(2R,5R)-2-butyl-5-propylpyrrolidine trifluoroacetate | 1452487-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,5R)-2-butyl-5-propylpyrrolidine trifluoroacetate
• CAS: 1452487-97-6
• 化学式: C₂HF₃O₂*C₁₁H₂₃N
• 分子量: 283.334
• InChiKey: WOFMVVBRHJCKJA-NDXYWBNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2R,5R)-2-butyl-5-propylpyrrolidine trifluoroacetate 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以70%的产率得到trans-2-butyl-5-propylpyrrolidine
  参考文献：
  名称：

  Stereodivergent Access to Cis- and Trans-3,5-Disubstituted 1,4-Thiazane 1-Oxides by Cyclization of Homochiral β-Amino Sulfoxides and Sulfones. The Preparation of Isomeric Ant Venom Alkaloids

  摘要：

  Intramolecular conjugate additions of homochiral (E)-1-alkenyl 2-aminoalkyl sulfoxides and sulfones were investigated. The relative position of the 3,5-substituents of the resulting 1,4-thiazane oxides was found to be dependent on the oxidation state of the sulfur atom, demonstrating a simple and highly stereodivergent synthetic protocol. Selected cis- and trans-3,5-disubstituted 1,4-thiazane dioxides were converted to cis- and trans-2,5-disubstituted pyrrolidines, known ant venom alkaloids.

  DOI：

  10.1021/ol4023003
• 作为产物：
  描述：

  (S_S,2R)-1-((E)-1-hexenylsulfinyl)pentan-2-amine 在 1,2-二溴四氯乙烷 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 叔丁醇 为溶剂， -78.0~70.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 (2R,5R)-2-butyl-5-propylpyrrolidine trifluoroacetate 、 2-butyl-5-propylpyrrolidine;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  Stereodivergent Access to Cis- and Trans-3,5-Disubstituted 1,4-Thiazane 1-Oxides by Cyclization of Homochiral β-Amino Sulfoxides and Sulfones. The Preparation of Isomeric Ant Venom Alkaloids

  摘要：

  Intramolecular conjugate additions of homochiral (E)-1-alkenyl 2-aminoalkyl sulfoxides and sulfones were investigated. The relative position of the 3,5-substituents of the resulting 1,4-thiazane oxides was found to be dependent on the oxidation state of the sulfur atom, demonstrating a simple and highly stereodivergent synthetic protocol. Selected cis- and trans-3,5-disubstituted 1,4-thiazane dioxides were converted to cis- and trans-2,5-disubstituted pyrrolidines, known ant venom alkaloids.

  DOI：

  10.1021/ol4023003

文献信息

• Concise Synthesis of Pyrrolidine and Indolizidine Alkaloids by a Highly Convergent Three‐Component Reaction
  作者：Guillaume Lapointe、Kurt Schenk、Philippe Renaud

  DOI：10.1002/chem.201003137

  日期：2011.3.7

  The synthesis of pyrrolidine and indolizidine derivatives through radical carboazidation of alkenes with α‐iodoketones, followed by reductive amination, is described. When properly substituted, further lactamization afforded pyrrolizidinones in good yield. This carboazidation/reductive amination sequence was efficiently applied to the total synthesis of three different simple alkaloids, including (±)‐monomorine

  描述了通过烯烃与α-碘酮的自由基碳叠氮化反应，然后进行还原胺化反应，合成吡咯烷和吲哚并咪唑衍生物的方法。当适当地被取代时，进一步的内酰胺化以良好的产率提供了吡咯烷二酮。该碳叠氮化/还原胺化序列被有效地应用于包括（±）-monomorine I在内的三种不同简单生物碱的全合成。