(+)-(7S,9R)-8-aza-9-methyl-7-n-undecyl-1,4-dithiaspiro[5.4]decane | 288303-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (+)-(7S,9R)-8-aza-9-methyl-7-n-undecyl-1,4-dithiaspiro[5.4]decane
• 英文别名: (7R,9S)-7-methyl-9-undecyl-1,4-dithia-8-azaspiro[4.5]decane；(7S,9R)-9-methyl-7-undecyl-1,4-dithia-8-azaspiro[4.5]decane
• CAS: 288303-22-0
• 化学式: C₁₉H₃₇NS₂
• 分子量: 343.641
• InChiKey: OXQPWCHZBLIQHF-MSOLQXFVSA-N

物化性质

• 沸点：
  453.1±45.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(7S,9R)-8-aza-9-methyl-7-n-undecyl-1,4-dithiaspiro[5.4]decane 在 W₂ Raney-nickel 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以95%的产率得到(+)-isosolenopsin A
  参考文献：
  名称：

  A simple and efficient enantioselective synthesis of piperidine alkaloids dihydropinidine and isosolenopsins A, B and C

  摘要：

  A diastereospecific intramolecular Mannich-type reaction, involving enantiopure amine 4 and achiral aldehydes, is employed as the key step of an efficient total enantioselective synthesis of five piperidine alkaloids. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00162-2
• 作为产物：
  描述：

  (4R)-4-amino-1-trimethylsilyl-2-(trimethylsilylmethyl)pentan-2-ol 在 四氧化锇 、 sodium paraperiodate 、 三氟化硼乙醚 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 42.0h， 生成 (+)-(7S,9R)-8-aza-9-methyl-7-n-undecyl-1,4-dithiaspiro[5.4]decane
  参考文献：
  名称：

  A new asymmetric synthesis of 2,6-cis-disubstituted 4-methylenepiperidines: total synthesis of (+)-alkaloid 241D and (+)-isosolenopsin A

  摘要：

  A highly diastereoselective synthesis of 2,6-cis-disubstituted-4-methylenepiperidines based on a Mannich type intramolecular cyclization of an allylsilane on an iminium ion is described. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of two natural piperidine alkaloids: (+)-alkaloid 241 D and (+)-isosolenopsin A. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.018

文献信息

• A simple and efficient enantioselective synthesis of piperidine alkaloids dihydropinidine and isosolenopsins A, B and C
  作者：Stéphane Ciblat、Pascale Besse、Vassiliki Papastergiou、Henri Veschambre、Jean-Louis Canet、Yves Troin

  DOI：10.1016/s0957-4166(00)00162-2

  日期：2000.6

  A diastereospecific intramolecular Mannich-type reaction, involving enantiopure amine 4 and achiral aldehydes, is employed as the key step of an efficient total enantioselective synthesis of five piperidine alkaloids. (C) 2000 Elsevier Science Ltd. All rights reserved.
• A new asymmetric synthesis of 2,6-cis-disubstituted 4-methylenepiperidines: total synthesis of (+)-alkaloid 241D and (+)-isosolenopsin A
  作者：Jérémy Monfray、Yvonne Gelas-Mialhe、Jean-Claude Gramain、Roland Remuson

  DOI：10.1016/j.tetasy.2005.01.018

  日期：2005.3

  A highly diastereoselective synthesis of 2,6-cis-disubstituted-4-methylenepiperidines based on a Mannich type intramolecular cyclization of an allylsilane on an iminium ion is described. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of two natural piperidine alkaloids: (+)-alkaloid 241 D and (+)-isosolenopsin A. (C) 2005 Elsevier Ltd. All rights reserved.