(E)-8-iodo-6-methyl-1-trimethylsilyl-5-octen-1-yne | 283158-08-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-8-iodo-6-methyl-1-trimethylsilyl-5-octen-1-yne
• 英文别名: (E)-(8-iodo-6-methyloct-5-en-1-yn-1-yl)trimethylsilane；[(E)-8-iodo-6-methyloct-5-en-1-ynyl]-trimethylsilane
• CAS: 283158-08-7
• 化学式: C₁₂H₂₁ISi
• 分子量: 320.289
• InChiKey: CHPBVLAZNBAHPJ-XYOKQWHBSA-N

物化性质

• 沸点：
  283.8±33.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-8-iodo-6-methyl-1-trimethylsilyl-5-octen-1-yne 在 四(三苯基膦)钯 正丁基锂 、 三丁基膦 、 Cu(C₅H₇) 、 叔丁基锂 、 六甲基二锡 、 lithium carbonate 、 氯化铵 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Efficient Assembly of the Phomactin Core via Two Different Macrocyclization Protocols

  摘要：

  [GRAPHICS]The core structure of phomactins C and D was assembled by an efficient strategy starting from 3,4-dimethylcyclohexen-2-one. Key reactions include (1) a high yielding and highly diastereoselective Michael addition of a mixed cuprate, (2) a carbonylative alkyne-enoltriflate coupling or an intramolecular addition of an acetylide onto an aldehyde to form the macrocycle, (3) chemoselective Michael addition of a cuprate to an enynone, to give the carbon framework of desformyl phomactin C or D, and finally (4) regioselective addition of a thia-nucleophile to the more reactive beta -position of the resulting dienone.

  DOI：

  10.1021/ol0163833
• 作为产物：
  描述：

  (E)-3-Methyl-8-trimethylsilanyl-oct-3-en-7-yn-1-ol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-8-iodo-6-methyl-1-trimethylsilyl-5-octen-1-yne
  参考文献：
  名称：

  Efficient Assembly of the Phomactin Core via Two Different Macrocyclization Protocols

  摘要：

  [GRAPHICS]The core structure of phomactins C and D was assembled by an efficient strategy starting from 3,4-dimethylcyclohexen-2-one. Key reactions include (1) a high yielding and highly diastereoselective Michael addition of a mixed cuprate, (2) a carbonylative alkyne-enoltriflate coupling or an intramolecular addition of an acetylide onto an aldehyde to form the macrocycle, (3) chemoselective Michael addition of a cuprate to an enynone, to give the carbon framework of desformyl phomactin C or D, and finally (4) regioselective addition of a thia-nucleophile to the more reactive beta -position of the resulting dienone.

  DOI：

  10.1021/ol0163833

文献信息

• Methyl-Shifted Farnesyldiphosphate Derivatives Are Substrates for Sesquiterpene Cyclases
  作者：Vanessa Harms、Benjamin Schröder、Clara Oberhauser、Cong Duc Tran、Sven Winkler、Gerald Dräger、Andreas Kirschning

  DOI：10.1021/acs.orglett.0c01345

  日期：2020.6.5

  New sesquiterpene backbones are accessible after biotransformation of presilphiperfolan-8 beta-ol synthase (BcBOT2), a fungal sesquiterpene synthase, with non-natural farnesyldiphosphates in which methyl groups are shifted by one position toward the diphosphate terminus. One of the macrocycles formed, a new germacrene A derivative, undergoes a Cope rearrangement to iso-beta-elemene. Three of the new terpenoids show olfactoric properties that range from an intense peppery note to a citrus, ozone-like, and fruity scent.
• A Novel, Highly Selective, and General Methodology for the Synthesis of 1,5-Diene-Containing Oligoisoprenoids of All Possible Geometrical Combinations Exemplified by an Iterative and Convergent Synthesis of Coenzyme Q₁₀
  作者：Ei-ichi Negishi、Show-Yee Liou、Caiding Xu、Shouquan Huo

  DOI：10.1021/ol010263d

  日期：2002.1.1

  GRAPHICSA truly general, versatile, and highly regio- and stereoselective methodology for the synthesis of terpenoids containing 1,5-diene units of E and/or Z geometry critically involves Pd-catalyzed homoallyl- and homopropargyl-alkenyl coupling and Zr-catalyzed carboalumination of alkynes. By using this methodology, coenzyme Q(10), (E,Z,E)-geranylgeranoll, and other natural or unnatural compounds have been synthesized efficiently.