(+)-(2R,3S)-7-chloro-2-(3-chloro-propyl)-3-((S)-2-methyl-propane-2-sulfinylamino)-heptanoic acid phenyl ester | 1315314-30-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-(2R,3S)-7-chloro-2-(3-chloro-propyl)-3-((S)-2-methyl-propane-2-sulfinylamino)-heptanoic acid phenyl ester
• 英文别名: phenyl (2R,3S)-3-[[(S)-tert-butylsulfinyl]amino]-7-chloro-2-(3-chloropropyl)heptanoate
• CAS: 1315314-30-7
• 化学式: C₂₀H₃₁Cl₂NO₃S
• 分子量: 436.443
• InChiKey: FOUVZDNJHLNDDG-UHMYUZELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-(2R,3S)-7-chloro-2-(3-chloro-propyl)-3-((S)-2-methyl-propane-2-sulfinylamino)-heptanoic acid phenyl ester 在 盐酸 、 potassium carbonate 、 sodium iodide 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 17.25h， 生成 (-)-(1R,9aS)-octahydro-quinolizine-1-carboxylic acid phenyl ester
  参考文献：
  名称：

  Total Syntheses of (−) Epilupinine and (−)-Tashiromine Using Imino-Aldol Reactions

  摘要：

  Short routes to enantiomerically pure indolizidine and quinolizidine alkaloids have been developed using imino-aldol reactions of enolates derived from phenyl 5-chlorovalerate. High levels of syn selectivity (dr similar to 13-16:1) were obtained using lithium enolates of phenyl esters In combination with tert-butylsulfinyl imines. The imino-aldol adducts were deprotected and cyclized to afford (-)-epilupinine ((-)-2) and (-)-tashiromine ((-)-1) in two further steps.

  DOI：

  10.1021/ol2015048
• 作为产物：
  描述：

  5-氯戊醛 在 copper(II) sulfate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 (+)-(2R,3S)-7-chloro-2-(3-chloro-propyl)-3-((S)-2-methyl-propane-2-sulfinylamino)-heptanoic acid phenyl ester
  参考文献：
  名称：

  Total Syntheses of (−) Epilupinine and (−)-Tashiromine Using Imino-Aldol Reactions

  摘要：

  Short routes to enantiomerically pure indolizidine and quinolizidine alkaloids have been developed using imino-aldol reactions of enolates derived from phenyl 5-chlorovalerate. High levels of syn selectivity (dr similar to 13-16:1) were obtained using lithium enolates of phenyl esters In combination with tert-butylsulfinyl imines. The imino-aldol adducts were deprotected and cyclized to afford (-)-epilupinine ((-)-2) and (-)-tashiromine ((-)-1) in two further steps.

  DOI：

  10.1021/ol2015048

文献信息

• Total Syntheses of (−) Epilupinine and (−)-Tashiromine Using Imino-Aldol Reactions
  作者：Amanda C. Cutter、Iain R. Miller、John F. Keily、Richard K. Bellingham、Mark E. Light、Richard C. D. Brown

  DOI：10.1021/ol2015048

  日期：2011.8.5

  Short routes to enantiomerically pure indolizidine and quinolizidine alkaloids have been developed using imino-aldol reactions of enolates derived from phenyl 5-chlorovalerate. High levels of syn selectivity (dr similar to 13-16:1) were obtained using lithium enolates of phenyl esters In combination with tert-butylsulfinyl imines. The imino-aldol adducts were deprotected and cyclized to afford (-)-epilupinine ((-)-2) and (-)-tashiromine ((-)-1) in two further steps.