(2S,6S)-2-methyl-6-nonylpiperidine | 1450977-34-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (2S,6S)-2-methyl-6-nonylpiperidine
• 英文别名: trans-2-Methyl-6-nonylpiperidine
• CAS: 1450977-34-0
• 化学式: C₁₅H₃₁N
• 分子量: 225.418
• InChiKey: REJJGCFUHWQZBH-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S,6S)-2-methyl-6-nonylpiperidine 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (+)-solenopsin hydrochloride
  参考文献：
  名称：

  Enantioselective Synthesis of cis- and trans-2-Methyl-6-nonylpiperidines: Alkaloids Solenopsin and Isosolenopsin

  摘要：

  The cross-metathesis of the enantioenriched homoallylic amine 8 (readily accessible by alpha-aminoallylation of decanal) with methyl vinyl ketone using the Hoveyda-Blechert catalyst 10 in presence of 10 mol% of Ti(O-i-Pr)(4) led exclusively to the (E)-enone 11, which by stereoselective reductive amination affords (+)-isosolenopsin (3a) and (+)-solenopsin (4a) with excellent selectivities.

  DOI：

  10.3987/com-12-s(n)27
• 作为产物：
  描述：

  (4S,S_S)-N-(tert-butanesulfinyl)tridec-1-en-4-amine 在 titanium(IV) isopropylate 、 盐酸 、 Wilkinson's catalyst 、 Hoveyda-Grubbs catalyst second generation 、 氢气 、 三甲基铝 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 正庚烷 、 二氯甲烷 为溶剂， -78.0~45.0 ℃ 、101.33 kPa 条件下， 反应 43.17h， 生成 (2S,6S)-2-methyl-6-nonylpiperidine 、 (+)-solenopsin hydrochloride
  参考文献：
  名称：

  Enantioselective Synthesis of cis- and trans-2-Methyl-6-nonylpiperidines: Alkaloids Solenopsin and Isosolenopsin

  摘要：

  The cross-metathesis of the enantioenriched homoallylic amine 8 (readily accessible by alpha-aminoallylation of decanal) with methyl vinyl ketone using the Hoveyda-Blechert catalyst 10 in presence of 10 mol% of Ti(O-i-Pr)(4) led exclusively to the (E)-enone 11, which by stereoselective reductive amination affords (+)-isosolenopsin (3a) and (+)-solenopsin (4a) with excellent selectivities.

  DOI：

  10.3987/com-12-s(n)27

文献信息

• Total Synthesis of Pyrrolidine and Piperidine Natural Products via TMSOTf-Mediated “5/6-<i>endo-dig</i>” Reductive Hydroamination of Enynyl Amines
  作者：Santosh J. Gharpure、Raj K. Patel、Krishna S. Gupta

  DOI：10.1021/acs.orglett.3c02115

  日期：2023.8.11

  acid-mediated 5/6-endo-dig reductive hydroamination cascade of enynyl amines. The brevity of the developed strategy allowed for the collective stereoselective total synthesis of various alkaloids, including (±)-pyrrolidine cis-225H, (±)-epi-197B, (±)-epi-225C, the family of (+)-solenopsins and (+)-isosolenopsins, and the formal synthesis of (±)-bgugaine and (+)-azimic acid.

  带有疏水链的吡咯烷和哌啶的立体选择性合成已经通过烯炔胺的无金属、路易斯酸介导的5/6-内位还原氢胺化级联实现。所开发策略的简洁性允许集体立体选择性全合成各种生物碱，包括(±)-吡咯烷顺式-225H、(±)- epi -197B、(±)- epi -225C、(+)-家族Solenopins 和 (+)-isosolenopsins，以及 (±)-bgugaine 和 (+)-azimic Acid 的正式合成。
• Enantioselective Synthesis of cis- and trans-2-Methyl-6-nonylpiperidines: Alkaloids Solenopsin and Isosolenopsin
  作者：Miguel Yus、José Carlos González-Gómez、Mohamed Medjahdi、Francisco Foubelo

  DOI：10.3987/com-12-s(n)27

  日期：——

  The cross-metathesis of the enantioenriched homoallylic amine 8 (readily accessible by alpha-aminoallylation of decanal) with methyl vinyl ketone using the Hoveyda-Blechert catalyst 10 in presence of 10 mol% of Ti(O-i-Pr)(4) led exclusively to the (E)-enone 11, which by stereoselective reductive amination affords (+)-isosolenopsin (3a) and (+)-solenopsin (4a) with excellent selectivities.