3-[(2S)-2-ethenyl-5-oxo-1-prop-2-enylpiperidin-2-yl]propanal | 1416404-18-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 3-[(2S)-2-ethenyl-5-oxo-1-prop-2-enylpiperidin-2-yl]propanal
• CAS: 1416404-18-6
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: GJIOHKYNXSMZOB-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(2S)-2-ethenyl-5-oxo-1-prop-2-enylpiperidin-2-yl]propanal 在 titanium(IV) isopropylate 、 盐酸 、 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 水 、 四丁基碘化铵 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 mineral oil 为溶剂， 反应 35.16h， 生成 (5S,7S,10aS)-8-(benzyloxy)-5-(4-methoxybenzyl)-7,8,9,10-tetrahydro-3H-7,10a-methanopyrrolo[1,2-a]azocine-3,6(5H)-dione
  参考文献：
  名称：

  A Formal Enantioselective Total Synthesis of FR901483

  摘要：

  A formal enantioselective total synthesis of the potent immunosuppressant FR901483 (1) has been accomplished. Our approach features the use of chiron 6 as the starting material, the application of the one-pot amide reductive bisalkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diastereoselective intramolecular aldol reaction to build the bridged ring, and ring closing metathesis to form the 3-pyrrolin-2-one ring.

  DOI：

  10.1021/ol302165d
• 作为产物：
  描述：

  (3R,6R)-6-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-6-vinylpiperidin-3-ol 在 盐酸 、 草酰氯 、 水 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-[(2S)-2-ethenyl-5-oxo-1-prop-2-enylpiperidin-2-yl]propanal
  参考文献：
  名称：

  A Formal Enantioselective Total Synthesis of FR901483

  摘要：

  A formal enantioselective total synthesis of the potent immunosuppressant FR901483 (1) has been accomplished. Our approach features the use of chiron 6 as the starting material, the application of the one-pot amide reductive bisalkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diastereoselective intramolecular aldol reaction to build the bridged ring, and ring closing metathesis to form the 3-pyrrolin-2-one ring.

  DOI：

  10.1021/ol302165d

文献信息

• Enantioselective Total Syntheses of (−)-FR901483 and (+)-8-<i>epi</i>-FR901483
  作者：Hao-Hua Huo、Xiao-Er Xia、Hong-Kui Zhang、Pei-Qiang Huang

  DOI：10.1021/jo302362b

  日期：2013.1.18

  The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diaster-eoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.
• A Formal Enantioselective Total Synthesis of FR901483
  作者：Hao-Hua Huo、Hong-Kui Zhang、Xiao-Er Xia、Pei-Qiang Huang

  DOI：10.1021/ol302165d

  日期：2012.9.21

  A formal enantioselective total synthesis of the potent immunosuppressant FR901483 (1) has been accomplished. Our approach features the use of chiron 6 as the starting material, the application of the one-pot amide reductive bisalkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diastereoselective intramolecular aldol reaction to build the bridged ring, and ring closing metathesis to form the 3-pyrrolin-2-one ring.