成。
• Use of optically active clausenamides for the preparation of pharmaceutical compositions, pharmaceutical compositions containing the same
  申请人：INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF MEDICAL SCIENCES

  公开号：EP1348696B1

  公开（公告）日：2012-02-01
• 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.
• A concise total synthesis of (−)-dehydroclausenamide utilizing the novel formation of cis-epoxide as the key step
  作者：Zhaohua Yan、Jianqiang Wang、Weisheng Tian

  DOI：10.1016/j.tetlet.2003.09.229

  日期：2003.12

  The asymmetric total synthesis of (-)-dehydroclausenamide 1 was accomplished through a concise and efficient synthetic route employing as the key step the novel formation of cis-epoxy amide 7, which was resulted from the reaction of starting material 4 bearing an optically pure erythro vicinal diol unit with 5H-3-oxa-octafluoro pentanesulfonyl fluoride (HCF2CF2OCF2CF2SO2F) in the presence of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU). (C) 2003 Elsevier Ltd. All rights reserved.