(R)-N-methoxycarbonyl-2-ethyl-2,3-dihydropyrrole | 226991-23-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (R)-N-methoxycarbonyl-2-ethyl-2,3-dihydropyrrole
• 英文别名: methyl (2R)-2-ethyl-2,3-dihydropyrrole-1-carboxylate
• CAS: 226991-23-7
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: XPPAMJKIWAJLBG-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 (R)-N-methoxycarbonyl-2-ethyl-2,3-dihydropyrrole 以 乙腈 为溶剂， 反应 5.0h， 生成 (1R,3R,5S,7R)-3-Ethyl-7-phenyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester 、 (1S,3R,5R,7S)-3-Ethyl-7-phenyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  The Synthesis of (+)-Preussin and Related Pyrrolidinols by Diastereoselective Paternò-Büchi Reactions of Chiral 2-Substituted 2,3-Dihydropyrroles

  摘要：

  The N-alkoxycarbonyl substituted 2,3-dihydropyrroles 3 and 8 are converted to 2-benzyl-3-pyrrolidinols by the Paterno-Buchi reaction followed by hydrogenolysis. Since the addition of the photoexcited benzaldehyde at the unsaturated heterocycle proceeds in a syn fashion, the benzyl group at C-2 and the hydroxy group at C-3 of the product are cis oriented. The simple and facial diastereoselectivities of the Paterno-Buchi reaction were studied more closely and the relative configuration of the products was elucidated. The thermodynamically less stable endo product is formed as a result of simple diastereoselection. The face differentiation in 2-substituted 2,3-dihydropyrroles is presumably due to the nonplanarity of these heterocycles, which forces attack of the carbonyl group on the face with the existing substituent. All-cis-pyrrolidinols are consequently formed after hydrogenolysis. Following this route, a total synthesis of the pyrrolidinol alkaloid (+)-preussin (1) was conducted, which yielded the target compound in a total yield of 11% over nine steps starting from L-pyroglutaminol (11).

  DOI：

  10.1002/1521-3765(20001016)6:20<3838::aid-chem3838>3.0.co;2-1
• 作为产物：
  描述：

  (2RS,5R)-N-methoxycarbonyl-5-ethyl-2-methoxypyrrolidine 在 三氟甲磺酸三甲基硅酯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以79%的产率得到(R)-N-methoxycarbonyl-2-ethyl-2,3-dihydropyrrole
  参考文献：
  名称：

  Bach, Thorsten; Brummerhop, Harm, Advanced Synthesis and Catalysis, 1999, vol. 341, # 3, p. 312 - 315

  摘要：

  DOI：

文献信息

• Bach, Thorsten; Brummerhop, Harm, Advanced Synthesis and Catalysis, 1999, vol. 341, # 3, p. 312 - 315
  作者：Bach, Thorsten、Brummerhop, Harm

  DOI：——

  日期：——
• The Synthesis of (+)-Preussin and Related Pyrrolidinols by Diastereoselective Paternò-Büchi Reactions of Chiral 2-Substituted 2,3-Dihydropyrroles
  作者：Thorsten Bach、Harm Brummerhop、Klaus Harms

  DOI：10.1002/1521-3765(20001016)6:20<3838::aid-chem3838>3.0.co;2-1

  日期：2000.10.16

  The N-alkoxycarbonyl substituted 2,3-dihydropyrroles 3 and 8 are converted to 2-benzyl-3-pyrrolidinols by the Paterno-Buchi reaction followed by hydrogenolysis. Since the addition of the photoexcited benzaldehyde at the unsaturated heterocycle proceeds in a syn fashion, the benzyl group at C-2 and the hydroxy group at C-3 of the product are cis oriented. The simple and facial diastereoselectivities of the Paterno-Buchi reaction were studied more closely and the relative configuration of the products was elucidated. The thermodynamically less stable endo product is formed as a result of simple diastereoselection. The face differentiation in 2-substituted 2,3-dihydropyrroles is presumably due to the nonplanarity of these heterocycles, which forces attack of the carbonyl group on the face with the existing substituent. All-cis-pyrrolidinols are consequently formed after hydrogenolysis. Following this route, a total synthesis of the pyrrolidinol alkaloid (+)-preussin (1) was conducted, which yielded the target compound in a total yield of 11% over nine steps starting from L-pyroglutaminol (11).