(1R,5R)-6-(4-methoxybenzyl)-2-oxa-6-azabicyclo[3.3.0]octan-3,7-dione | 812644-96-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡咯
• 英文名称: (1R,5R)-6-(4-methoxybenzyl)-2-oxa-6-azabicyclo[3.3.0]octan-3,7-dione
• 英文别名: (3aR,6aR)-Tetrahydro-4-[(4-methoxyphenyl)methyl]-2H-furo[3,2-b]pyrrole-2,5(3H)-dione；(3aR,6aR)-4-[(4-methoxyphenyl)methyl]-3,3a,6,6a-tetrahydrofuro[3,2-b]pyrrole-2,5-dione
• CAS: 812644-96-5
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: LAPUOERCYFQYGB-VXGBXAGGSA-N

物化性质

• 熔点：
  109-111 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  533.2±50.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿；二氯甲烷；甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,5R)-6-(4-methoxybenzyl)-2-oxa-6-azabicyclo[3.3.0]octan-3,7-dione 在 palladium on activated charcoal 盐酸 、 dimethyl sulfide borane 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 19.5h， 生成 (+)-(1R,5R)-2-oxa-6-azabicyclo[3.3.0]octan-3-one hydrochloride
  参考文献：
  名称：

  A novel approach to the Geissman–Waiss lactone and a key intermediate in the synthesis of pyrrolidine trans-lactones

  摘要：

  Based on the highly regio- and diastereoselective reductive-ethoxycarbonylmethylation of protected (S)-malimide 4, a new approach to the Geissman-Waiss lactone 1 and a key intermediate 3 for the synthesis of pyrrolidine trans-lactones (e.g., 2) is described. The synthesis features a one-step and a two-step chemoselective reduction of an amide carbonyl in the presence of an ester group as the key steps. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.020
• 作为产物：
  描述：

  [(S)-3-Benzyloxy-2-hydroxy-1-(4-methoxy-benzyl)-5-oxo-pyrrolidin-2-yl]-acetic acid ethyl ester 在 palladium on activated charcoal 三乙基硅烷 、 lithium hydroxide 、 三氟化硼乙醚 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 221.5h， 生成 (1R,5R)-6-(4-methoxybenzyl)-2-oxa-6-azabicyclo[3.3.0]octan-3,7-dione
  参考文献：
  名称：

  A novel approach to the Geissman–Waiss lactone and a key intermediate in the synthesis of pyrrolidine trans-lactones

  摘要：

  Based on the highly regio- and diastereoselective reductive-ethoxycarbonylmethylation of protected (S)-malimide 4, a new approach to the Geissman-Waiss lactone 1 and a key intermediate 3 for the synthesis of pyrrolidine trans-lactones (e.g., 2) is described. The synthesis features a one-step and a two-step chemoselective reduction of an amide carbonyl in the presence of an ester group as the key steps. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.020

文献信息

• A novel approach to the Geissman–Waiss lactone and a key intermediate in the synthesis of pyrrolidine trans-lactones
  作者：Jing-Xing Du、Hui-Ying Huang、Pei-Qiang Huang

  DOI：10.1016/j.tetasy.2004.09.020

  日期：2004.11

  Based on the highly regio- and diastereoselective reductive-ethoxycarbonylmethylation of protected (S)-malimide 4, a new approach to the Geissman-Waiss lactone 1 and a key intermediate 3 for the synthesis of pyrrolidine trans-lactones (e.g., 2) is described. The synthesis features a one-step and a two-step chemoselective reduction of an amide carbonyl in the presence of an ester group as the key steps. (C) 2004 Elsevier Ltd. All rights reserved.