2-methyl-5-octyn-3-ol | 383135-85-1

• 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: 2-methyl-5-octyn-3-ol
• 英文别名: 2-Methyloct-5-yn-3-ol
• CAS: 383135-85-1
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: JTPWBWSRKUYKNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  2-methyl-5-octyn-3-ol 在 咪唑 、 palladium diacetate 、 1,1,3,3-四甲基丁基异腈 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.0h， 生成 (Z)-3-<(dimethylphenylsilyl)propylidene>-5-isopropyl-2,2-dimethyl-1,2-oxasilolane
  参考文献：
  名称：

  通过碳碳三键的分子内双甲硅烷基化和氢化反应来立体选择性合成1,2,4-三醇

  摘要：

  已经开发了1,2,4-三醇立体选择性合成的新策略。在用乙酸钯和叔烷基异氰化物处理后，被束缚至二硅烷基的炔烃提供了环外双甲硅烷基化的烯烃。随后从环的受阻较弱的一侧进行氢化，生成顺式-二取代的氧杂硅烷基。氢化恶唑烷烃的两个CSi键的氧化导致1,2,4-三醇的立体和区域确定的合成。

  DOI：

  10.1016/s0040-4020(01)89908-7
• 作为产物：
  描述：

  异丁醛 、 tetrapent-2-ynylstannane 以 甲醇 为溶剂， 生成 2-methyl-5-octyn-3-ol 、 3-ethyl-5-methyl-1,2-hexadien-4-ol
  参考文献：
  名称：

  A Highly Atom Efficient, Solvent Promoted Addition of Tetraallylic, Tetraallenic, and Tetrapropargylic Stannanes to Carbonyl Compounds

  摘要：

  Tetraallylic, tetraallenic, and tetrapropargylic stannanes (0.25 equiv) react with aldehydes in methanol to provide unsaturated alcohols in good to excellent yields (56-99%). These reactions proceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)tin 16c and predominantly with allylic rearrangement for tetrapropadienyltin 16a and tetra(2-butynyl)tin 6e. Allylation. reactions also proceeded smoothly with reactive ketones such as ethyl pyruvate (9a) and cyclohexanone (9b). The corresponding TFA-catalyzed reactions of dimethyl acetals 4d and 4e are regiospecific with allylic rearrangement.

  DOI：

  10.1021/jo015904x

文献信息

• A Highly Atom Efficient, Solvent Promoted Addition of Tetraallylic, Tetraallenic, and Tetrapropargylic Stannanes to Carbonyl Compounds
  作者：Adam McCluskey、I. Wayan Muderawan、Muntari、David J. Young

  DOI：10.1021/jo015904x

  日期：2001.11.1

  Tetraallylic, tetraallenic, and tetrapropargylic stannanes (0.25 equiv) react with aldehydes in methanol to provide unsaturated alcohols in good to excellent yields (56-99%). These reactions proceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)tin 16c and predominantly with allylic rearrangement for tetrapropadienyltin 16a and tetra(2-butynyl)tin 6e. Allylation. reactions also proceeded smoothly with reactive ketones such as ethyl pyruvate (9a) and cyclohexanone (9b). The corresponding TFA-catalyzed reactions of dimethyl acetals 4d and 4e are regiospecific with allylic rearrangement.
• Stereoselective synthesis of 1,2,4-triols via intramolecular bis-silylation of CarbonCarbon triple bonds followed by hydrogenation
  作者：Masahiro Murakami、Hideaki Oike、Mitsuru Sugawara、Michinori Suginome、Yoshihiko Ito

  DOI：10.1016/s0040-4020(01)89908-7

  日期：1993.5

  new strategy for the stereoselective synthesis of 1,2,4-triols has been developed. An alkyne tethered to a disilanyl group, upon treatment with palladium acetate and tert-alkyl isocyanide, furnished an exocyclic bis-silylated olefin. Subsequent hydrogenation took place from the less-hindered side of the ring producing cis-disubstituted oxasilolane. Oxidation of the two CSi bonds of the hydrogenated

  已经开发了1,2,4-三醇立体选择性合成的新策略。在用乙酸钯和叔烷基异氰化物处理后，被束缚至二硅烷基的炔烃提供了环外双甲硅烷基化的烯烃。随后从环的受阻较弱的一侧进行氢化，生成顺式-二取代的氧杂硅烷基。氢化恶唑烷烃的两个CSi键的氧化导致1,2,4-三醇的立体和区域确定的合成。