(R)-3-(1-Hydroxy-cyclopentyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester | 184032-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (R)-3-(1-Hydroxy-cyclopentyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (3R)-3-(1-hydroxycyclopentyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 184032-81-3
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: WRZLGIPFLJYTKW-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-(1-Hydroxy-cyclopentyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以83%的产率得到(R)-1'-<1,2,3,4-tetrahydroisochinolin-3-yl>cyclopentanol
  参考文献：
  名称：

  Enantioselective Catalytic Borane Reduction of Prochiral Ketones: Synthesis and Application of New Rigid β-Amino Alcohols with a Cycloalkanol Subunit

  摘要：

  Enantiocontrolled reduction of prochiral ketones with borane in the presence of new enantiomerically pure bi- and tricyclic beta-sec-amino alcohols 2-5 as stereodifferentiating catalysts afforded the optically active corresponding secondary alcohols in moderate to excellent (up to 98 % op) optical yields.

  DOI：

  10.1080/00397919608003849
• 作为产物：
  描述：

  1,3-二溴丙烷 、 N-Boc-(D)-Tic methyl ester 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 以49%的产率得到(R)-3-(1-Hydroxy-cyclopentyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantioselective Catalytic Borane Reduction of Prochiral Ketones: Synthesis and Application of New Rigid β-Amino Alcohols with a Cycloalkanol Subunit

  摘要：

  Enantiocontrolled reduction of prochiral ketones with borane in the presence of new enantiomerically pure bi- and tricyclic beta-sec-amino alcohols 2-5 as stereodifferentiating catalysts afforded the optically active corresponding secondary alcohols in moderate to excellent (up to 98 % op) optical yields.

  DOI：

  10.1080/00397919608003849

文献信息

• Synthesis and application of new β-amino alcohols based on the octahydro-cyclopenta[b]pyrrole system in the catalytic enantioselective addition of diethylzinc to benzaldehyde
  作者：Jörg Wilken、Michael Kossenjans、Harald Gröger、Jürgen Martens

  DOI：10.1016/s0957-4166(97)00201-2

  日期：1997.6

  Starting from an industrial waste material, the synthesis of a series of new, artificial beta-amino alcohol structures (all-R)-6-10 and 13-16 based on the octahydrocyclopenta[b]pyrrole system is presented. These structures were also the subject of studies aimed at developing effective catalysts for enantioselective alkylation by diethylzinc. Attention was focussed on stereochemical and steric aspects of the catalyst (-precursor) structure. Potent chiral ligands have been developed reaching excellent enantioselectivities, e.g. op-values up to 99% with predominant formation of the (R)-configurated alkylation products. (C) 1997 Elsevier Science Ltd.