(1R,2S,2S)-(-)-N-[2-(tert-butyldimethylsilyloxy)-1-(3-[1,3]dioxolan-2-yl-propyl)-butyl]-N-(2-methoxymethyl-pyrrolidin-1-yl)-amine | 444564-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: (1R,2S,2S)-(-)-N-[2-(tert-butyldimethylsilyloxy)-1-(3-[1,3]dioxolan-2-yl-propyl)-butyl]-N-(2-methoxymethyl-pyrrolidin-1-yl)-amine
• 英文别名: (2S)-N-[(4R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-1-(1,3-dioxolan-2-yl)heptan-4-yl]-2-(methoxymethyl)pyrrolidin-1-amine
• CAS: 444564-15-2
• 化学式: C₂₂H₄₆N₂O₄Si
• 分子量: 430.704
• InChiKey: AIVIJOKQOLHNOA-ZCNNSNEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S,2S)-(-)-N-[2-(tert-butyldimethylsilyloxy)-1-(3-[1,3]dioxolan-2-yl-propyl)-butyl]-N-(2-methoxymethyl-pyrrolidin-1-yl)-amine 在 三氟化硼四氢呋喃络合物 、 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 19.0h， 生成 (1S)-1-[(2R)-2,3,4,5-tetrahydropyridin-2-yl]propan-1-ol
  参考文献：
  名称：

  Asymmetric synthesis and structural assignment of (−)-α-conhydrine

  摘要：

  The first asymmetric synthesis of the conium alkaloid (-)-alpha-conhydrine is reported. Starting from a protected glycol aldehyde hydrazone as chiral precusor, a short route based on our alpha-alkylation/1,2-addition methodology has been developed. After cleavage of the auxiliary and simultaneous deprotection, the concluding ring closure is accomplished under reductive amination conditions. The title compound is obtained in moderate overall yield and in excellent diastereo- and enantiomeric excess (d.e., e.e. >96%). Single-crystal X-ray crystallography as well as H-1 NMR NOE experiments confirm the expected relative and absolute (2R,7S)-configuration of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00066-6
• 作为产物：
  描述：

  2-(3-溴丙基)-1,3-二氧戊环 在 lithium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 生成 (1R,2S,2S)-(-)-N-[2-(tert-butyldimethylsilyloxy)-1-(3-[1,3]dioxolan-2-yl-propyl)-butyl]-N-(2-methoxymethyl-pyrrolidin-1-yl)-amine
  参考文献：
  名称：

  Asymmetric synthesis and structural assignment of (−)-α-conhydrine

  摘要：

  The first asymmetric synthesis of the conium alkaloid (-)-alpha-conhydrine is reported. Starting from a protected glycol aldehyde hydrazone as chiral precusor, a short route based on our alpha-alkylation/1,2-addition methodology has been developed. After cleavage of the auxiliary and simultaneous deprotection, the concluding ring closure is accomplished under reductive amination conditions. The title compound is obtained in moderate overall yield and in excellent diastereo- and enantiomeric excess (d.e., e.e. >96%). Single-crystal X-ray crystallography as well as H-1 NMR NOE experiments confirm the expected relative and absolute (2R,7S)-configuration of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00066-6

文献信息

• Asymmetric synthesis and structural assignment of (−)-α-conhydrine
  作者：Dieter Enders、Bert Nolte、Gerhard Raabe、Jan Runsink

  DOI：10.1016/s0957-4166(02)00066-6

  日期：2002.3

  The first asymmetric synthesis of the conium alkaloid (-)-alpha-conhydrine is reported. Starting from a protected glycol aldehyde hydrazone as chiral precusor, a short route based on our alpha-alkylation/1,2-addition methodology has been developed. After cleavage of the auxiliary and simultaneous deprotection, the concluding ring closure is accomplished under reductive amination conditions. The title compound is obtained in moderate overall yield and in excellent diastereo- and enantiomeric excess (d.e., e.e. >96%). Single-crystal X-ray crystallography as well as H-1 NMR NOE experiments confirm the expected relative and absolute (2R,7S)-configuration of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.