(1S,5R,7R)-4-Acryloyl-10,10-dimethyl-3-phenyl-3,4-diaza-tricyclo[5.2.1.0^1,5]decan-2-one | 263722-73-2

• 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)-4-Acryloyl-10,10-dimethyl-3-phenyl-3,4-diaza-tricyclo[5.2.1.0^1,5]decan-2-one
• 英文别名: (1S,5R,7R)-10,10-dimethyl-3-phenyl-4-prop-2-enoyl-3,4-diazatricyclo[5.2.1.01,5]decan-2-one
• CAS: 263722-73-2
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: MBFXNDMPHKKCBB-MUKKUYKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (1S,5R,7R)-4-Acryloyl-10,10-dimethyl-3-phenyl-3,4-diaza-tricyclo[5.2.1.0^1,5]decan-2-one 在 双氧水 、 尿素 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以20%的产率得到
  参考文献：
  名称：

  樟脑-烯酰基吡唑啉酮的非对映选择性环氧化

  摘要：

  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。

  DOI：

  10.1002/jccs.200300148
• 作为产物：
  描述：

  (S)-(+)-酮基蒎酸 在 sodium tetrahydroborate 、 氯化亚砜 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 11.5h， 生成 (1S,5R,7R)-4-Acryloyl-10,10-dimethyl-3-phenyl-3,4-diaza-tricyclo[5.2.1.0^1,5]decan-2-one
  参考文献：
  名称：

  Diastereoselective Baylis−Hillman Reactions:  The Design and Synthesis of a Novel Camphor-Based Chiral Auxiliary

  摘要：

  Reaction of chiral acryloylhydrazide 5 derived from novel auxiliary 4 with aldehydes in the presence of DABCO affords practical levels (up to 98% de) of beta-hydroxy-alpha-methylene carbonyl derivatives, and high optical purity of both diastereomers of 6a-d and 7a-d can be obtained by changing the solvent.

  DOI：

  10.1021/ol990315n

文献信息

• Diastereoselective [3+2] cycloadditions of a camphor-derived chiral N-acryloylhydrazide with nitrile oxides: the preparation of optically pure Δ2-isoxazolines
  作者：Kung-Shuo Yang、Jung-Chaing Lain、Chun-Hui Lin、Kwunmin Chen

  DOI：10.1016/s0040-4039(99)02316-3

  日期：2000.2

  Reaction of a novel chiral N-acryloylhydrazide with various nitrile oxides proceeded smoothly to afford the cycloadduct with high diastereoselectivity (99:1). The auxiliary can be easily removed from the cycloadducts under mild conditions.

  新型手性N-丙烯酰肼与各种腈氧化物的反应进行得很顺利，从而得到具有高非对映选择性（99：1）的环加合物。在温和的条件下，可以轻松地从环加合物中除去辅助剂。
• A Facile and Highly Diastereoselective Aziridination of Chiral Camphor <i>N</i>-Enoylpyrazolidinones with <i>N</i>-Aminophthalimide
  作者：Kung-Shuo Yang、Kwunmin Chen

  DOI：10.1021/jo005621p

  日期：2001.3.1

  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.
• Diastereoselective Baylis−Hillman Reactions:  The Design and Synthesis of a Novel Camphor-Based Chiral Auxiliary
  作者：Kung-Shuo Yang、Kwunmin Chen

  DOI：10.1021/ol990315n

  日期：2000.3.1

  Reaction of chiral acryloylhydrazide 5 derived from novel auxiliary 4 with aldehydes in the presence of DABCO affords practical levels (up to 98% de) of beta-hydroxy-alpha-methylene carbonyl derivatives, and high optical purity of both diastereomers of 6a-d and 7a-d can be obtained by changing the solvent.
• 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。