3-butyl-5-propyloctahydroindolizine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: 3-butyl-5-propyloctahydroindolizine
• 英文别名: (-)-(3R,5S,8aS)-3-butyl-5-propylindolizidine；indrizidine 223AB；(3R,5S,8aS)-3-butyl-5-propyl-1,2,3,5,6,7,8,8a-octahydroindolizine
• 化学式: C₁₅H₂₉N
• 分子量: 223.402
• InChiKey: ONNRIWKYSUKBOB-ZNMIVQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  L-焦谷氨酸 在 palladium on activated charcoal sodium tetrahydroborate 、 重铬酸吡啶 、 正丁基锂 、 氯化亚砜 、 硫酸 、 氢气 、 四氯化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， -78.0~25.0 ℃ 、303.98 kPa 条件下， 反应 30.5h， 生成 3-butyl-5-propyloctahydroindolizine
  参考文献：
  名称：

  Asymmetric synthesis of 3,5-disubstituted indolizidines by intermolecular addition of an allylsilane on an N-acyliminium ion

  摘要：

  A diastereoselective synthesis of 3,5-disubstituted indolizidines based on an intermolecular addition of an allylsilane on an acyliminium ion derived from (S)-pyroglutamic acid is described. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of (-)-indolizidine 195B, (-)-indolizidine 223AB, (+)-monomorine and (-)-3-butyl-5-propyl indolizidine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.027

文献信息

• Reversal of diastereofacial selectivity in the nucleophilic addition reaction to chiral N-sulfinimine and application to the synthesis of indrizidine 223AB
  作者：Yuji Koriyama、Akihiro Nozawa、Ryuuichirou Hayakawa、Makoto Shimizu

  DOI：10.1016/s0040-4020(02)01250-4

  日期：2002.11

  Diastereoselective addition reaction of ester enolates and Grignard reagents to optically active N-sulfinimines was examined. Reversal of the diastereofacial selectivity was realized by using appropriate metal species, solvents and additives, and the β-amino esters (up to >98% de) and the homoallylic amines (up to >98% de) were obtained in good yields. β-Amino esters thus obtained were converted to

  考察了酯烯酸酯和格氏试剂对光学活性N-亚磺胺的非对映选择性加成反应。通过使用适当的金属种类，溶剂和添加剂，可以逆转非对映选择性，并以良好的收率获得了β-氨基酯（至多> 98％de）和均烯丙基胺（至多> 98％de）。由此获得的β-氨基酸酯被转化为有用的涉及（R）-高丝氨酸的β-氨基酸。还描述了在吲哚定生物碱的合成中的应用。
• ZELLER, EMMANUEL;GRIERSON, DAVID S., HETEROCYCLES., 27,(1988) N, C. 1575-1578
  作者：ZELLER, EMMANUEL、GRIERSON, DAVID S.

  DOI：——

  日期：——
• Asymmetric synthesis of 3,5-disubstituted indolizidines by intermolecular addition of an allylsilane on an N-acyliminium ion
  作者：Elisabeth Conchon、Yvonne Gelas-Mialhe、Roland Remuson

  DOI：10.1016/j.tetasy.2006.04.027

  日期：2006.4

  A diastereoselective synthesis of 3,5-disubstituted indolizidines based on an intermolecular addition of an allylsilane on an acyliminium ion derived from (S)-pyroglutamic acid is described. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of (-)-indolizidine 195B, (-)-indolizidine 223AB, (+)-monomorine and (-)-3-butyl-5-propyl indolizidine. (c) 2006 Elsevier Ltd. All rights reserved.