6-allyl-3-methyltetrahydropyran-2-one | 219779-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 6-allyl-3-methyltetrahydropyran-2-one
• 英文别名: 3-Methyl-6-prop-2-enyloxan-2-one
• CAS: 219779-32-5
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: HWOFFIOFQFEERI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-allyl-3-methyltetrahydropyran-2-one 在 LiN(SiMe)3 、 camphor-10-sulfonic acid 、 臭氧 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 (4R)-4-[3-hydroxy-4-[(2R,3R,7R,10S)-2,3,10-trimethyl-1,4,6-trioxaspiro[4.5]decan-7-yl]butanoyl]-3-[(4-methoxyphenyl)methyl]-1,3-thiazolidin-2-one
  参考文献：
  名称：

  （+）-latrunculin B的全合成。

  摘要：

  DOI：

  10.1021/ja00269a056
• 作为产物：
  描述：

  5-Hydroxy-2-methyl-oct-7-enoic acid 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 6-allyl-3-methyltetrahydropyran-2-one
  参考文献：
  名称：

  Total Synthesis of (±)-Quinolizidine 217A

  摘要：

  Several 1,4-disubstituted quinolizidines have been isolated in minute quantities from the skin of certain poisonous frogs and toads. The structures of these alkaloids have been proposed mainly on the basis of MS and IR spectroscopic data. We report the first total synthesis of a naturally occurring alkaloid of this type, quinolizidine 217A. After examination of several azide-based routes, the cyclization of an azide onto an ester-bearing alkene provided a 3,4,5,6-tetrahydropyridine that was reduced in a stereoselective fashion to produce a cis-2,6-disubstituted piperidine (25 --> 31 --> 32). Transformation of 32 into quinolizidine 217A (2) and its C(1) epimer (41) were accomplished in a straightforward fashion. Synthetic quinolizidine 217A was found to be identical to the natural alkaloid, confirming its stereostructure. Compound 41 has the same stereostructure as that proposed for the alkaloid quinolizidine 207I, a compound whose configuration was recently revised as a result of synthetic studies by Momose et al., who synthesized a 1,4-disubstituted quinolizidine with the configuration previously proposed for quinolizidine 207I and found the synthetic material to be epimeric with the natural material. Compound 41 should provide a useful point of comparison for future studies on the stereostructure of natural or synthetic quinolizidine 207I.

  DOI：

  10.1021/jo981695d

文献信息

• Total synthesis of the latrunculins
  作者：Amos B. Smith、James W. Leahy、Ichio Noda、Stacy W. Remiszewski、Nigel J. Liverton、Regina Zibuck

  DOI：10.1021/ja00034a036

  日期：1992.4

  syntheses of (+)-latrunculin A (1) and (+)-latrunculin B (2), two architecturally novel toxins isolated from the Red Sea sponge Latrunculia magnifica (Keller), have been achieved via highly convergent and stereocontrolled routes (longest linear sequences, 16 and 12 steps, respectively). Formal syntheses of scalemic latrunculins C (3) and M (5) also derive from the construction of 2. Central features of the

  (+)-latrunculin A (1) 和 (+)-latrunculin B (2) 的全合成是从红海海绵 Latrunculia magnifica (Keller) 中分离出的两种结构新颖的毒素，已通过高度收敛和立体控制的路线实现。最长的线性序列，分别为 16 和 12 步）。scalemic latrunculins C (3) 和 M (5) 的正式合成也来源于 2 的构建。统一合成策略的核心特征包括醛 (-)-12 与甲基酮 (-)-13 的羟醛反应，a原酸酯 (-)-11 的新型酸催化重组平衡和大环内光信封环化
• Milne, Jacqueline E.; Kocienski, Philip J., Synthesis, 2003, # 4, p. 584 - 592
  作者：Milne, Jacqueline E.、Kocienski, Philip J.

  DOI：——

  日期：——
• Total synthesis of (+)-latrunculin B
  作者：Regina. Zibuck、Nigel J. Liverton、Amos B. Smith

  DOI：10.1021/ja00269a056

  日期：1986.4
• Total Synthesis of (±)-Quinolizidine 217A
  作者：William H. Pearson、Hiroyuki Suga

  DOI：10.1021/jo981695d

  日期：1998.12.1

  Several 1,4-disubstituted quinolizidines have been isolated in minute quantities from the skin of certain poisonous frogs and toads. The structures of these alkaloids have been proposed mainly on the basis of MS and IR spectroscopic data. We report the first total synthesis of a naturally occurring alkaloid of this type, quinolizidine 217A. After examination of several azide-based routes, the cyclization of an azide onto an ester-bearing alkene provided a 3,4,5,6-tetrahydropyridine that was reduced in a stereoselective fashion to produce a cis-2,6-disubstituted piperidine (25 --> 31 --> 32). Transformation of 32 into quinolizidine 217A (2) and its C(1) epimer (41) were accomplished in a straightforward fashion. Synthetic quinolizidine 217A was found to be identical to the natural alkaloid, confirming its stereostructure. Compound 41 has the same stereostructure as that proposed for the alkaloid quinolizidine 207I, a compound whose configuration was recently revised as a result of synthetic studies by Momose et al., who synthesized a 1,4-disubstituted quinolizidine with the configuration previously proposed for quinolizidine 207I and found the synthetic material to be epimeric with the natural material. Compound 41 should provide a useful point of comparison for future studies on the stereostructure of natural or synthetic quinolizidine 207I.