1-(2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl)but-2-yn-1-ol | 1252660-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl)but-2-yn-1-ol
• 英文别名: (1R)-1-[(2R,4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl]but-2-yn-1-ol
• CAS: 1252660-35-7
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: DYLHEPOMTJNGOO-OWCLPIDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl)but-2-yn-1-ol 在 potassium hydride 、 1,3-丙二胺 作用下， 反应 10.0h， 以91%的产率得到(R)-1-((2R,4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl)but-3-yn-1-ol
  参考文献：
  名称：

  Stereocontrol of 5,5-Spiroketals in the Synthesis of Cephalosporolide H Epimers

  摘要：

  A blueprint for controlling the stereochemistry of oxygenated 5,5-spiroketals using chelation effects is provided. Chelation specifically of zinc salts (other protic and Lewis acids were less effective) between the spiroketal oxygen and an appropriately positioned alcohol group overrides normal biases in the preparation of 5,5-spiroketals, as illustrated by the stereocontrolled synthesis of epimeric cephalosporolide H isomers. This study provides new and valuable information for prescribing the chirality of the stereogenic core of 5,5-spiroketals.

  DOI：

  10.1021/ol102201z
• 作为产物：
  描述：

  1-((2R,4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl)but-2-yn-1-one 在 borane-dimethyl sulfide complex 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以558 mg的产率得到1-(2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl)but-2-yn-1-ol
  参考文献：
  名称：

  Stereocontrol of 5,5-Spiroketals in the Synthesis of Cephalosporolide H Epimers

  摘要：

  A blueprint for controlling the stereochemistry of oxygenated 5,5-spiroketals using chelation effects is provided. Chelation specifically of zinc salts (other protic and Lewis acids were less effective) between the spiroketal oxygen and an appropriately positioned alcohol group overrides normal biases in the preparation of 5,5-spiroketals, as illustrated by the stereocontrolled synthesis of epimeric cephalosporolide H isomers. This study provides new and valuable information for prescribing the chirality of the stereogenic core of 5,5-spiroketals.

  DOI：

  10.1021/ol102201z

文献信息

• A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis
  作者：Sami Tlais、Ronald Clark、Gregory Dudley

  DOI：10.3390/molecules14125216

  日期：——

  four-step, asymmetric synthesis of a chiral propargyl alcohol 1 from (R)-pantolactone is described. A key feature of the synthesis is a diastereoselective acetylide addition to a chiral alpha-alkoxy-aldehyde 7, in which unusual Felkin selectivity is observed, despite the potential for chelation control. Crystalline propargyl alcohol 1 is valuable for complex molecule synthesis, and is easy to prepare

  描述了从 (R)-泛内酯合成手性炔丙醇 1 的四步不对称合成。该合成的一个关键特征是非对映选择性乙炔化物添加到手性 α-烷氧基醛 7 中，尽管具有螯合控制的潜力，但仍观察到了不寻常的 Felkin 选择性。结晶炔丙醇 1 对于复杂分子的合成很有价值，并且易于制备多克数量和高非对映体纯度。
• Stereocontrol of 5,5-Spiroketals in the Synthesis of Cephalosporolide H Epimers
  作者：Sami F. Tlais、Gregory B. Dudley

  DOI：10.1021/ol102201z

  日期：2010.10.15

  A blueprint for controlling the stereochemistry of oxygenated 5,5-spiroketals using chelation effects is provided. Chelation specifically of zinc salts (other protic and Lewis acids were less effective) between the spiroketal oxygen and an appropriately positioned alcohol group overrides normal biases in the preparation of 5,5-spiroketals, as illustrated by the stereocontrolled synthesis of epimeric cephalosporolide H isomers. This study provides new and valuable information for prescribing the chirality of the stereogenic core of 5,5-spiroketals.