(2R,3R)-3-hydroxy-2-(4-methoxybenzyl)pyrrolidine | 676449-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3R)-3-hydroxy-2-(4-methoxybenzyl)pyrrolidine
• 英文别名: 2α-(p-Methoxy-phenylmethyl)-3α-hydroxy-pyrrolidin；(2R,3R)-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-ol
• CAS: 676449-09-5
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: ROFYZTJJQWDYCX-VXGBXAGGSA-N

物化性质

• 熔点：
  261-263 °C
• 沸点：
  354.5±27.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-hydroxy-2-(4-methoxybenzyl)pyrrolidine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2R,3R)-1-(Benzyloxycarbonyl)-2-<(3-methoxyphenyl)-methyl>pyrrolidin-3-yl S-Methyl Xanthate
  参考文献：
  名称：

  Asymmetric intramolecular amidation of N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine. A new entry to chiral building blocks for the synthesis of biologically active nitrogen-containing compounds

  摘要：

  Sharpless reaction of racemic N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine (1) leads to both an asymmetric kinetic resolution to provide optically active 1, which was subsequently used for intramolecular amidomercuration, and asymmetric epoxidation followed by concomitant cyclization into optically active cis-3-hydroxy-2-(hydroxymethyl)pyrrolidine (3). Optically active 1 and 3 have been expediently used as chiral building blocks in the asymmetric synthesis of several biologically active natural products.

  DOI：

  10.1021/jo00001a045
• 作为产物：
  描述：

  tert-butyl (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[hydroxy-(4-methoxyphenyl)methyl]pyrrolidine-1-carboxylate 生成 (2R,3R)-3-hydroxy-2-(4-methoxybenzyl)pyrrolidine
  参考文献：
  名称：

  TAKAHATA, HIROKI;BANBA, YASUNORI;TAJIMA, MAYUMI;MOMOSE, TAKEFUMI, J. ORG. CHEM., 56,(1991) N, C. 240-245

  摘要：

  DOI：

文献信息

• TAKAHATA, HIROKI;BANBA, YASUNORI;TAJIMA, MAYUMI;MOMOSE, TAKEFUMI, J. ORG. CHEM., 56,(1991) N, C. 240-245
  作者：TAKAHATA, HIROKI、BANBA, YASUNORI、TAJIMA, MAYUMI、MOMOSE, TAKEFUMI

  DOI：——

  日期：——
• Asymmetric intramolecular amidation of N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine. A new entry to chiral building blocks for the synthesis of biologically active nitrogen-containing compounds
  作者：Hiroki Takahata、Yasunori Banba、Mayumi Tajima、Takefumi Momose

  DOI：10.1021/jo00001a045

  日期：1991.1

  Sharpless reaction of racemic N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine (1) leads to both an asymmetric kinetic resolution to provide optically active 1, which was subsequently used for intramolecular amidomercuration, and asymmetric epoxidation followed by concomitant cyclization into optically active cis-3-hydroxy-2-(hydroxymethyl)pyrrolidine (3). Optically active 1 and 3 have been expediently used as chiral building blocks in the asymmetric synthesis of several biologically active natural products.