(1S,5R,7R)-10,10-dimethyl-4-(3-methylbut-2-enoyl)-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-2-one | 332923-18-9

• 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: (1S,5R,7R)-10,10-dimethyl-4-(3-methylbut-2-enoyl)-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-2-one
• CAS: 332923-18-9
• 化学式: C₂₁H₂₆N₂O₂
• 分子量: 338.45
• InChiKey: QRVWYBFDXWHTJA-CEQIKUNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氨基邻苯二甲胺 、 (1S,5R,7R)-10,10-dimethyl-4-(3-methylbut-2-enoyl)-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-2-one 在 lead(IV) acetate 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以92%的产率得到2-[(3R)-3-[(1S,5R,7R)-10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decane-4-carbonyl]-2,2-dimethylaziridin-1-yl]isoindole-1,3-dione
  参考文献：
  名称：

  A Facile and Highly Diastereoselective Aziridination of Chiral Camphor N-Enoylpyrazolidinones with N-Aminophthalimide

  摘要：

  Reaction of various chiral camphor N-enoylprazalidinones 2a-g with N-aminophthalimide in the presence of lead tetraacetate in CH2Cl2 proceed smoothly afford the corresponding N-phthalimidoaziridines (3a-e, 4f-g) with excellent material yields (86-95%) at room temperature in 5 min. High levels of diastereoselectivities (up to >95:5 dr) were obtained. The solvent effect was investigated, and the auxilary can be easily recovered in high yields under mild reaction conditions.

  DOI：

  10.1021/jo005621p
• 作为产物：
  描述：

  (1S,5R,7R)-4-Acryloyl-10,10-dimethyl-3-phenyl-3,4-diaza-tricyclo[5.2.1.0^1,5]decan-2-one 在 lead(IV) acetate 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.58h， 生成 (1S,5R,7R)-10,10-dimethyl-4-(3-methylbut-2-enoyl)-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-2-one
  参考文献：
  名称：

  A Facile and Highly Diastereoselective Aziridination of Chiral Camphor N-Enoylpyrazolidinones with N-Aminophthalimide

  摘要：

  Reaction of various chiral camphor N-enoylprazalidinones 2a-g with N-aminophthalimide in the presence of lead tetraacetate in CH2Cl2 proceed smoothly afford the corresponding N-phthalimidoaziridines (3a-e, 4f-g) with excellent material yields (86-95%) at room temperature in 5 min. High levels of diastereoselectivities (up to >95:5 dr) were obtained. The solvent effect was investigated, and the auxilary can be easily recovered in high yields under mild reaction conditions.

  DOI：

  10.1021/jo005621p

文献信息

• Diastereoselective Epoxidation of Camphor<i>N</i>-Enoylpyrazolidinones
  作者：Chai Ling Fan、Gondi Sudershan Reddy、Kwunmin Chen

  DOI：10.1002/jccs.200300148

  日期：2003.10

  Reaction of camphor N-enoylpyrazolidinones (1a-j) with various oxidants, in particular UHP/TFAA afford chiral epoxides with a wide range of stereoselectivities (up to > 90% de).

  樟脑 N-烯酰基吡唑烷酮 (1a-j) 与各种氧化剂，特别是 UHP/TFAA 的反应提供了具有广泛立体选择性（高达 > 90% de）的手性环氧化物。
• Epoxidation of Chiral Camphor <i>N</i>-Enoylpyrazolidinones with Methyl(trifluoromethyl)dioxirane and Urea Hydrogen Peroxide/Acid Anhydride:  Reversal of Stereoselectivity
  作者：Chai Ling Fan、Wei-Der Lee、Nai-Wei Teng、Ying-Chieh Sun、Kwunmin Chen

  DOI：10.1021/jo034807w

  日期：2003.12.1

  Both diastereomeric isomers of epoxides with high optical purity are obtained when camphor N-methacryloylpyrazolidinone (1a) and N-tigloylpyrazolidinone (1b) are treated with a urea hydrogen peroxide/TFAA and methyl(trifluoromethyl)dioxirane, respectively.

  当分别用过氧化氢尿素/ TFAA和甲基（三氟甲基）二环氧乙烷处理樟脑N-甲基丙烯酰基吡唑烷二酮（1a）和N-tigloyl吡唑烷二酮（1b）时，可获得具有高光学纯度的两种非对映异构体。