(1SR,6RS)-methyl 9-methylene-2-oxo-3-oxabicyclo[4.3.0]nonane-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1SR,6RS)-methyl 9-methylene-2-oxo-3-oxabicyclo[4.3.0]nonane-1-carboxylate
• 英文别名: methyl (4aR,7aS)-7-methylidene-1-oxo-4,4a,5,6-tetrahydro-3H-cyclopenta[c]pyran-7a-carboxylate
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: HVENCMXYFHLBLT-LDYMZIIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1SR,6RS)-methyl 9-methylene-2-oxo-3-oxabicyclo[4.3.0]nonane-1-carboxylate 在 叔丁基过氧化氢 、 六甲基磷酰三胺 、 selenium(IV) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到(1SR,6SR)-methyl 8-hydroxy-9-methylene-2-oxo-3-oxabicyclo[4.3.0]nonane-1-carboxylate
  参考文献：
  名称：

  THE FIRST TOTAL SYNTHESES OF SCHOLAREINS A, C, AND D EMPLOYING 2ND GENARATION PALLADIUM-CATALYZED CYCLOALKENYLATION

  摘要：

  (±)-Scholareins A（1）、C（3）和D（4）首次通过第二代钯催化的环己烯基化反应成功合成。此外，通过采用相同的催化环化反应作为关键步骤，(±)-boonein（5）的全合成也得以实现。

  DOI：

  10.3987/com-12-s(n)52
• 作为产物：
  描述：

  Methyl 4-but-3-enyl-2-oxooxane-3-carboxylate 在 氧气 、 palladium diacetate 作用下， 以 二甲基亚砜 为溶剂， 45.0 ℃ 、101.33 kPa 条件下， 以69%的产率得到(1SR,6RS)-methyl 9-methylene-2-oxo-3-oxabicyclo[4.3.0]nonane-1-carboxylate
  参考文献：
  名称：

  Development of palladium(II)-catalyzed oxidative cyclization of olefinic keto and/or lactone esters

  摘要：

  A highly efficient palladium-catalyzed oxidative cyclization of olefinic keto and/or lactone esters, which features a catalytic cyclization employing one atmosphere of oxygen as a reoxidizing agent, is developed. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.052

文献信息

• Second Generation Palladium-Catalyzed Cycloalkenylation in Iridoid Lactone Synthesis: Total Syntheses of (±)-Onikulactone and (±)-Mitsugashiwalactone
  作者：Masahiro Toyota、Megumi Saeki

  DOI：10.3987/com-10-s(e)115

  日期：——

  Type-II iridoid lactones, onikulactone (1) and mitsugashiwalactone (2), were synthesized by employing the second generation palladium-catalyzed cycloalkenylation reaction as the key step.
• Development of palladium(II)-catalyzed oxidative cyclization of olefinic keto and/or lactone esters
  作者：Ayaka Hibi、Masahiro Toyota

  DOI：10.1016/j.tetlet.2009.06.052

  日期：2009.8

  A highly efficient palladium-catalyzed oxidative cyclization of olefinic keto and/or lactone esters, which features a catalytic cyclization employing one atmosphere of oxygen as a reoxidizing agent, is developed. (c) 2009 Elsevier Ltd. All rights reserved.
• THE FIRST TOTAL SYNTHESES OF SCHOLAREINS A, C, AND D EMPLOYING 2ND GENARATION PALLADIUM-CATALYZED CYCLOALKENYLATION
  作者：Masahiro Toyota、Yasufumi Kawai、Megumi Saeki

  DOI：10.3987/com-12-s(n)52

  日期：——

  (+/-)-Scholareins A (1), C (3), and D (4) have been synthesized for the first time by a 2nd generation palladium-catalyzed cycloalkenylation. In addition, total synthesis of (+/-)-boonein (5) has also been achieved by applying the same catalytic cyclization as the key step.

  (±)-Scholareins A（1）、C（3）和D（4）首次通过第二代钯催化的环己烯基化反应成功合成。此外，通过采用相同的催化环化反应作为关键步骤，(±)-boonein（5）的全合成也得以实现。