2-((tetrahydrofuran-2-yl)methyl)-2-(4-methylpenta-2,3-dienyl)-malonic acid dimethyl ester | 1303559-39-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-((tetrahydrofuran-2-yl)methyl)-2-(4-methylpenta-2,3-dienyl)-malonic acid dimethyl ester
• CAS: 1303559-39-8
• 化学式: C₁₆H₂₄O₅
• 分子量: 296.364
• InChiKey: NBOACKZNWRQKGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((tetrahydrofuran-2-yl)methyl)-2-(4-methylpenta-2,3-dienyl)-malonic acid dimethyl ester 在 双三氟甲烷磺酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以95%的产率得到rac-(5S,10S)-10-Isopropenyl-1-oxa-spiro[4.5]decane-7,7-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Gold and Brønsted Acid Catalyzed Hydride Shift onto Allenes: Divergence in Product Selectivity

  摘要：

  A series of allenyl ethers can be transformed into various fused or spiro tetrahydrofurans and tetrahydropyrans following a hydride shift/cyclization sequence. A divergence in product selectivity, which depends on the nature of the catalyst used (Au(I) complex or Bronsted acid), was observed.

  DOI：

  10.1021/ja202336p
• 作为产物：
  描述：

  dimethyl 2-((tetrahydrofuran-2-yl)methyl)malonate 、 4-methyl-2,3-pentadienyl methanesulfonate 在 sodium hydride 、 四丁基碘化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以56%的产率得到2-((tetrahydrofuran-2-yl)methyl)-2-(4-methylpenta-2,3-dienyl)-malonic acid dimethyl ester
  参考文献：
  名称：

  Gold and Brønsted Acid Catalyzed Hydride Shift onto Allenes: Divergence in Product Selectivity

  摘要：

  A series of allenyl ethers can be transformed into various fused or spiro tetrahydrofurans and tetrahydropyrans following a hydride shift/cyclization sequence. A divergence in product selectivity, which depends on the nature of the catalyst used (Au(I) complex or Bronsted acid), was observed.

  DOI：

  10.1021/ja202336p

文献信息

• Gold and Brønsted Acid Catalyzed Hydride Shift onto Allenes: Divergence in Product Selectivity
  作者：Benoit Bolte、Fabien Gagosz

  DOI：10.1021/ja202336p

  日期：2011.5.25

  A series of allenyl ethers can be transformed into various fused or spiro tetrahydrofurans and tetrahydropyrans following a hydride shift/cyclization sequence. A divergence in product selectivity, which depends on the nature of the catalyst used (Au(I) complex or Bronsted acid), was observed.