6-Chloro-2-methylhex-4-yn-3-ol | 172978-26-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Chloro-2-methylhex-4-yn-3-ol
• CAS: 172978-26-6
• 化学式: C₇H₁₁ClO
• mdl: MFCD19233898
• 分子量: 146.617
• InChiKey: SDXKGFGBIFEUAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-Chloro-2-methylhex-4-yn-3-ol 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 生成 6-Chloro-2-methyl-4-hexyn-3-one
  参考文献：
  名称：

  Propargyl Chlorides as Sources for Cobalt Stabilized .gamma.-Carbonyl Cations

  摘要：

  Hexacarbonyldicobalt complexes of gamma-chloroalkynones and gamma-chloroalkynoates (5) were found to undergo silver-mediated Nicholas condensation reactions with silyl enol ethers or silyl ketene acetals (10) to give 1,6-dicarbonyl complexes 11 in fair to good yields. Substrates 5 with gamma-alkyl substitution formed diastereomeric products with enol silanes 10a and 10b. Reactions with propiophenone trimethylsilyl enol ether (10b) gave good levels of syn diastereoselection, whereas reactions with cyclohexanone trimethylsilyl enol ether (10a) were only slightly diastereoselective, favoring the anti diastereomer. When conducted in acetonitrile, the silver-mediated reaction of 5e gave a radical dimerization product 13, isolated as the syn diastereomer.

  DOI：

  10.1021/jo00128a022
• 作为产物：
  描述：

  3-氯丙炔 、 异丁醛 在 甲基锂 作用下， 以 乙醚 为溶剂， 生成 6-Chloro-2-methylhex-4-yn-3-ol
  参考文献：
  名称：

  Propargyl Chlorides as Sources for Cobalt Stabilized .gamma.-Carbonyl Cations

  摘要：

  Hexacarbonyldicobalt complexes of gamma-chloroalkynones and gamma-chloroalkynoates (5) were found to undergo silver-mediated Nicholas condensation reactions with silyl enol ethers or silyl ketene acetals (10) to give 1,6-dicarbonyl complexes 11 in fair to good yields. Substrates 5 with gamma-alkyl substitution formed diastereomeric products with enol silanes 10a and 10b. Reactions with propiophenone trimethylsilyl enol ether (10b) gave good levels of syn diastereoselection, whereas reactions with cyclohexanone trimethylsilyl enol ether (10a) were only slightly diastereoselective, favoring the anti diastereomer. When conducted in acetonitrile, the silver-mediated reaction of 5e gave a radical dimerization product 13, isolated as the syn diastereomer.

  DOI：

  10.1021/jo00128a022

文献信息

• Tungsten-Promoted Intramolecular Alkoxycarbonylation for Synthesis of Complex Oxygenated Molecules
  作者：Chi-Chung Chen、Jang-Shyang Fan、Su-Ju Shieh、Gene-Hsian Lee、Shie-Ming Peng、Sue-Lang Wang、Rai-Shung Liu

  DOI：10.1021/ja9617808

  日期：1996.1.1

  Intramolecular alkoxycarbonylation of tungsten-propargyl compounds proceeds with excellent diastereoselectivities to form eta(3)-delta- and -epsilon-lactones but for gamma-lactones. With OSi(t-Bu)Me(2) substituted for an or-hydroxy group, eta(3)-gamma-lactones are stereoselectively formed with syn stereoselection. An optically active tungsten eta(3)-gamma-lactone is prepared from D-(+)-xylose to illustrate the stereochemical effect of OSi(t-Bu)Me(2). All these eta(3)-gamma-, -delta-, and -epsilon-lactones are converted to allyl anions that react in situ with aldehydes and ketones to produce various beta-(hydroxylalkyl)-alpha-methylene-gamma-lactones with good diastereoselectivity. This reaction is also applied to the synthesis of chiral alpha-methylene butyrolactones. Organic carbonyls add to the pi-allyl groups of eta(3)-gamma- and -delta-lactones opposite the tungsten fragment, whereas additions occur from the metal side for eta(3)-epsilon-lactones. The stereochemical courses of these reactions are discussed in detail. These two tungsten-promoted reactions efficiently effect stereoselective transformation of chloroalkynols to complex alpha-methylene-gamma-lactones, which are useful materials for syntheses of trisubstituted 1,3-, 1,4-, and 1-5-diols.
• Propargyl Chlorides as Sources for Cobalt Stabilized .gamma.-Carbonyl Cations
  作者：C. Stephen Vizniowski、James R. Green、Tricia L. Breen、Andrea V. Dalacu

  DOI：10.1021/jo00128a022

  日期：1995.11

  Hexacarbonyldicobalt complexes of gamma-chloroalkynones and gamma-chloroalkynoates (5) were found to undergo silver-mediated Nicholas condensation reactions with silyl enol ethers or silyl ketene acetals (10) to give 1,6-dicarbonyl complexes 11 in fair to good yields. Substrates 5 with gamma-alkyl substitution formed diastereomeric products with enol silanes 10a and 10b. Reactions with propiophenone trimethylsilyl enol ether (10b) gave good levels of syn diastereoselection, whereas reactions with cyclohexanone trimethylsilyl enol ether (10a) were only slightly diastereoselective, favoring the anti diastereomer. When conducted in acetonitrile, the silver-mediated reaction of 5e gave a radical dimerization product 13, isolated as the syn diastereomer.