7-epi-(1S,3R,5R,7R)-(-)-sordinin | 162428-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 7-epi-(1S,3R,5R,7R)-(-)-sordinin
• 英文别名: (1S,3R,5R,7R)-1-ethyl-3,5,7-trimethyl-2,8-dioxabicyclo[3.2.1]octane
• CAS: 162428-76-4
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: LOGJGKGBKZOEKZ-DBIOUOCHSA-N

物化性质

• 沸点：
  211.3±8.0 °C(Predicted)
• 密度：
  0.959±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,1-二甲基-2-(1-乙基亚丙基)肼 在 正丁基锂 、 tert-butyl-ammonium fluoride 、 silica gel 作用下， 以 四氢呋喃 为溶剂， 生成 7-epi-(1S,3R,5R,7R)-(-)-sordinin
  参考文献：
  名称：

  Absolute configuration of sordidin and 7-episordidin emitted by the banana weevil, Cosmopolites sordidus

  摘要：

  Male-specific volatile components released by the banana weevil, Cosmopolites sordidus Germar, from Australia have been identified as (1S,3R,5R,7S)-1-ethyl-3,5,7-trimethyl-2, and the 7R-epimer (as a minor component) by synthesis and enantioselective gas chromatography. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00659-x

文献信息

• Synthesis of (1<i>S</i>,3<i>R</i>,5<i>R</i>,7<i>S</i>)-Sordidin, the Main Component of the Aggregation Pheromone of the Banana Weevil <i>Cosmopolites sordidus</i>
  作者：Lars Skattebøl、Kamilla Lundhaug、Arne Aasen

  DOI：10.1055/s-0028-1087373

  日期：——

  A synthesis of the banana weevil pheromone component (1 S,3 R,5 R,7 S)-sordidinstarting from ( S)-2-(2-ethyl-1,3-dioxolanyl)propan-1-oland ( R)-4-hydroxypentan-2-one is described.No epimerization was observed for the final, intramolecular, acid-catalyzedcyclization step using aqueous oxalic acid.

  从 (S)-2-(2-ethyl-1,3-dioxolanyl)propan-1-oland (R)-开始合成香蕉象鼻虫信息素成分 (1 S,3 R,5 R,7 S)-sordidin描述了 4-羟基戊烷-2-one。对于使用草酸水溶液的最终的、分子内的、酸催化的环化步骤没有观察到差向异构化。
• First Asymmetric Synthesis of (+)-Sordidin and (-)-7-epi-Sordidin, Aggregation Pheromones of the Banana WeevilCosmopolites sordidus
  作者：Dieter Enders、Irene Breuer、Anja Nühring

  DOI：10.1002/ejoc.200500112

  日期：2005.7

  The asymmetric synthesis of (1S,3R,5R,7S)-(+)-sordidin and 7-epi-(1S,3R,5R,7R)-(–)-sordidin, both components of the natural male-produced aggregation pheromone of the banana weevil Cosmopolites sordidus (Germar), starting from 2,2-dimethyl-1,3-dioxan-5-one is described. Two of the stereogenic centers were generated by three α-alkylations of the corresponding RAMP-hydrazone. Diastereoselective epoxide

  (1S,3R,5R,7S)-(+)-sordidin 和 7-epi-(1S,3R,5R,7R)-(-)-sordidin 的不对称合成，这两种天然雄性聚集信息素的成分描述了从 2,2-二甲基-1,3-二恶烷-5-one 开始的香蕉象鼻虫 Cosmopolites sordidus (Germar)。两个立体中心由相应的 RAMP-腙的三个 α-烷基化产生。非对映选择性环氧化物开放是合成的另一个关键步骤，使用 3-戊酮 SAEP-腙的氮杂烯醇化物作为亲核试剂，随后的酸性分子内缩醛化以良好的总产率 (39%) 提供了 sordidin C-7 差向异构体，为 1.5:1 非对映异构体混合物。差向异构体可以通过制备型 GC 进行分离，因此，它们中的每一个都可以获得高非对映体和对映体纯度（de ≥ 97 %，ee ≥ 98 %）。
• Identification and synthesis of sordidin, a male pheromone emitted by Cosmopolites sordidus
  作者：Josiane Beauhaire、Paul-Henri Ducrot、Christian Malosse、Didier Rochat、Isaiah O. Ndiege、Dalmas O. Otieno

  DOI：10.1016/0040-4039(94)02437-g

  日期：1995.2

  The diastereoselective synthesis of (1S∗, 3R∗, 5R∗, 7S∗) 2,8-dioxa 1-ethyl 3,5,7-trimethyl bicylo [3,2,1] octane 1d has been achieved using as key-step the regioselective Baeyer-Villiger reaction of 2,6-disubstituted cyclohexanone. It confirms the identification of a new male pheromone emitted by the banana weevil, Cosmopolites sordidus. The trivial name sordidin is proposed.

  （1S ∗，3R ∗，5R ∗，7S ∗）2,8-二氧杂-1-乙基1,3,5,7-三甲基双环[3,2,1]辛烷1d的非对映选择性合成已通过关键步骤完成2,6-二取代的环己酮的区域选择性Baeyer-Villiger反应。它证实了由香蕉象鼻虫Cosmopolites sordidus发出的新的雄性信息素的鉴定。建议使用平凡的名称sordidin。
• Synthesis and absolute configuration of sordidin, the male-produced aggregation pheromone of the banana weevil, Cosmopolites sordidus
  作者：Kenji Mori、Tôru Nakayama、Hirosato Takikawa

  DOI：10.1016/0040-4039(96)00674-0

  日期：1996.5

  The racemate as well as both the enantiomers of sordidin (1-ethyl-3,5,7-trimethyl-2,8-dioxabicyclo[3.2.1]octane, 1) were synthesized, and the natural pheromone was shown to be (1S,3R,5R,7S)-(+)-1.

  合成了索迪定的外消旋体和两个对映体（1-乙基-3,5,7-三甲基-2,8-二恶双环[3.2.1]辛烷，1），天然信息素显示为（1S ，3R，5R，7S）-（+）-1 。
• Pheromone Synthesis, CLXXXIV. Synthesis and Absolute Configuration of Sordidin, the Male-Produced Aggregation Pheromone of the Banana Weevil,cosmopolites sordidus
  作者：T??Ru Nakayama、Kenji Mori

  DOI：10.1002/jlac.199719970605

  日期：1997.6

  The racemate as well as both the enantiomers of sordidin (1-ethyl-3,5,7-trimethyl-2,8-dioxabicyclo[3.2.1])octane were synthesized, and the natural pheromone was shown to be (1S,3R,5R,7S)-(+)-1.

  合成了索迪定（1-乙基-3,5,7-三甲基-2,8-二氧杂双环[3.2.1]）辛烷的外消旋体和两种对映体，其天然信息素显示为（1 S， 3 R，5 R，7 S）-（+）- 1。