(+/-)-1-epi-207I

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: (+/-)-1-epi-207I
• 英文别名: (1S,4R,9aR)-1-ethyl-4-prop-2-enyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizine
• 化学式: C₁₄H₂₅N
• 分子量: 207.359
• InChiKey: NRZJZBQAXGAIHA-MELADBBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-羰基-4-(2-吡啶基)丁酸 在 bis-triphenylphosphine-palladium(II) chloride 、 1-氯-N,N,2-三甲基丙烯胺 、 palladium on activated charcoal 、 palladium 10% on activated carbon 、 氢气 、 双(三甲基硅烷基)氨基钾 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 、 1,2-二氯乙烷 、 甲苯 为溶剂， -78.0~80.0 ℃ 、303.99 kPa 条件下， 反应 79.67h， 生成 (+/-)-1-epi-207I
  参考文献：
  名称：

  Synthesis of Highly Oxidized Quinolizidine via Reduction of Acylpyridinium Cations, and Total Syntheses of Quinolizidines 207I and 1-epi-207I

  摘要：

  A new strategy for synthesizing quinolizidine skeletons by reductive cyclization via acylpyridinium cations was developed. Several functional groups, including carbonyl, silyl, and acetal, were tolerated under mild reaction conditions. The reaction was successfully extended to a one-pot synthesis of a bicyclic compound, and the synthetic strategy was applied to concise total syntheses of quinolizidines 207I and 1-epi-207I, without protecting groups.

  DOI：

  10.1021/ol300541u

文献信息

• Enantioselective, protecting group-free synthesis of 1S-ethyl-4-substituted quinolizidines
  作者：Mercedes Amat、Vladislav Semak、Carmen Escolano、Elies Molins、Joan Bosch

  DOI：10.1039/c2ob25392e

  日期：——

  A practical enantioselective protecting group-free four-step route to the key quinolizidinone 6 from phenylglycinol-derived bicyclic lactam 1 is reported. The Grignard addition reaction to 6 takes place stereoselectively to give 1-ethyl-4-substituted quinolizidines 4-epi-207I and 7–9. Following a similar synthetic sequence, 9a-epi-6 is also accessed. However, the addition of Grignard reagents to 9a-epi-6

  据报道，从苯甘醇衍生的双环内酰胺1到关键的喹喔啉酮6的实用的无对映选择性保护基的四步途径。格利雅加成反应向6立体选择性地进行，得到1-乙基-4-取代的喹oli嗪4- Epi - 207I和7-9。按照相似的合成顺序，还可以得到9a- Epi - 6。但是，将格氏试剂添加到9a- epi - 6上的方法是非立体选择性的。为了深入了解两个系列中不同的立体化学结果，对亚胺盐进行了理论计算已执行A和B。研究得出结论，氢化物的添加是决定最终产品构型的步骤，是以立体电子控制的方式发生的。理论研究与实验结果吻合。
• Synthesis of Highly Oxidized Quinolizidine via Reduction of Acylpyridinium Cations, and Total Syntheses of Quinolizidines <b>207I</b> and 1-<i>epi</i>-<b>207I</b>
  作者：Chihiro Tsukano、Atsuko Oimura、Iderbat Enkhtaivan、Yoshiji Takemoto

  DOI：10.1021/ol300541u

  日期：2012.4.6

  A new strategy for synthesizing quinolizidine skeletons by reductive cyclization via acylpyridinium cations was developed. Several functional groups, including carbonyl, silyl, and acetal, were tolerated under mild reaction conditions. The reaction was successfully extended to a one-pot synthesis of a bicyclic compound, and the synthetic strategy was applied to concise total syntheses of quinolizidines 207I and 1-epi-207I, without protecting groups.