(S)-2-Ethynyl-4-methyl-3,6-dihydro-2H-pyran | 688743-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (S)-2-Ethynyl-4-methyl-3,6-dihydro-2H-pyran
• 英文别名: (2S)-2-ethynyl-4-methyl-3,6-dihydro-2H-pyran
• CAS: 688743-61-5
• 化学式: C₈H₁₀O
• 分子量: 122.167
• InChiKey: JOACGSZKEPMMMG-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-2-Ethynyl-4-methyl-3,6-dihydro-2H-pyran 在 Schwartz's reagent 、 碘 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到(2S)-2-[(E)-2-iodovinyl]-4-methyl-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  Synthesis of Novel 11-Desmethyl Analogues of Laulimalide by Nozaki−Kishi Coupling

  摘要：

  As a first entry into structurally simplified analogues of the anticancer agent laulimalide, 11-desmethyl compounds 2 and 3 were selected by molecular modeling. The unfavorable diastereoselectivity in the key synthetic step, a Nozaki-Kishi coupling between macrocyclic aldehyde 4 and vinyl iodide 5, was overcome either by use of catalytic amounts of DIANANE-type ligands or L-Selectride reduction of the derived enone. This methodology should allow modular introduction of other, unnatural, side chains.

  DOI：

  10.1021/ol049791q
• 作为产物：
  描述：

  (1-重氮基-2-氧代丙基)膦酸二甲酯 、 (2S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (S)-2-Ethynyl-4-methyl-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  Synthesis of Novel 11-Desmethyl Analogues of Laulimalide by Nozaki−Kishi Coupling

  摘要：

  As a first entry into structurally simplified analogues of the anticancer agent laulimalide, 11-desmethyl compounds 2 and 3 were selected by molecular modeling. The unfavorable diastereoselectivity in the key synthetic step, a Nozaki-Kishi coupling between macrocyclic aldehyde 4 and vinyl iodide 5, was overcome either by use of catalytic amounts of DIANANE-type ligands or L-Selectride reduction of the derived enone. This methodology should allow modular introduction of other, unnatural, side chains.

  DOI：

  10.1021/ol049791q

文献信息

• Synthesis of Novel 11-Desmethyl Analogues of Laulimalide by Nozaki−Kishi Coupling
  作者：Ian Paterson、Hermann Bergmann、Dirk Menche、Albrecht Berkessel

  DOI：10.1021/ol049791q

  日期：2004.4.1

  As a first entry into structurally simplified analogues of the anticancer agent laulimalide, 11-desmethyl compounds 2 and 3 were selected by molecular modeling. The unfavorable diastereoselectivity in the key synthetic step, a Nozaki-Kishi coupling between macrocyclic aldehyde 4 and vinyl iodide 5, was overcome either by use of catalytic amounts of DIANANE-type ligands or L-Selectride reduction of the derived enone. This methodology should allow modular introduction of other, unnatural, side chains.