6-phenylhex-5-yn-2-ol | 24595-57-1

• 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: 6-phenylhex-5-yn-2-ol
• CAS: 24595-57-1
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: DBRFWONAXCPHHP-UHFFFAOYSA-N

物化性质

• 沸点：
  304.8±25.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-phenylhex-5-yn-2-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到(+/-)-(E)-6-phenylhex-5-en-2-ol
  参考文献：
  名称：

  使用Sonogashira-硒醚化策略轻松合成芳基二氢吡喃

  摘要：

  据报道，高产率且方便地合成2-芳基-2，5-二氢-2 H-吡喃。4-戊炔-1-醇和5-己炔-2-醇与一定范围的苯基和萘基溴的Sonogashira偶联产生适当的芳基炔醇，然后将其立即还原成相应的（E）-1-芳基-5-羟基烯烃。（E）-5-羟基烯烃的随后的醚醚化通过6-内-trig途径进行，干净地得到反式-2-芳基-3-苯基硒基四氢吡喃。最后氧化消除硒化物，得到2-芳基-2,5-二氢-2 H-吡喃，它们是合成C的方便中间体-芳基糖苷含有双键，可用于进一步的氧合。

  DOI：

  10.1016/s0040-4039(02)00065-5
• 作为产物：
  描述：

  5-苯基-4-戊炔-1-醇 在 pyridinium chlorochromate 作用下， 生成 6-phenylhex-5-yn-2-ol
  参考文献：
  名称：

  Relative Asymmetric Induction in the Intramolecular Reaction between Alkynes and Cyclopropylcarbene−Chromium Complexes:  Stereocontrolled Synthesis of Five-Membered Rings Fused to Oxygen Heterocycles

  摘要：

  Synthesis of cyclopentenone derivatives fused to oxygen heterocycles by means of the intramolecular coupling of alkynes and cyclopropylcarbene-chromium complexes has been examined for a variety of cases in which the tethering chain features a stereogenic center. In some cases, this process proceeds with a very high degree of stereoselectivity; however, the extent and direction of relative asymmetric induction is very dependent upon the position of the chiral atom within the tethering chain and the length of the tethering chain. In the best case, featuring a two-carbon tether and a stereogenic center at the homopropargylic position (complex 1N), the heterocyclic ring was produced with 97:3 selectivity for the cis heterocycle (3N). In the worst case, featuring a three-carbon tether and a stereogenic center at the homopropargylic position (complexes 1F and ii), no stereoselectivity was observed. Improvement in stereoselectivity was noticed when terminal alkynes were replaced by silylated alkynes and when proton sources were eliminated from the reaction.

  DOI：

  10.1021/jo982144q

文献信息

• Lewis Acid Mediated “<i>endo-dig</i>” Hydroalkoxylation–Reduction on Internal Alkynols for the Stereoselective Synthesis of Cyclic Ethers and 1,4-Oxazepanes
  作者：Santosh J. Gharpure、Dharmendra S. Vishwakarma、Santosh K. Nanda

  DOI：10.1021/acs.orglett.7b03241

  日期：2017.12.15

  Lewis acid mediated 5/6/7-endo-dig hydroalkoxylation–reduction cascade on internal alkynols gave an expedient, stereoselective synthesis of cyclic ethers and 1,4-oxazepanes. The strategy has been extended to the first examples of hydroalkoxylation–alkyne Prins-type cyclization cascade of alkyne-tethered alkynols, giving access to oxa-bicyclic scaffolds. This method was used as the key step in the stereoselective

  路易斯酸介导的5/6 / 7-内切挖内部炔醇hydroalkoxylation还原级联得到一个有利的，环醚和1,4- oxazep​​anes的立体选择性合成。该策略已扩展到炔烃系链炔​​醇的加氢烷氧基化-炔烃Prins型环化级联的第一个实例，从而可以使用氧杂双环骨架。该方法被用作花环烷AB以及（±）-中心洛宾及其同系物的立​​体选择性全合成中的关键步骤。
• Divergent Synthesis of Oxepino-Phthalides and [5,5]-Oxaspirolactones through [2 + 2 + 2]- and [2 + 3]-Annulation of Alkynyl Alcohols with α-Ynone-Esters
  作者：Digambar A. Kambale、Balasaheb R. Borade、Ramavath Vinodkumar、Ravindar Kontham

  DOI：10.1021/acs.joc.3c01301

  日期：2023.9.1

  Unmasking the synthetic potential of alkyne functional group of alkynyl alcohols as surrogates of carbonyl compounds, herein we present the first Brønsted acid (TfOH)-catalyzed [2 + 2 + 2]-annulation of 4-pentyn-1-ols (possessing terminal alkyne) with α-ynone-esters to access tricyclic tetrahydro-oxepino-phthalides. Besides, an unprecedented synthesis of α-acetoaryl or α-alkynyl [5,5]-oxaspirolactones

  揭示了炔醇的炔官能团作为羰基化合物替代物的合成潜力，本文中我们提出了第一个布朗斯台德酸（TfOH）催化的 4-戊炔-1-醇（具有末端炔烃）的 [2 + 2 + 2]-环化反应)与α-炔酮-酯反应得到三环四氢氧杂苯酞。此外，通过使用 4-戊炔-1-醇（具有内部炔）作为环化配偶体，通过发散的 [2 + 3]-成环途径。
• B(C₆F₅)₃-Catalyzed Intramolecular Hydroalkoxylation Deuteration Reactions of Unactivated Alkynyl Alcohols
  作者：Jianbo Tang、Jian-Fei Bai、Jinfeng Zheng、Shuangshuang Li、Zhi-Jiang Jiang、Jia Chen、Kun Gao、Zhanghua Gao

  DOI：10.1021/acs.orglett.3c02592

  日期：2023.9.22

  D2O as a deuterium source, a method for the deuteration of intra- and extra-cyclic methylene has been developed for cyclic ethers with moderate yield and excellent deuterium incorporation. This transformation features superb functional group tolerance in a wide range of alkynols. Notably, the critical factor to achieve high deuterium incorporation is determined by the hydrogen isotope exchange reaction

  使用D 2 O作为氘源，开发了一种环内和环外亚甲基氘化方法，用于环醚，具有中等产率和优异的氘掺入性。这种转变在多种炔醇中具有极好的官能团耐受性。值得注意的是，实现高氘掺入的关键因素是由不稳定的氧鎓离子的氢同位素交换反应决定的。这种新颖的方法为许多用其他方法通常难以制备的有价值的氘代环醚提供了一种有效且简洁的合成路线。
• 10.1021/jacs.4c05136
  作者：Scaringi, Simone、Leforestier, Baptiste、Mazet, Clément

  DOI：10.1021/jacs.4c05136

  日期：——

  remote functionalizations based on alkene isomerization. In contrast, protocols based on alkyne isomerization are comparatively rare. Herein, we report a general Pd-catalyzed long-range isomerization of alkynyl alcohols. Starting from aryl-, heteroaryl-, or alkyl-substituted precursors, the optimized system provides access preferentially to the thermodynamically more stable α,β-unsaturated aldehydes

  近年来，基于烯烃异构化的远程官能化催化方法的开发取得了进展。相比之下，基于炔烃异构化的方案相对较少。在此，我们报道了一种通用的 Pd 催化的炔醇长程异构化方法。从芳基、杂芳基或烷基取代的前体开始，优化的系统优先提供热力学更稳定的α,β-不饱和醛，并且与潜在敏感的官能团相容。我们表明，碳-碳三键的两个 π 组分的迁移可以在几个亚甲基单元上持续。计算研究有助于阐明负责反应性和选择性的关键基本步骤。其中包括在最终互变异构事件中非正统的膦辅助去质子化而不是更传统的β-氢化物消除。
• Synthesis of cyclopentane-fused oxygen heterocycles from the intramolecular reaction of alkynes with cyclopropylcarbene-chromium complexes
  作者：James W. Herndon、Julius J. Matasi

  DOI：10.1021/jo00290a003

  日期：1990.2