N-glyoxyloyl camphorpyrazolidinone | 682806-82-2

• 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: N-glyoxyloyl camphorpyrazolidinone
• 英文别名: (10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.0^1,5]dec-4-yl)-oxoacetaldehyde；2-[(1S,5R,7R)-10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-4-yl]-2-oxoacetaldehyde
• CAS: 682806-82-2
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: PCLLPVKDPGDNHW-DFHBCGBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-glyoxyloyl camphorpyrazolidinone 在 三乙烯二胺 、 lead(IV) acetate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 phenyl (2S)-2-[(1S)-2-[(1S,5R,7R)-10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-4-yl]-1-hydroxy-2-oxoethyl]-1-(1,3-dioxoisoindol-2-yl)aziridine-2-carboxylate
  参考文献：
  名称：

  Diastereoselective Baylis–Hillman reaction using N-glyoxyloyl camphorpyrazolidinone as an electrophile: synthesis of optically pure 2-hydroxy-3-methylene succinic acid derivative

  摘要：

  The camphorpyrazolidinone derived N-glyoxylate was efficiently prepared and used as an electrophile in the Baylis-Hillman reaction under classical DABCO catalyzed conditions. The corresponding 2-hydroxy-3-methylene succinic acid derivative was generally obtained with excellent diastereoselectivity and moderate chemical yields (51-75%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.001
• 作为产物：
  描述：

  草酰氯 、 7,7-dimethyl-2'-phenyl-pyrazol-3'-one-bicyclo[2.2.1]heptane 在 三正丁基氢锡 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 0.34h， 以82%的产率得到N-glyoxyloyl camphorpyrazolidinone
  参考文献：
  名称：

  Highly diastereoselective allylation and reduction of chiral camphor-derived α-ketoamides

  摘要：

  The diastercoselective allylation and reduction of camphor-derivcd alpha-ketoamides to give optically enriched a-hydroxyl amides with high to excellent stereoselectivities are described. Allylation was carried out using allyltributylstannane in the presence of a stoichiometric amount of a Lewis acid to afford the desired homoallylic alcohols in relatively high chemical yields (up to 98%) and stereoselectivities (LIP to 98% de). Diastereoselective reductions were performed with the relatively bulky hydride K-Selectride at -78 degrees C to give the corresponding a-hydroxy amides in excellent chemical yields (LIP to 98%) and stereoselectivities (up to 98% de). The absolute configuration of the new stereogenic center of the major diastereomer was established by X-ray crystallographic analysis. Finally, stereochemical induction and the Lewis acid dependent reversal of stereoselectivity is described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.01.011

文献信息

• Diastereoselective Three Component Reaction of<i>N</i>-Glyoxyloyl Camphorpyrazolidinone, Amine and Allyltributylstannane: Facile Synthesis of Homoallylic Amines
  作者：Chih-Liang Chang、Kwun-Min Chen

  DOI：10.1002/jccs.200700224

  日期：2007.12

  Diastereoselective allylation of imine derived from N-glyoxyloyl camphorpyrazolidinone and amines was treated with allyltributylstannane in the presence of triflic acid. The corresponding optically enriched homoallylic amines were obtained in reasonable to high material yields and with practical levels of stereoselectivity in 10 min at ambient temperature.

  在三氟甲磺酸存在下，用烯丙基三丁基锡烷处理衍生自 N-乙醛酰樟脑吡唑烷酮和胺的亚胺的非对映选择性烯丙基化。相应的光学富集的均烯丙基胺以合理至高的材料产率获得，并且在环境温度下在 10 分钟内具有实用水平的立体选择性。
• An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile
  作者：Jia-Fu Pan、Uppala Venkatesham、Kwunmin Chen

  DOI：10.1016/j.tetlet.2004.10.121

  日期：2004.12

  The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding alpha-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed. (C) 2004 Published by Elsevier Ltd.
• Diastereoselective Baylis–Hillman reaction using N-glyoxyloyl camphorpyrazolidinone as an electrophile: synthesis of optically pure 2-hydroxy-3-methylene succinic acid derivative
  作者：Jia-Fu Pan、Kwunmin Chen

  DOI：10.1016/j.tetlet.2004.02.001

  日期：2004.3

  The camphorpyrazolidinone derived N-glyoxylate was efficiently prepared and used as an electrophile in the Baylis-Hillman reaction under classical DABCO catalyzed conditions. The corresponding 2-hydroxy-3-methylene succinic acid derivative was generally obtained with excellent diastereoselectivity and moderate chemical yields (51-75%). (C) 2004 Elsevier Ltd. All rights reserved.
• Highly diastereoselective allylation and reduction of chiral camphor-derived α-ketoamides
  作者：Neelesh A. Kulkarni、Shy-Guey Wang、Li-Chen Lee、Huei Ru Tsai、Uppala Venkatesham、Kwunmin Chen

  DOI：10.1016/j.tetasy.2006.01.011

  日期：2006.2

  The diastercoselective allylation and reduction of camphor-derivcd alpha-ketoamides to give optically enriched a-hydroxyl amides with high to excellent stereoselectivities are described. Allylation was carried out using allyltributylstannane in the presence of a stoichiometric amount of a Lewis acid to afford the desired homoallylic alcohols in relatively high chemical yields (up to 98%) and stereoselectivities (LIP to 98% de). Diastereoselective reductions were performed with the relatively bulky hydride K-Selectride at -78 degrees C to give the corresponding a-hydroxy amides in excellent chemical yields (LIP to 98%) and stereoselectivities (up to 98% de). The absolute configuration of the new stereogenic center of the major diastereomer was established by X-ray crystallographic analysis. Finally, stereochemical induction and the Lewis acid dependent reversal of stereoselectivity is described. (c) 2006 Elsevier Ltd. All rights reserved.