phenyl (3S)-4-[(1S,5R,7R)-10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-4-yl]-3-hydroxy-2-methylidene-4-oxobutanoate | 682806-85-5

• 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: phenyl (3S)-4-[(1S,5R,7R)-10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-4-yl]-3-hydroxy-2-methylidene-4-oxobutanoate
• CAS: 682806-85-5
• 化学式: C₂₇H₂₈N₂O₅
• 分子量: 460.53
• InChiKey: CQRXGCBYTDYEIB-YMFVMPCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  87.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氨基邻苯二甲胺 、 phenyl (3S)-4-[(1S,5R,7R)-10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-4-yl]-3-hydroxy-2-methylidene-4-oxobutanoate 在 lead(IV) acetate 作用下， 以81%的产率得到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：

  7,7-dimethyl-2'-phenyl-pyrazol-3'-one-bicyclo[2.2.1]heptane 在 三乙烯二胺 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 1.17h， 生成 phenyl (3S)-4-[(1S,5R,7R)-10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-4-yl]-3-hydroxy-2-methylidene-4-oxobutanoate
  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

文献信息

• 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.