(-)-(R)-N-(tert-Butoxycarbonyl)-5-n-butyl-2-pyrrolidinone | 160542-13-2

• 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: (-)-(R)-N-(tert-Butoxycarbonyl)-5-n-butyl-2-pyrrolidinone
• 英文别名: tert-butyl (2R)-2-butyl-5-oxopyrrolidine-1-carboxylate
• CAS: 160542-13-2
• 化学式: C₁₃H₂₃NO₃
• 分子量: 241.331
• InChiKey: FYKLOKJGSKIDGA-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(R)-N-(tert-Butoxycarbonyl)-5-n-butyl-2-pyrrolidinone 在 盐酸 、 sodium tetrahydroborate 、 三氟甲磺酸三甲基硅酯 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 34.5h， 生成 (3R,5R,9S)-3-n-Butyl-5-n-propyloctahydroindolizin-7-one (p-toluenesulfonyl)hydrazone
  参考文献：
  名称：

  One-Pot Preparation of Quinolizidin-2-one and Indolizidin-7-one Ring Systems. Concise Total Syntheses of (.+-.)-Myrtine, (.+-.)-Lasubine II, and (-)-Indolizidine 223AB

  摘要：

  highly efficient approach to the quinolizidine alkaloids (+/-)-myrtine (4) and (+/-)-lasubine II (5) and to the indolizidine alkaloid (-)-indolizidine 223AB (6) is described. The preparation of quinolizidin-2-ones 4/4a and 11b/12b and indolizidin-7-ones 16/17 is based on the addition of 2-((trimethylsilyl)oxy) 1,3-dienes 2a,b and 2c to cyclic N-acyliminium ions 10 and 15, respectively. It encompasses five chemical transformations in the same pot yielding the axially oriented substituent at C-4 and C-5 as the major product in the quinolizidin-2-one and indolizidin-7-one systems, respectively. The thermodynamically more stable isomers 12b and 17 were obtained after basic treatment.

  DOI：

  10.1021/jo00108a040
• 作为产物：
  描述：

  (S)-(+)-5-羟甲基-2-吡咯烷酮对甲苯磺酸酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.25h， 生成 (-)-(R)-N-(tert-Butoxycarbonyl)-5-n-butyl-2-pyrrolidinone
  参考文献：
  名称：

  One-Pot Preparation of Quinolizidin-2-one and Indolizidin-7-one Ring Systems. Concise Total Syntheses of (.+-.)-Myrtine, (.+-.)-Lasubine II, and (-)-Indolizidine 223AB

  摘要：

  highly efficient approach to the quinolizidine alkaloids (+/-)-myrtine (4) and (+/-)-lasubine II (5) and to the indolizidine alkaloid (-)-indolizidine 223AB (6) is described. The preparation of quinolizidin-2-ones 4/4a and 11b/12b and indolizidin-7-ones 16/17 is based on the addition of 2-((trimethylsilyl)oxy) 1,3-dienes 2a,b and 2c to cyclic N-acyliminium ions 10 and 15, respectively. It encompasses five chemical transformations in the same pot yielding the axially oriented substituent at C-4 and C-5 as the major product in the quinolizidin-2-one and indolizidin-7-one systems, respectively. The thermodynamically more stable isomers 12b and 17 were obtained after basic treatment.

  DOI：

  10.1021/jo00108a040

文献信息

• Efficient Enantio- and Diastereodivergent Synthesis of Poison-Frog Alkaloids <b>251O</b> and <i>trans</i>-<b>223B</b>
  作者：Naoki Toyooka、Dejun Zhou、Hideo Nemoto、Yasuhiro Tezuka、Shigetoshi Kadota、Nirina R. Andriamaharavo、H. Martin Garraffo、Thomas F. Spande、John W. Daly

  DOI：10.1021/jo901100m

  日期：2009.9.4

  An efficient and flexible synthesis of poison-frog alkaloids 251O and trans-223B has been achieved by using for both alkaloids an enantiodivergent process starting from the common lactam 1. The relative stereochemistry of 251O and trans-223B was determined to be 7 (R = n-C7H15, R' = n-Pr) and 14 by the present enantioselective synthesis.
• One-Pot Preparation of Quinolizidin-2-one and Indolizidin-7-one Ring Systems. Concise Total Syntheses of (.+-.)-Myrtine, (.+-.)-Lasubine II, and (-)-Indolizidine 223AB
  作者：Ronaldo A. Pilli、Luiz Carlos Dias、Adriano O. Maldaner

  DOI：10.1021/jo00108a040

  日期：1995.2

  highly efficient approach to the quinolizidine alkaloids (+/-)-myrtine (4) and (+/-)-lasubine II (5) and to the indolizidine alkaloid (-)-indolizidine 223AB (6) is described. The preparation of quinolizidin-2-ones 4/4a and 11b/12b and indolizidin-7-ones 16/17 is based on the addition of 2-((trimethylsilyl)oxy) 1,3-dienes 2a,b and 2c to cyclic N-acyliminium ions 10 and 15, respectively. It encompasses five chemical transformations in the same pot yielding the axially oriented substituent at C-4 and C-5 as the major product in the quinolizidin-2-one and indolizidin-7-one systems, respectively. The thermodynamically more stable isomers 12b and 17 were obtained after basic treatment.