(2S*,2'R*)-2-(1-methylallyl)pyrrolidine

• 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: (2S*,2'R*)-2-(1-methylallyl)pyrrolidine
• 英文别名: (2S)-2-[(2R)-but-3-en-2-yl]pyrrolidine
• 化学式: C₈H₁₅N
• 分子量: 125.214
• InChiKey: FASCWLWEGJNYRR-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S*,2'R*)-2-(1-methylallyl)pyrrolidine 在 氯化亚砜 、 tetra-n-propyl-diborane 、 硫酸 、 双氧水 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 (+/-)-pseudoheliotridane
  参考文献：
  名称：

  Synthesis of (±)-pseudoheliotridane by allylboration of 1-pyrroline

  摘要：

  Reaction of tricrotylborane with 1-pyrroline proceeds stereoselectively to give (1R*,1'S*)-2-(1-methylallyl)pyrrolidine. The latter was converted to the pyrrolizidine alkaloid (+/-)-pseudoheliotridane through hydroboration-oxidation-intra molecular cyclization.

  DOI：

  10.1007/bf02495581
• 作为产物：
  描述：

  3,4-二氢-2H-吡咯 、 tricrotylborane 在 三乙醇胺 作用下， 生成 (2S*,2'R*)-2-(1-methylallyl)pyrrolidine
  参考文献：
  名称：

  Synthesis of (±)-pseudoheliotridane by allylboration of 1-pyrroline

  摘要：

  Reaction of tricrotylborane with 1-pyrroline proceeds stereoselectively to give (1R*,1'S*)-2-(1-methylallyl)pyrrolidine. The latter was converted to the pyrrolizidine alkaloid (+/-)-pseudoheliotridane through hydroboration-oxidation-intra molecular cyclization.

  DOI：

  10.1007/bf02495581

文献信息

• Ruthenium-Catalyzed C–C Coupling of Amino Alcohols with Dienes via Transfer Hydrogenation: Redox-Triggered Imine Addition and Related Hydroaminoalkylations
  作者：Te-Yu Chen、Ryosuke Tsutsumi、T. Patrick Montgomery、Ivan Volchkov、Michael J. Krische

  DOI：10.1021/ja5130258

  日期：2015.2.11

  Ruthenium-catalyzed hydrogen transfer from 4-aminobutanol to butadiene results in the pairwise generation of 3,4-dihydro-2H-pyrrole and an allylruthenium complex, which combine to form products of imine anti-crotylation. In couplings of 1-substituted-1,3-dienes, novel C2 regioselectivity is observed. As corroborated by deuterium labeling studies, kinetically preferred hydrometalation of the terminal olefin of the 1-substituted-1,3-diene delivers a 1,1-disubstituted p-allylruthenium complex that isomerizes to a thermodynamically more stable monosubstituted p-allylruthenium complex, which undergoes imine addition with allylic inversion through a closed transition structure. Direct ruthenium-catalyzed diene hydroaminoalkylations with pyrrolidine also are described.
• Synthesis of (±)-pseudoheliotridane by allylboration of 1-pyrroline
  作者：M. E. Gurskii、T. V. Potapova、Yu. N. Bubnov

  DOI：10.1007/bf02495581

  日期：1998.7

  Reaction of tricrotylborane with 1-pyrroline proceeds stereoselectively to give (1R*,1'S*)-2-(1-methylallyl)pyrrolidine. The latter was converted to the pyrrolizidine alkaloid (+/-)-pseudoheliotridane through hydroboration-oxidation-intra molecular cyclization.

表征谱图