(R)-2,2-dimethyl-4-(pent-4-enyl)-1,3-dioxolane | 1064038-47-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2,2-dimethyl-4-(pent-4-enyl)-1,3-dioxolane
• CAS: 1064038-47-6
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: WZSWEZIXIFYNRC-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-2,2-dimethyl-4-(pent-4-enyl)-1,3-dioxolane 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]butanal
  参考文献：
  名称：

  Structural Determination of Montanacin D by Total Synthesis

  摘要：

  The first total syntheses of acetogenin 3 and its 4S,8R-isomer are described. The key step involves intermolecular metathesis of an alpha,beta-unsaturated ketone carrying a tetra hydropyranyl lactone with a tetrahydrofuran derivative. Compound 3 has spectroscopic and physical data consistent with those of natural montanacin D, suggesting that the absolute configuration of the natural product is as shown in 3.

  DOI：

  10.1021/ol801576z
• 作为产物：
  描述：

  氯丙烯镁 、 (4R)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 23.5h， 以73%的产率得到(R)-2,2-dimethyl-4-(pent-4-enyl)-1,3-dioxolane
  参考文献：
  名称：

  Structural Determination of Montanacin D by Total Synthesis

  摘要：

  The first total syntheses of acetogenin 3 and its 4S,8R-isomer are described. The key step involves intermolecular metathesis of an alpha,beta-unsaturated ketone carrying a tetra hydropyranyl lactone with a tetrahydrofuran derivative. Compound 3 has spectroscopic and physical data consistent with those of natural montanacin D, suggesting that the absolute configuration of the natural product is as shown in 3.

  DOI：

  10.1021/ol801576z

文献信息

• Total Synthesis of (+)-Goniodenin
  作者：Tsuyoshi Ueda、Ai Suzuki、Mai Sasaki、Naoyuki Hoshiya、Jun’ichi Uenishi

  DOI：10.1021/acs.joc.6b02432

  日期：2016.12.16

  Goniodenin is a lipophilic polyketide originating from plant sources and which possesses a potent cytotoxic activity against cancer cell lines. The first total synthesis of (+)-goniodenin has been achieved in 23 steps from (R)-glycidol. The synthetic sequence featured a cross metathesis for the formation of the C-8-C-9 bond and installation of the terminal gamma-butenolactone ring unit by the allcylation of alpha-phenylthio-gamma-butyrolactone with the corresponding C-3-O-triflate. The stereogenic center at C-18 carbon was created by Hiyama Fujita reduction of the corresponding ketone with high diastereoselectivity.