1-(2-丙炔基)环庚醇 | 91055-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-丙炔基)环庚醇
• 英文名称: 1-(2-propynyl)cycloheptanol
• 英文别名: 1-prop-2-ynyl-cycloheptanol；1-Prop-2-inyl-cycloheptanol；1-(Prop-2-yn-1-yl)cycloheptan-1-ol；1-prop-2-ynylcycloheptan-1-ol
• CAS: 91055-74-2
• 化学式: C₁₀H₁₆O
• mdl: MFCD13873732
• 分子量: 152.236
• InChiKey: IVHYZHFFURNOOD-UHFFFAOYSA-N

物化性质

• 沸点：
  49-50 °C(Press: 0.25 Torr)
• 密度：
  0.966±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  1-(2-丙炔基)环庚醇 在 ammonium cerium(IV) nitrate 、 tungsten pentacarbonyl tetrahydrofuran 作用下， 生成 1-氧杂螺[4.6]十一烷-2-酮
  参考文献：
  名称：

  过渡金属在有机合成中促进乙炔异构化反应

  摘要：

  已经开发出过渡金属介导的乙炔-亚乙烯基重排用于合成螺环内酯

  DOI：

  10.1016/s0040-4039(00)73103-0
• 作为产物：
  描述：

  3-溴丙炔 、 环庚酮 在 乙醚 、 magnesium 、 mercury dichloride 作用下， 生成 1-(2-丙炔基)环庚醇
  参考文献：
  名称：

  取代的炔丙基甲醇及其催眠作用†

  摘要：

  通过使炔丙基溴与酮缩合制备了三十种叔炔丙基甲醇。其中一些表现出比3-甲基戊炔-3-01更好的催眠活性。该系列中最好的化合物是1-氯-2-氯甲基戊-4-yn-2-01，事实证明它是一种非常有效的催眠药，具有良好的治疗指数。

  DOI：

  10.1002/hlca.19590420312

文献信息

• Highly Selective Synthesis of Acetylenic Alcohols Promoted by Metallic Dysprosium in the Presence of Mercuric Chloride
  作者：Zhiming Li、Yu Jia、Jingyao Zhou

  DOI：10.1080/00397910008087415

  日期：2000.7

  Abstract Promoted by metallic dysprosium, carbonyl compounds react smoothly with propargyl bromide to afford the corresponding homopropargylic alcohols in good to excellent yields without observation of allenic alcohols. In addition, this reaction is regioselective and chemoselective.

  摘要 在金属镝的促进下，羰基化合物与炔丙基溴顺利反应得到相应的高炔丙醇，收率良好至极好，而没有观察到丙二烯醇。此外，该反应具有区域选择性和化学选择性。
• Ready Access to Benzannulated [5,5]-Oxaspirolactones Using Au(III)-Catalyzed Cascade Cyclizations
  作者：Yash Mankad、Sagar S. Thorat、Pronay Das、Gamidi Rama Krishna、Ravindar Kontham、D. Srinivasa Reddy

  DOI：10.1021/acs.joc.1c02843

  日期：2022.3.4

  showcases an unprecedented Au(III)-catalyzed cascade cyclization of 2-(4-hydroxyalkynyl)benzoates to access benzannulated [5,5]-oxaspirolactones related to biologically active natural products. This reaction proceeds through an initial 5-endo-dig mode of hydroalkoxylation of the alkynol segment to give the oxocarbenium species (via cyclic enol-ether) followed by the addition of carboxylate onto the oxocarbenium

  这项工作展示了史无前例的 Au(III) 催化的 2-(4-羟基炔基)苯甲酸酯的级联环化，以获得与生物活性天然产物相关的苯环 [5,5]-氧杂螺内酯。该反应通过炔醇链段的氢化烷氧基化的初始 5 - endo -dig 模式进行，以产生氧代碳鎓物质（通过环烯醇-醚），然后将羧酸盐添加到氧代碳鎓上，从而递送氧螺内酯支架。在测试该方法的范围时，我们发现羟基的空间位阻和电子环境可以改变通过羧酸盐对束缚炔烃的竞争性 6- endo -dig 攻击模式传递异色烯酮的反应途径。
• Synthesis of Sultones from Chlorosulfates by a Complex Cascade Reaction Occurring under Mild Thermal Conditions
  作者：Lara Cala、Iván Rivilla、Fernando P. Cossío、Francisco J. Fañanás、Félix Rodríguez

  DOI：10.1002/chem.201903228

  日期：2019.10.11

  used to get other sulfur-containing compounds by formal nucleophilic substitution of the chlorine atom. This work describes a different mode of reactivity of alkyne-containing chlorosulfates to get sultones, the sulfur analogues of lactones. The complex skeletal rearrangement observed in this transformation is comparable to those intricate processes promoted or catalyzed by organometallic compounds.

  氯硫酸盐衍生物是令人感兴趣的试剂，传统上已用于通过氯原子的形式亲核取代获得其他含硫化合物。这项工作描述了含炔的氯代硫酸盐得到磺内酯（内酯的硫类似物）的不同反应方式。在这种转化过程中观察到的复杂骨架重排与有机金属化合物促进或催化的复杂过程相当。然而，这里描述的反应不需要任何试剂或添加剂，仅是热处理。计算计算支持一种基于一系列级联反应的机制，其中几乎每个步骤都是违反直觉的。其中一些步骤包括与经典反应相关的原始过程，
• 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.
• 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.