(E,R)-ethyl 7,8-dihydroxy-oct-2-enoate | 1064038-54-5

• 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: (E,R)-ethyl 7,8-dihydroxy-oct-2-enoate
• 英文别名: ethyl (E,7R)-7,8-dihydroxyoct-2-enoate
• CAS: 1064038-54-5
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: QAXYRVSRYFURFM-VPIOIWJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E,R)-ethyl 7,8-dihydroxy-oct-2-enoate 在 sodium hydride 、 盐酸 作用下， 以 四氢呋喃 、 mineral oil 、 水 为溶剂， 以43%的产率得到(3S,7R)-ethyl 8-hydroxy-3,7-oxido-octanoate
  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：

  (E,R)-ethyl 7,8-(isopropylidenedioxy)-oct-2-enoate 在 水 、 溶剂黄146 作用下， 反应 3.0h， 以91%的产率得到(E,R)-ethyl 7,8-dihydroxy-oct-2-enoate
  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

• Cytotoxin Compounds and Methods of Isolation
  申请人：Baker Bill

  公开号：US20090192215A1

  公开（公告）日：2009-07-30

  The present invention concerns groups of compounds derived from tunicates of the Synoicum species, as well as to pharmaceutical compositions comprising these compounds, and uses thereof. Extracts from tunicates show selective toxicity against several different cancer cell lines in the NCI 60 cell line panel. These compounds are useful in the effective treatment of cancers, particularly malignant melanomas, colon cancer, and renal cancer cell lines.
• Structural Determination of Montanacin D by Total Synthesis
  作者：Shunya Takahashi、Yayoi Hongo、Yuki Tsukagoshi、Hiroyuki Koshino

  DOI：10.1021/ol801576z

  日期：2008.10.2

  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.