(4R)-5-hydroxy-4-methoxy-1-[(4-methoxyphenyl)methyl]-5-[4-(oxan-2-yloxy)butyl]pyrrolidin-2-one | 1429302-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4R)-5-hydroxy-4-methoxy-1-[(4-methoxyphenyl)methyl]-5-[4-(oxan-2-yloxy)butyl]pyrrolidin-2-one
• CAS: 1429302-12-4
• 化学式: C₂₂H₃₃NO₆
• 分子量: 407.507
• InChiKey: OIIWTSNXTWMACQ-JSRJAPPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-5-hydroxy-4-methoxy-1-[(4-methoxyphenyl)methyl]-5-[4-(oxan-2-yloxy)butyl]pyrrolidin-2-one 在 ammonium cerium (IV) nitrate 、 三氟甲磺酸酐 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.2h， 生成 (4R,5S)-4-methoxy-2-(1H-pyrrol-2-yl)-6-oxa-1-azaspiro[4.5]dec-1-ene
  参考文献：
  名称：

  Spiroaminal model systems of the marineosins with final step pyrrole incorporation

  摘要：

  In this Letter, we describe a short, six step enantioselective route to spiroaminal lactam model systems reminiscent of marineosins A and B that has been developed starting from either (R)- or (S)-hydroxysuccinic acid, respectively, in similar to 9% overall yield. This route enables late stage incorporation of the pyrrole ring at C5 via nucleophilic displacement of an iminium triflate salt. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.059
• 作为产物：
  描述：

  (R)-3-hydroxy-1-(4-methoxybenzyl)pyrrolidine-2,5-dione 在 magnesium 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.5h， 生成 (4R)-5-hydroxy-4-methoxy-1-[(4-methoxyphenyl)methyl]-5-[4-(oxan-2-yloxy)butyl]pyrrolidin-2-one
  参考文献：
  名称：

  Spiroaminal model systems of the marineosins with final step pyrrole incorporation

  摘要：

  In this Letter, we describe a short, six step enantioselective route to spiroaminal lactam model systems reminiscent of marineosins A and B that has been developed starting from either (R)- or (S)-hydroxysuccinic acid, respectively, in similar to 9% overall yield. This route enables late stage incorporation of the pyrrole ring at C5 via nucleophilic displacement of an iminium triflate salt. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.059

文献信息

• Spiroaminal model systems of the marineosins with final step pyrrole incorporation
  作者：Joseph D. Panarese、Leah C. Konkol、Cynthia B. Berry、Brittney S. Bates、Leslie N. Aldrich、Craig W. Lindsley

  DOI：10.1016/j.tetlet.2013.02.059

  日期：2013.5

  In this Letter, we describe a short, six step enantioselective route to spiroaminal lactam model systems reminiscent of marineosins A and B that has been developed starting from either (R)- or (S)-hydroxysuccinic acid, respectively, in similar to 9% overall yield. This route enables late stage incorporation of the pyrrole ring at C5 via nucleophilic displacement of an iminium triflate salt. (C) 2013 Elsevier Ltd. All rights reserved.