ethyl (2E,5S)-6-[(4R)-2,2-dimethyl-1,3-dioxan-4-yl]-5-methylhex-2-enoate | 1580449-14-4

• 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: ethyl (2E,5S)-6-[(4R)-2,2-dimethyl-1,3-dioxan-4-yl]-5-methylhex-2-enoate
• CAS: 1580449-14-4
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: PYKZHKVQPKAMQH-TXBNAWBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl (2E,5S)-6-[(4R)-2,2-dimethyl-1,3-dioxan-4-yl]-5-methylhex-2-enoate 在 咪唑 、 4-二甲氨基吡啶 、 草酰氯 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 (E)-(S)-8-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-7-oxo-oct-2-enoic acid ethyl ester
  参考文献：
  名称：

  (3S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutan-1-ol—A universal building block for the synthesis of principal fragments of amphidinolides G and H

  摘要：

  A new scheme has been proposed for the synthesis of cytotoxic macrocyclic lactones, amphidinolides G and H. Synthetic analogs of the C(7)aEuro'C-14, C(15)aEuro'C-19, and C(20)aEuro'C-26 fragments of amphidinolides G and H have been prepared from the same starting compound, (3S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutan-1-ol. The developed procedures and obtained products may be used in the synthesis of related compounds containing similar structural fragments.

  DOI：

  10.1134/s1070428016010206
• 作为产物：
  描述：

  (3S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutan-1-ol 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 34.0h， 生成 ethyl (2E,5S)-6-[(4R)-2,2-dimethyl-1,3-dioxan-4-yl]-5-methylhex-2-enoate
  参考文献：
  名称：

  (3S,5R)-6-(benzyloxy)-3-methylhexane-1,5-diol in the synthesis of insect pheromones with methyl-branched carbon chain and of amphidinolide L C 7 –C 14 fragment

  摘要：

  New building block (3S,5R)-6-(benzyloxy)-3-methylhexane-1,5-diol was obtained, and based thereon new formal syntheses of (Z)-trogodermal, a component of the sex pheromone of smaller tea tortrix and of the alarm pheromone of ants of genus Crematogaster were suggested. A new synthetic protocol for (3S)-5-methyl-5-oxopentyl acetate and (3S)-5-(benzyloxy)-3-methylpentanal, convenient building blocks for insect pheromones designing was developed. A new simple and efficient asymmetric synthesis of C-7-C-14 fragment of the cytotoxic macrolactone amphidinolide L was carried out.

  DOI：

  10.1134/s1070428014020043