2-benzyloxymethyl-4-phenyl-1-(4-methylphenylsulfonyl)pyrrolidin-3-one | 920035-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzyloxymethyl-4-phenyl-1-(4-methylphenylsulfonyl)pyrrolidin-3-one
• 英文别名: (2R,4S)-1-(4-methylphenyl)sulfonyl-4-phenyl-2-(phenylmethoxymethyl)pyrrolidin-3-one
• CAS: 920035-13-8
• 化学式: C₂₅H₂₅NO₄S
• 分子量: 435.544
• InChiKey: YFJOCFVMZSEFKB-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-benzyloxymethyl-4-phenyl-1-(4-methylphenylsulfonyl)pyrrolidin-3-one 在 palladium on activated charcoal 二异丁基氢化铝 、 氢气 作用下， 以 四氢呋喃 、 正己烷 、 甲醇 为溶剂， 反应 13.0h， 生成 (2R,3R,4S)-2-hydroxymethyl-4-phenyl-1-(4-methylphenylsulfonyl)pyrrolidin-3-ol 、 (2R,3S,4S)-2-hydroxymethyl-4-phenyl-1-(4-methylphenylsulfonyl)pyrrolidin-3-ol
  参考文献：
  名称：

  Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols

  摘要：

  Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols has been established starting from 2-benzyloxymethylpyrrolidin-2-one framework, which is derived from commercially available trans-(2S,4R)-4-hydroxyproline. The single diastereorner having a trans-cis relative configuration with C-2 and C-3 and C-3 and C-4 is constructed in two one-pot functional group transformations of Grignard addition/dehydration and epoxidation/isomerization as the key steps in moderate yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.002
• 作为产物：
  描述：

  (2S,4R)-1-(4-methylphenyl)sulfonyl-2-hydroxymethyl-4-(t-butyldimethylsilanyloxy)pyrrolidine 在 三氟化硼乙醚 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.83h， 生成 2-benzyloxymethyl-4-phenyl-1-(4-methylphenylsulfonyl)pyrrolidin-3-one
  参考文献：
  名称：

  Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols

  摘要：

  Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols has been established starting from 2-benzyloxymethylpyrrolidin-2-one framework, which is derived from commercially available trans-(2S,4R)-4-hydroxyproline. The single diastereorner having a trans-cis relative configuration with C-2 and C-3 and C-3 and C-4 is constructed in two one-pot functional group transformations of Grignard addition/dehydration and epoxidation/isomerization as the key steps in moderate yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.002

文献信息

• Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols
  作者：Meng-Yang Chang、Chun-Yu Lin、Tsun-Cheng Wu

  DOI：10.1016/j.tet.2006.10.002

  日期：2006.12

  Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols has been established starting from 2-benzyloxymethylpyrrolidin-2-one framework, which is derived from commercially available trans-(2S,4R)-4-hydroxyproline. The single diastereorner having a trans-cis relative configuration with C-2 and C-3 and C-3 and C-4 is constructed in two one-pot functional group transformations of Grignard addition/dehydration and epoxidation/isomerization as the key steps in moderate yield. (c) 2006 Elsevier Ltd. All rights reserved.