2-(3-Butenyl)-6-methyl-2,3,4,5-tetrahydropyridine 1-Oxide | 146174-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(3-Butenyl)-6-methyl-2,3,4,5-tetrahydropyridine 1-Oxide
• 英文别名: 2-but-3-enyl-6-methyl-1-oxido-2,3,4,5-tetrahydropyridin-1-ium
• CAS: 146174-05-2
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: YHTCTQRPHNQMHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3-Butenyl)-6-methyl-2,3,4,5-tetrahydropyridine 1-Oxide 以 甲苯 为溶剂， 反应 20.0h， 以74%的产率得到(1S,4S,8R)-8-Methyl-10-oxa-9-aza-tricyclo[6.2.1.0^4,9]undecane
  参考文献：
  名称：

  Stereoselective synthesis of (.+-.)-indolizidines 167B, 205A, and 207A. Enantioselective synthesis of (-)-indolizidine 209B

  摘要：

  The first syntheses of the dendrobatid indolizidine alkaloids 167B (3), 205A (4), and 207A (5) are described using as a key step the highly stereoselective intramolecular nitrone cycloaddition of the (Z)-N-alkenylnitrone 10 to prepare the isoxazolidine 11. Mesylate-promoted cyclization of the alcohol 12, followed by reductive cleavage of the resulting mesylate salt, afforded the key axial hydroxymethyl compound 13, which was epimerized via the aldehyde to the equatorial alcohol, and was subsequently reduced to the required 8-methyl-substituted indolizidine. The feasibility of extending this strategy to the enantioselective synthesis of such alkaloids was demonstrated in the first synthesis of (-)-indolizidine 209B (6), whose nitrone precursor 10d was obtained from the (S)-glutamate-derived amine 40.

  DOI：

  10.1021/jo00004a012
• 作为产物：
  描述：

  Dec-1-en-9-yn-5-one 在 盐酸 、 盐酸羟胺 、 sodium cyanoborohydride 作用下， 以 吡啶 、 甲醇 、 乙醇 为溶剂， 反应 0.75h， 生成 2-(3-Butenyl)-6-methyl-2,3,4,5-tetrahydropyridine 1-Oxide
  参考文献：
  名称：

  Stereoselective synthesis of (.+-.)-indolizidines 167B, 205A, and 207A. Enantioselective synthesis of (-)-indolizidine 209B

  摘要：

  The first syntheses of the dendrobatid indolizidine alkaloids 167B (3), 205A (4), and 207A (5) are described using as a key step the highly stereoselective intramolecular nitrone cycloaddition of the (Z)-N-alkenylnitrone 10 to prepare the isoxazolidine 11. Mesylate-promoted cyclization of the alcohol 12, followed by reductive cleavage of the resulting mesylate salt, afforded the key axial hydroxymethyl compound 13, which was epimerized via the aldehyde to the equatorial alcohol, and was subsequently reduced to the required 8-methyl-substituted indolizidine. The feasibility of extending this strategy to the enantioselective synthesis of such alkaloids was demonstrated in the first synthesis of (-)-indolizidine 209B (6), whose nitrone precursor 10d was obtained from the (S)-glutamate-derived amine 40.

  DOI：

  10.1021/jo00004a012

文献信息

• N-Alkenyl nitrone dipolar cycloaddition routes to piperidines and indolizidines. Part 8. The scope of tandem reactions involving hydroxylamine-alkyne cyclisations
  作者：Edwin C Davison、Ian T Forbes、Andrew B Holmes、Jacqueline A Warner

  DOI：10.1016/0040-4020(96)00643-6

  日期：1996.8

  A tandem sequence of hydroxylamine-alkyne cyclisation/1,3-dipolar cycloaddition, provides useful entry into tricyclic systems of type 4. The scope of such reactions is explored in this paper. A novel cascade cyclisation of N-hydroxypyrrolidines of type 26 and 28 involving hydroxylamine-alkyne cyclisation, Cope elimination and 1,3-dipolar cycloaddition is also reported.

  羟胺-炔环化/ 1,3-偶极环加成的串联序列，为进入4型三环系统提供了有用的入口。本文探讨了此类反应的范围。还报道了26和28型N-羟基吡咯烷的新型级联环化，包括羟胺-炔环化，Cope消除和1，3-偶极环加成。
• Hydroxylamine-alkyne cyclisations. A new method for the synthesis of cyclic nitrones
  作者：Martin E. Fox、Andrew B. Holmes、Ian T. Forbes、Mervyn Thompson

  DOI：10.1016/s0040-4039(00)60205-8

  日期：1992.11

  The intramolecular cyclisation of the alkynylhydroxylamines 2, 5a, 8, 11, 16 and 19 provides the cyclic nitrones 3, 9, 12, 17 and 20 in good yields.

  所述alkynylhydroxylamines的分子内环化2，图5a，8，11，16和19提供了环状硝酮3，9，12，17和20以良好的收率。
• Fox, Martin E.; Holmes, Andrew B.; Forbes, Ian T., Journal of the Chemical Society. Perkin transactions I, 1994, # 23, p. 3379 - 3396
  作者：Fox, Martin E.、Holmes, Andrew B.、Forbes, Ian T.、Thompson, Mervyn

  DOI：——

  日期：——
• HOLMES, ANDREW B.;SMITH, ADRIAN L.;WILLIAMS, SIMON F.;HUGHES, LESLIE R.;L+, J. ORG. CHEM., 56,(1991) N, C. 1395-1405
  作者：HOLMES, ANDREW B.、SMITH, ADRIAN L.、WILLIAMS, SIMON F.、HUGHES, LESLIE R.、L+

  DOI：——

  日期：——
• Stereoselective synthesis of (.+-.)-indolizidines 167B, 205A, and 207A. Enantioselective synthesis of (-)-indolizidine 209B
  作者：Andrew B. Holmes、Adrian L. Smith、Simon F. Williams、Leslie R. Hughes、Zev Lidert、Colin Swithenbank

  DOI：10.1021/jo00004a012

  日期：1991.2

  The first syntheses of the dendrobatid indolizidine alkaloids 167B (3), 205A (4), and 207A (5) are described using as a key step the highly stereoselective intramolecular nitrone cycloaddition of the (Z)-N-alkenylnitrone 10 to prepare the isoxazolidine 11. Mesylate-promoted cyclization of the alcohol 12, followed by reductive cleavage of the resulting mesylate salt, afforded the key axial hydroxymethyl compound 13, which was epimerized via the aldehyde to the equatorial alcohol, and was subsequently reduced to the required 8-methyl-substituted indolizidine. The feasibility of extending this strategy to the enantioselective synthesis of such alkaloids was demonstrated in the first synthesis of (-)-indolizidine 209B (6), whose nitrone precursor 10d was obtained from the (S)-glutamate-derived amine 40.