(R)-1-[6-(2,6-dimethylphenyl)pyridin-2-yl]ethyl methanesulfonate | 428514-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (R)-1-[6-(2,6-dimethylphenyl)pyridin-2-yl]ethyl methanesulfonate
• 英文别名: [(1R)-1-[6-(2,6-dimethylphenyl)pyridin-2-yl]ethyl] methanesulfonate
• CAS: 428514-90-3
• 化学式: C₁₆H₁₉NO₃S
• 分子量: 305.398
• InChiKey: CYSNCLSJLYQGIY-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-[(二苯基膦)甲基]吡咯烷 、 (R)-1-[6-(2,6-dimethylphenyl)pyridin-2-yl]ethyl methanesulfonate 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以86%的产率得到(2S)-1-[(1S)-1-[6-(2,6-dimethylphenyl)pyridin-2-yl]ethyl]-2-[(diphenylphosphanyl)methyl]pyrrolidine
  参考文献：
  名称：

  Preparation of new chiral pyridine–phosphine ligands and their Pd-catalyzed asymmetric allylic alkylations

  摘要：

  Enantiomerically pure 2-(diphenylphosphino)methyl-N-[1-(2-pyridinyl)ethyl]pyrrolidines 1 and 2 have been prepared by the stereospecific substitution of enantiomerically pure 1-(2-pyridinyl)ethyl methanesulfonate 6 with enantiomerically pure 2-(diphenylphosphino)methylpyrrolidine. Asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate 11 with dimethyl malonate sodium salt using the (S,S)-ligand 1 affords the (R)-product 12 with up to 86% e.e. in good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00535-3
• 作为产物：
  描述：

  (R)-1-(6-bromopyridin-2-yl)ethanol 在 四(三苯基膦)钯 4-二甲氨基吡啶 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 50.5h， 生成 (R)-1-[6-(2,6-dimethylphenyl)pyridin-2-yl]ethyl methanesulfonate
  参考文献：
  名称：

  Preparation of new chiral pyridine–phosphine ligands and their Pd-catalyzed asymmetric allylic alkylations

  摘要：

  Enantiomerically pure 2-(diphenylphosphino)methyl-N-[1-(2-pyridinyl)ethyl]pyrrolidines 1 and 2 have been prepared by the stereospecific substitution of enantiomerically pure 1-(2-pyridinyl)ethyl methanesulfonate 6 with enantiomerically pure 2-(diphenylphosphino)methylpyrrolidine. Asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate 11 with dimethyl malonate sodium salt using the (S,S)-ligand 1 affords the (R)-product 12 with up to 86% e.e. in good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00535-3

文献信息

• Preparation of new chiral pyridine–phosphine ligands and their Pd-catalyzed asymmetric allylic alkylations
  作者：Jun'ichi Uenishi、Masahiro Hamada

  DOI：10.1016/s0957-4166(01)00535-3

  日期：2001.11

  Enantiomerically pure 2-(diphenylphosphino)methyl-N-[1-(2-pyridinyl)ethyl]pyrrolidines 1 and 2 have been prepared by the stereospecific substitution of enantiomerically pure 1-(2-pyridinyl)ethyl methanesulfonate 6 with enantiomerically pure 2-(diphenylphosphino)methylpyrrolidine. Asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate 11 with dimethyl malonate sodium salt using the (S,S)-ligand 1 affords the (R)-product 12 with up to 86% e.e. in good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.