(-)-(3R,5R,9S)-3-n-Butyl-5-n-propyloctahydroindolizin-7-one | 160637-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (-)-(3R,5R,9S)-3-n-Butyl-5-n-propyloctahydroindolizin-7-one
• 英文别名: (3R,5R,8aS)-3-butyl-5-propyl-2,3,5,6,8,8a-hexahydro-1H-indolizin-7-one
• CAS: 160637-23-0
• 化学式: C₁₅H₂₇NO
• 分子量: 237.385
• InChiKey: ZMGNRKJKPIFROD-MCIONIFRSA-N

物化性质

• 沸点：
  340.8±17.0 °C(predicted)
• 密度：
  0.97±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(3R,5R,9S)-3-n-Butyl-5-n-propyloctahydroindolizin-7-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 8.5h， 生成 (3R*,5R*,8aR*)-3-Butyl-5-propyloctahydroindolizine (GTX 223AB)
  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 盐酸 、 sodium tetrahydroborate 、 三氟甲磺酸三甲基硅酯 、 碳酸氢钠 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 35.75h， 生成 (-)-(3R,5R,9S)-3-n-Butyl-5-n-propyloctahydroindolizin-7-one
  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

• Rearrangement of isoxazoline-5-spiro derivatives. 5. Diastereofacial selectivity in the cycloaddition of substituted five-membered cyclic nitrones and methylenecyclopropanes. Stereoselective synthesis of 3,5-substituted indolizidinones
  作者：Franca M. Cordero、Alberto Brandi、Cecilia Querci、Andrea Goti、Francesco De Sarlo、Antonio Guarna

  DOI：10.1021/jo00293a018

  日期：1990.3
• CORDERO, FRANCA M.;BRANDI, ALBERTO;QUERCI, CECILIA;GOTI, ANDREA;DE, SARLO+, J. ORG. CHEM., 55,(1990) N, C. 1762-1767
  作者：CORDERO, FRANCA M.、BRANDI, ALBERTO、QUERCI, CECILIA、GOTI, ANDREA、DE, SARLO+

  DOI：——

  日期：——
• 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.