methyl (Z)-7-[(R)-2,2-diethyl-1,3-dioxolan-4-yl]-5-heptenoate | 1610421-77-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (Z)-7-[(R)-2,2-diethyl-1,3-dioxolan-4-yl]-5-heptenoate
• CAS: 1610421-77-6
• 化学式: C₁₅H₂₆O₄
• 分子量: 270.369
• InChiKey: XTAZNSODCCGGAM-FWPCIQOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  methyl (Z)-7-[(R)-2,2-diethyl-1,3-dioxolan-4-yl]-5-heptenoate 在 amberlite IR-120 plus 作用下， 以 甲醇 、 水 为溶剂， 反应 15.0h， 生成 methyl (5Z,8R)-8,9-dihydroxynon-5-enoate
  参考文献：
  名称：

  Synthesis of topsentolides A2 and C2, and non-enzymatic conversion of the former to the latter

  摘要：

  The first total synthesis of the marine-derived cytotoxin topsentolide A(2), which eventually culminated in its stereochemical determination, was accomplished in 17 steps from a known chiral alcohol. An improved synthesis of its congener, topsentolide C-2, from a synthetic intermediate of topsentolide A(2) was also performed by utilizing the Yamaguchi lactonization to construct its nine-membered lactone ring. Treatment of epoxide ring-containing topsentolide Ay with HCl/MeOH brought about its quantitative conversion into topsentolide C-2. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.040
• 作为产物：
  描述：

  2,2-Diethyl-4-(2-iodoethyl)-1,3-dioxolane 在 sodium hexamethyldisilazane 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 17.0h， 生成 methyl (Z)-7-[(R)-2,2-diethyl-1,3-dioxolan-4-yl]-5-heptenoate
  参考文献：
  名称：

  Synthesis of topsentolides A2 and C2, and non-enzymatic conversion of the former to the latter

  摘要：

  The first total synthesis of the marine-derived cytotoxin topsentolide A(2), which eventually culminated in its stereochemical determination, was accomplished in 17 steps from a known chiral alcohol. An improved synthesis of its congener, topsentolide C-2, from a synthetic intermediate of topsentolide A(2) was also performed by utilizing the Yamaguchi lactonization to construct its nine-membered lactone ring. Treatment of epoxide ring-containing topsentolide Ay with HCl/MeOH brought about its quantitative conversion into topsentolide C-2. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.040