methyl (5R)-2-methoxy-5-nonylpyrrolidine-1-carboxylate | 221109-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl (5R)-2-methoxy-5-nonylpyrrolidine-1-carboxylate
• CAS: 221109-86-0
• 化学式: C₁₆H₃₁NO₃
• 分子量: 285.427
• InChiKey: NITWCTQBLNHMMF-GICMACPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (5R)-2-methoxy-5-nonylpyrrolidine-1-carboxylate 在 palladium dihydroxide 三氟甲磺酸三甲基硅酯 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 9.5h， 生成 (2S,3S,5R)-2-(phenylmethyl)-1-carbomethoxy-5-nonyl-3-pyrrolidinol
  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：

  2,2-二甲氧基丙烷 、 (R)-N-Methoxycarbonyl-5-nonyl-2-pyrrolidinone 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以91%的产率得到methyl (5R)-2-methoxy-5-nonylpyrrolidine-1-carboxylate
  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

文献信息

• Unprecedented Facial Diastereoselectivity in the Paternò-Büchi Reaction of a Chiral Dihydropyrrole—A Short Total Synthesis of (+)-Preussin
  作者：Thorsten Bach、Harm Brummerhop

  DOI：10.1002/(sici)1521-3773(19981231)37:24<3400::aid-anie3400>3.0.co;2-3

  日期：1998.12.31
• 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).