(S)-1-tosyl-4-tributylstannyl-4,5-didehydroproline ethyl ester | 872094-07-0

• 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: (S)-1-tosyl-4-tributylstannyl-4,5-didehydroproline ethyl ester
• 英文别名: ethyl (2S)-1-(4-methylphenyl)sulfonyl-4-tributylstannyl-2,3-dihydropyrrole-2-carboxylate
• CAS: 872094-07-0
• 化学式: C₂₆H₄₃NO₄SSn
• 分子量: 584.408
• InChiKey: PREZZPOZIUYTLK-AHJYMZSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-tosyl-4-tributylstannyl-4,5-didehydroproline ethyl ester 在 碘 作用下， 以 甲苯 为溶剂， 反应 0.08h， 生成 (S)-4-iodo-1-tosyl-4,5-didehydroproline ethyl ester
  参考文献：
  名称：

  One-pot synthesis of chiral dehydroproline esters: [3+2]-type cycloaddition reaction of allenylstannane and α-imino ester

  摘要：

  An enantioselective [3+2]-type cycloaddition of allenylstannane and alpha-imino ester was developed. Synthetic utility of the 4stannyldehydroproline ester intermediate was demonstrated: iodine oxidation and Stille coupling reaction of the intermediate afforded optically active 4-iodo- and 4-aryldehydroproline esters in good yields and in high ees, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.018
• 作为产物：
  描述：

  1,2-丙二烯三正丁基锡 、 ethyl (N-tosylimino)acetate 在 tetrakis(acetonitrile)copper(I) perchlorate 、 (±)-2,2 '-二(二-对甲苯基膦)-1,1 '-联萘 silica gel 作用下， 以 甲苯 、 正己烷 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 (R)-1-tosyl-4,5-didehydroproline ethyl ester 、 (S)-1-tosyl-4,5-didehydroproline ethyl ester 、 (S)-1-tosyl-4-tributylstannyl-4,5-didehydroproline ethyl ester
  参考文献：
  名称：

  One-pot synthesis of chiral dehydroproline esters: [3+2]-type cycloaddition reaction of allenylstannane and α-imino ester

  摘要：

  An enantioselective [3+2]-type cycloaddition of allenylstannane and alpha-imino ester was developed. Synthetic utility of the 4stannyldehydroproline ester intermediate was demonstrated: iodine oxidation and Stille coupling reaction of the intermediate afforded optically active 4-iodo- and 4-aryldehydroproline esters in good yields and in high ees, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.018