methyl (7R)-7-[(S)-N-benzyloxycarbonylpyrrolidin-2-yl]-7-hydroxy-5-oxoheptanoate | 868285-34-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (7R)-7-[(S)-N-benzyloxycarbonylpyrrolidin-2-yl]-7-hydroxy-5-oxoheptanoate
• 英文别名: benzyl (2S)-2-[(1R)-1-hydroxy-7-methoxy-3,7-dioxoheptyl]pyrrolidine-1-carboxylate
• CAS: 868285-34-1
• 化学式: C₂₀H₂₇NO₆
• 分子量: 377.437
• InChiKey: VKOGLGMRLOVVQU-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (7R)-7-[(S)-N-benzyloxycarbonylpyrrolidin-2-yl]-7-hydroxy-5-oxoheptanoate 在 palladium dihydroxide 正丁基锂 、 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 dimethyl 5-[(1R,3S,7aS)-1-(1-ethoxyethoxy)hexahydro-1H-pyrrolizin-3-yl]-2-oxopentanephosphonate
  参考文献：
  名称：

  Structure Revision and Syntheses of Epohelmins A and B

  摘要：

  Epohelmins A (24) and B (26) have been reassigned as pyrrolizidin-1-ols, rather than the proposed 9-oxa-4-azabicyclo[6.1.0]nonane structures 1 and 2, respectively. Syntheses of epohelmin A (24) (eight steps, 52% overall yield) and epohelmin B (26) (11 steps, 43% overall yield) have been achieved starting from N-Cbz-(S)-prolinal (9) and ortho ester ketone 17 using a stereoselective aldol reaction and a stereoselective reductive cyclization as the key steps.

  DOI：

  10.1021/ol0516061
• 作为产物：
  描述：

  (2S)-N-苄氧羰基-2-吡咯烷甲醛 在 正丁基锂 、 溶剂黄146 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 7.0h， 生成 methyl (7R)-7-[(S)-N-benzyloxycarbonylpyrrolidin-2-yl]-7-hydroxy-5-oxoheptanoate
  参考文献：
  名称：

  Structure Revision and Syntheses of Epohelmins A and B

  摘要：

  Epohelmins A (24) and B (26) have been reassigned as pyrrolizidin-1-ols, rather than the proposed 9-oxa-4-azabicyclo[6.1.0]nonane structures 1 and 2, respectively. Syntheses of epohelmin A (24) (eight steps, 52% overall yield) and epohelmin B (26) (11 steps, 43% overall yield) have been achieved starting from N-Cbz-(S)-prolinal (9) and ortho ester ketone 17 using a stereoselective aldol reaction and a stereoselective reductive cyclization as the key steps.

  DOI：

  10.1021/ol0516061

文献信息

• Structure Revision and Syntheses of Epohelmins A and B
  作者：Barry B. Snider、Xiaolei Gao

  DOI：10.1021/ol0516061

  日期：2005.9.1

  Epohelmins A (24) and B (26) have been reassigned as pyrrolizidin-1-ols, rather than the proposed 9-oxa-4-azabicyclo[6.1.0]nonane structures 1 and 2, respectively. Syntheses of epohelmin A (24) (eight steps, 52% overall yield) and epohelmin B (26) (11 steps, 43% overall yield) have been achieved starting from N-Cbz-(S)-prolinal (9) and ortho ester ketone 17 using a stereoselective aldol reaction and a stereoselective reductive cyclization as the key steps.