(-)-isodactylyne | 58001-90-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (-)-isodactylyne
• 英文别名: (2R,3R,5S,6S)-3-bromo-2-[(E)-3-bromopent-2-enyl]-5-chloro-6-[(E)-pent-2-en-4-ynyl]oxane
• CAS: 58001-90-4
• 化学式: C₁₅H₁₉Br₂ClO
• 分子量: 410.576
• InChiKey: NZHWXNQBZKBACG-YYTOSCLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2R,3R,5S,6S)-3-bromo-6-<(2'E)-5'-t-butyldimethylsilyl-2'-pentenynyl>-5-chloro-2-(2'-hydroxyethyl)tetrahydropyran 在 正丁基锂 、 Swern oxid 、 氢氟酸 、 四丁基氟化铵 作用下， 反应 2.75h， 生成 (-)-isodactylyne
  参考文献：
  名称：

  Total synthesis of (−)-dactylyne and (−)-isodactylyne

  摘要：

  The first total synthesis of (-)-dactylyne (1) and (-)-isodactylyne (2), which are isolated from sea hare, is described via intermediates 3-15 and 17-18. Critical steps in the synthesis include a stereoselective construction as well as an intramolecular ring closure of 12, and the effective double elongation reactions (15 --> 17 and 17 --> 18).

  DOI：

  10.1016/s0040-4039(00)74257-2

文献信息

• Total synthesis of (−)-dactylyne and (−)-isodactylyne
  作者：Lian-xun Gao、Akio Murai

  DOI：10.1016/s0040-4039(00)74257-2

  日期：1992.7

  The first total synthesis of (-)-dactylyne (1) and (-)-isodactylyne (2), which are isolated from sea hare, is described via intermediates 3-15 and 17-18. Critical steps in the synthesis include a stereoselective construction as well as an intramolecular ring closure of 12, and the effective double elongation reactions (15 --> 17 and 17 --> 18).
• Total Synthesis of (-)-Dactylynes
  作者：Akio Murai、Lian-xun Gao

  DOI：10.3987/com-95-s84

  日期：——