4-甲基-1-庚炔-4-醇 | 68274-80-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-甲基-1-庚炔-4-醇
• 英文名称: 4-methyl-1-heptyn-4-ol
• 英文别名: 4-methyl-hept-1-yn-4-ol；4-Methyl-hept-1-in-4-ol；(+/-)-4-Methyl-heptin-(1)-ol-(4)；4-Methylhept-1-yn-4-ol
• CAS: 68274-80-6
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: DPZSISAWBIQWLF-UHFFFAOYSA-N

物化性质

• 沸点：
  75 °C(Press: 45 Torr)
• 密度：
  0.889±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  4-甲基-1-庚炔-4-醇 在 tris(dibenzylideneacetone)dipalladium (0) 作用下， 以 四氢呋喃 、 氘代甲苯 为溶剂， 反应 22.0h， 生成 (E)-2-diisopropylamino-5-methyl-5-propyl-3-cyanomethylene-1,2-oxaborolane
  参考文献：
  名称：

  通过过渡金属催化剂活化硼-氰化物键使炔烃的分子内氰基化

  摘要：

  在钯和镍催化剂的存在下，高炔丙醇的氰基（二烷基氨基）硼醚在其碳-碳三键上进行B-CN键的分子内加成（氰基化），通过5选择性地高产率提供五元环状硼醚-exo环化。产物通过Suzuki-Miyaura与芳基碘化物的偶联，铑催化的对甲基乙烯基酮的共轭加成以及铑催化的原基脱硼化作用，转变为高度取代的α，β-不饱和腈。

  DOI：

  10.1016/j.jorganchem.2005.05.005
• 作为产物：
  描述：

  2-戊酮 、 3-溴丙炔 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以70.1%的产率得到4-甲基-1-庚炔-4-醇
  参考文献：
  名称：

  叔醇类化合物的制备方法

  摘要：

  本发明公开了一种叔醇类化合物的制备方法，该方法包括：(1)将格氏试剂与式2所示反应底物接触引发反应；(2)继续加入所述式2所示反应底物和所述格氏试剂，以便生成式1所示叔醇类化合物，其中，R1和R2分别独立地为C1‑C4直链饱和烃基或者不饱和烃基。利用本发明提供的方法，操作简便，使格氏反应过程能被有效控制且能得到高纯度和高收率的目标产物，从而使工业化生产过程安全实现。

  公开号：

  CN106117009A

文献信息

• Palladium- and Nickel-Catalyzed Intramolecular Cyanoboration of Alkynes
  作者：Michinori Suginome、Akihiko Yamamoto、Masahiro Murakami

  DOI：10.1021/ja0349195

  日期：2003.5.1

  Intramolecular addition of a boron-cyano bond across a carbon-carbon triple bond was achieved using palladium and nickel catalysts. Cyano(diisopropylamino)boryl homopropargyl ethers underwent regio- and stereoselective 5-exo cyclization, forming five-membered cyclic boryl ethers in high yields. The cyanoboration products thus obtained served as new precursors for the synthesis of highly substituted

  使用钯和镍催化剂实现了跨越碳-碳三键的硼-氰基键的分子内加成。氰基（二异丙基氨基）硼基高炔丙基醚经过区域选择性和立体选择性 5-外环化，以高产率形成五元环状硼基醚。由此获得的氰基硼化产物用作通过过渡金属催化转化合成高度取代的 α,β-不饱和腈的新前体。
• Synth�se d'alcools ac�tyl�niques par alkylation d'hydroxy-?-alkynes-1
  作者：Jacques Flahaut、Philippe Miginiac

  DOI：10.1002/hlca.19780610635

  日期：1978.9.20

  Synthesis of acetylenic alcohols by alkylation of ω‐hydroxy‐1‐alkynesIn liquid ammonia and with lithium amide, the alkylation of an ω‐hydroxyl‐alkyne proceeds with good yield with primary or secondary alcohols and with fair yield with tertiary alcohols. It is a very convenient way to prepare many substituted acetylenic alcohols.
• The Prevalence of Daytime Napping and Its Relationship to Nighttime Sleep
  作者：June J. Pilcher、Kristin R. Michalowski、Renee D. Carrigan

  DOI：10.1080/08964280109595773

  日期：2001.1

  Many healthy adults report daytime napping. Surprisingly few studies, however have examined spontaneous napping behavior especially very short naps, in healthy adults. The authors examined the prevalence of power naps (lasting less than 20 minutes) and longer naps (20 minutes or more) and their effects on nighttime sleep in a group of healthy young and middle-aged adults. The young and middle-aged adults reported very similar sleep and napping patterns, with approximately 74% of the participants in both groups reporting they had napped during a 7-day sleep-log period. Almost half of the participants reported that the average nap lasted less than 20 minutes. A multivariant analysis of variance (MANOVA) found no significant differences between the no-nap and the power-nap or long-nap groups in sleep quantity or quality for either age group. The current data suggested that power napping occurs frequently in healthy adults and that spontaneous napping does not negatively affect nighttime sleep.
• Fontaine,G. et al., Bulletin de la Societe Chimique de France, 1963, p. 1444 - 1448
  作者：Fontaine,G. et al.

  DOI：——

  日期：——
• A New Synthesis of γ-Butyrolactones via AuCl₃- or Hg(II)-Catalyzed Intramolecular Hydroalkoxylation of 4-Bromo-3-yn-1-ols
  作者：Maddi Sridhar Reddy、Yalla Kiran Kumar、Nuligonda Thirupathi

  DOI：10.1021/ol2033493

  日期：2012.2.3

  An efficient conversion of 4-bromo-3-yn-1-ols to gamma-butyrolactones via AuCl3-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with moderate to excellent yields obtained in all cases.