methyl 6-cyclohexylhex-5-ynoate | 211820-36-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 6-cyclohexylhex-5-ynoate
• CAS: 211820-36-9
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: MWHCLMWAHCSNKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 6-cyclohexylhex-5-ynoate 在 lithium aluminium tetrahydride 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 生成 (2S,3R)-2-(4-cyclohexylbut-3-ynyl)pent-4-ene-1,3-diol
  参考文献：
  名称：

  Sequential Cyclization/Silylation of Dienynes Catalyzed by an Organoyttrium Complex

  摘要：

  The organoyttrium complex Cp*2YCH3. THF (Cp* = C5Me5) has been shown to be an effective precatalyst for the selective sequential cyclization/silylation of dienynes. The catalyst's ability to insert the alkyne in preference to the alkenes in a regioselective manner, combined with the high diastereoselectivity of the intramolecular insertion process, leads to bicyclo[3.3.0]octane products in high yield. The stereochemistry of the exocyclic olefin, the ring fusion, and the ring substituents are all controlled in the reaction. The cyclization of dienynes thus affords silylated carbobicyclics with high diastereoselectivities in excellent yields.

  DOI：

  10.1021/jo980521t
• 作为产物：
  描述：

  6-Cyclohexyl-hex-5-yn-1-ol 在 4-二甲氨基吡啶 、 重铬酸吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 6-cyclohexylhex-5-ynoate
  参考文献：
  名称：

  Sequential Cyclization/Silylation of Dienynes Catalyzed by an Organoyttrium Complex

  摘要：

  The organoyttrium complex Cp*2YCH3. THF (Cp* = C5Me5) has been shown to be an effective precatalyst for the selective sequential cyclization/silylation of dienynes. The catalyst's ability to insert the alkyne in preference to the alkenes in a regioselective manner, combined with the high diastereoselectivity of the intramolecular insertion process, leads to bicyclo[3.3.0]octane products in high yield. The stereochemistry of the exocyclic olefin, the ring fusion, and the ring substituents are all controlled in the reaction. The cyclization of dienynes thus affords silylated carbobicyclics with high diastereoselectivities in excellent yields.

  DOI：

  10.1021/jo980521t

文献信息

• Photoinduced Copper‐Catalyzed Coupling of Terminal Alkynes and Alkyl Iodides
  作者：Avijit Hazra、Mitchell T. Lee、Justin F. Chiu、Gojko Lalic

  DOI：10.1002/anie.201801085

  日期：2018.5.4

  We have developed a photoinduced copper‐catalyzed alkylation of terminal alkynes with primary, secondary, or tertiary alkyl iodides as electrophiles. The reaction has a broad substrate scope and can be successfully performed in the presence of ester, nitrile, aryl halide, ketone, sulfonamide, epoxide, alcohol, and amide functional groups. The alkylation is promoted by blue light (λ≈450 nm) and proceeds

  我们已经开发出了以伯，仲或叔烷基碘为亲电试剂的末端炔烃的光诱导铜催化烷基化反应。该反应具有广泛的底物范围，并且可以在酯，腈，卤代芳基，酮，磺酰胺，环氧化物，醇和酰胺官能团的存在下成功进行。该烷基化是由蓝色光促进（λ ≈450nm）与在没有任何附加的金属催化剂的室温下进行。联吡啶配体的使用对于反应的成功至关重要，而且可以防止光诱导的铜催化原料的聚合。
• Sequential Cyclization/Silylation of Dienynes Catalyzed by an Organoyttrium Complex
  作者：Gary A. Molander、William H. Retsch

  DOI：10.1021/jo980521t

  日期：1998.8.1

  The organoyttrium complex Cp*2YCH3. THF (Cp* = C5Me5) has been shown to be an effective precatalyst for the selective sequential cyclization/silylation of dienynes. The catalyst's ability to insert the alkyne in preference to the alkenes in a regioselective manner, combined with the high diastereoselectivity of the intramolecular insertion process, leads to bicyclo[3.3.0]octane products in high yield. The stereochemistry of the exocyclic olefin, the ring fusion, and the ring substituents are all controlled in the reaction. The cyclization of dienynes thus affords silylated carbobicyclics with high diastereoselectivities in excellent yields.