2-[(4S,5R)-5-[(E)-2-(benzenesulfonyl)ethenoxy]-2-phenyl-1,3-dioxan-4-yl]acetaldehyde | 1147012-55-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(4S,5R)-5-[(E)-2-(benzenesulfonyl)ethenoxy]-2-phenyl-1,3-dioxan-4-yl]acetaldehyde
• CAS: 1147012-55-2
• 化学式: C₂₀H₂₀O₆S
• 分子量: 388.441
• InChiKey: OXYXFSZAGKBKEZ-DXRFLOGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(4S,5R)-5-[(E)-2-(benzenesulfonyl)ethenoxy]-2-phenyl-1,3-dioxan-4-yl]acetaldehyde 在 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到
  参考文献：
  名称：

  Synthesis of 2-Methylenetetrahydropyran-3-ol Derivative, a Key Segment for Convergent Synthesis of Polycyclic Ethers Based on Suzuki-Miyaura Coupling

  摘要：

  2-Methylenetetrahydropyran-3-ol derivative, a key segment for convergent synthesis of polycyclic ethers based on Suzuki-Miyaura coupling, was efficiently synthesized by two methods; (1) via SmI2-induced reductive cyclization of beta-alkoxyvinyl sulfone with aldehyde followed by elimination of the sulforyl group, and (2) via SmI2-induced cyclization of beta-alkoxyvinyl sulfoxide with aldehyde followed by dehydration of the 2-hydroxymethyl group.

  DOI：

  10.3987/com-08-s(f)100
• 作为产物：
  描述：

  (4S,5R)-4-((1,3-dithian-2-yl)methyl)-2-phenyl-5-(((E)-2-(phenylsulfonyl)vinyl)oxy)-1,3-dioxane 在 calcium carbonate 、 碘甲烷 作用下， 以 水 、 乙腈 为溶剂， 生成 2-[(4S,5R)-5-[(E)-2-(benzenesulfonyl)ethenoxy]-2-phenyl-1,3-dioxan-4-yl]acetaldehyde
  参考文献：
  名称：

  Synthesis of 2-Methylenetetrahydropyran-3-ol Derivative, a Key Segment for Convergent Synthesis of Polycyclic Ethers Based on Suzuki-Miyaura Coupling

  摘要：

  2-Methylenetetrahydropyran-3-ol derivative, a key segment for convergent synthesis of polycyclic ethers based on Suzuki-Miyaura coupling, was efficiently synthesized by two methods; (1) via SmI2-induced reductive cyclization of beta-alkoxyvinyl sulfone with aldehyde followed by elimination of the sulforyl group, and (2) via SmI2-induced cyclization of beta-alkoxyvinyl sulfoxide with aldehyde followed by dehydration of the 2-hydroxymethyl group.

  DOI：

  10.3987/com-08-s(f)100

文献信息

• Synthesis of 2-Methylenetetrahydropyran-3-ol Derivative, a Key Segment for Convergent Synthesis of Polycyclic Ethers Based on Suzuki-Miyaura Coupling
  作者：Tadashi Nakata、Tomohiro Kimura、Yasuyo Miyagawa、Shingo Ozawa、Mayumi Hagiwara

  DOI：10.3987/com-08-s(f)100

  日期：——

  2-Methylenetetrahydropyran-3-ol derivative, a key segment for convergent synthesis of polycyclic ethers based on Suzuki-Miyaura coupling, was efficiently synthesized by two methods; (1) via SmI2-induced reductive cyclization of beta-alkoxyvinyl sulfone with aldehyde followed by elimination of the sulforyl group, and (2) via SmI2-induced cyclization of beta-alkoxyvinyl sulfoxide with aldehyde followed by dehydration of the 2-hydroxymethyl group.