5-cyclohexyl-4-pentynal | 195535-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-cyclohexyl-4-pentynal
• 英文别名: 5-Cyclohexylpent-4-ynal
• CAS: 195535-10-5
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: VZFKIYJGNAOTBA-UHFFFAOYSA-N

物化性质

• 沸点：
  261.6±19.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-cyclohexyl-4-pentynal 在 lithium aluminium tetrahydride 、 (C₅Me₅)2YCH₃*THF 作用下， 以 四氢呋喃 、 氘代苯 为溶剂， 反应 0.5h， 生成 2-{(1S,2S)-3-[1-Cyclohexyl-meth-(E)-ylidene]-2-phenylsilanylmethyl-cyclopentyl}-2,3-dihydro-1H-isoindole
  参考文献：
  名称：

  Sequential Cyclization/Silylation of Enynes 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 1,6- and 1,7-enynes.. The catalyst's ability to insert the alkyne in preference to the alkene in a regioselective manner, combined with the high diastereoselectivity of the insertion process, yields a product with only one stereochemistry about the exocyclic olefin. The reaction proceeds under extremely mild conditions with short reaction times. Cyclization of enynes functionalized in the allylic position affords silylated carbocycles with high diastereoselectivities and excellent yields.

  DOI：

  10.1021/ja971538g
• 作为产物：
  描述：

  三环己基硼烷 在 sodium hydroxide 、 正丁基锂 、 四丁基氟化铵 、 双氧水 、 碘 、 三氧化硫吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 5-cyclohexyl-4-pentynal
  参考文献：
  名称：

  Sequential Cyclization/Silylation of Enynes 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 1,6- and 1,7-enynes.. The catalyst's ability to insert the alkyne in preference to the alkene in a regioselective manner, combined with the high diastereoselectivity of the insertion process, yields a product with only one stereochemistry about the exocyclic olefin. The reaction proceeds under extremely mild conditions with short reaction times. Cyclization of enynes functionalized in the allylic position affords silylated carbocycles with high diastereoselectivities and excellent yields.

  DOI：

  10.1021/ja971538g

文献信息

• 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.
• Synthesis of substituted 6-imino-2-piperidinones by Rh-catalyzed [4+2] annulation of 4-alkynals with carbodiimides
  作者：Ken Tanaka、Marina Mimura、Daiki Hojo

  DOI：10.1016/j.tet.2009.06.115

  日期：2009.10

  Synthesis of substituted 6-imino-2-piperidinones has been achieved by cationic rhodium(1)/dppp complex-catalyzed [4+2] annulations of various 4-alkynals with carbodiimides at room temperature. The reactions of benzene-linked 4-alkynals (2-alkynylbenzaldehydes) and carbodiimides also proceeded at room temperature, affording the corresponding 6-imino-2-piperidinones. (C) 2009 Elsevier Ltd. All rights reserved.