2-phenylpent-4-yn-2-ol | 6712-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenylpent-4-yn-2-ol
• 英文别名: 2-phenyl-4-pentyn-2-ol
• CAS: 6712-35-2
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: PLUHTHABGAEVIL-UHFFFAOYSA-N

物化性质

• 沸点：
  77-79 °C(Press: 0.1 Torr)
• 密度：
  1.028 g/cm3(Temp: 23 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2906299090

反应信息

• 作为反应物：
  描述：

  2-phenylpent-4-yn-2-ol 以 乙醚 为溶剂， 生成 (Z)-6-Phenyl-hept-5-en-3-in-1-ol
  参考文献：
  名称：

  Quinkert,G. et al., Justus Liebigs Annalen der Chemie, 1971, vol. 748, p. 38 - 54

  摘要：

  DOI：
• 作为产物：
  描述：

  1-methyl-1-phenyl-4-(trimethylsilyl)-3-butyn-1-ol 在 potassium carbonate 、 水 作用下， 以 甲醇 、 醋酸异丙酯 为溶剂， 反应 1.0h， 以1.41 g的产率得到2-phenylpent-4-yn-2-ol
  参考文献：
  名称：

  Zinc Catalyzed and Mediated Propargylations with Propargyl Boronates

  摘要：

  The utility of allenyl and propargyl boronates for the propargylation of aldehydes and ketones mediated by zinc is presented. The reaction Is catalytic in zinc with allenyl or propargyl borolanes. The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed.

  DOI：

  10.1021/ol902457m

文献信息

• A Mechanochemical Zinc-Mediated Barbier-Type Allylation Reaction under Ball-Milling Conditions
  作者：JieXiang Yin、Roderick T. Stark、Ian A. Fallis、Duncan L. Browne

  DOI：10.1021/acs.joc.9b02876

  日期：2020.2.21

  A ball-milling-enabled zinc-mediated Barbier-type allylation reaction is reported. Notably, running the reaction in this manner renders it effective irrespective of the initial morphology of the zinc metal. The process is operationally simple, does not require inert atmospheres or dry solvents, and is reported over a range of aldehyde and ketone substrates; a gram-scale process is demonstrated.

  据报道有球磨功能的锌介导的Barbier型烯丙基化反应。值得注意的是，以这种方式进行反应使其有效，而与锌金属的初始形态无关。该方法操作简单，不需要惰性气氛或干燥溶剂，并且在一系列醛和酮底物上得到报道。演示了克级过程。
• Selective and Efficient Cycloisomerization of Alkynols Catalyzed by a New Ruthenium Complex with a Tetradentate Nitrogen-Phosphorus Mixed Ligand
  作者：Pei Nian Liu、Fu Hai Su、Ting Bin Wen、Herman H.-Y. Sung、Ian D. Williams、Guochen Jia

  DOI：10.1002/chem.200903441

  日期：——

  The new ruthenium complex [Ru(N3P)(OAc)][BPh4] (4), in which N3P is the N,P mixed tetradentate ligand N,N‐bis[(pyridin‐2‐yl)methyl]‐[2‐(diphenylphosphino)phenyl]methanamine was synthesized. The complex was found to be catalytically active for the endo cycloisomerization of alkynols. The catalytic reactions can be used to synthesize five‐, six‐, and seven‐membered endo‐cyclic enol ethers in good to

  新的钌络合物[Ru（N 3 P）（OAc）] [BPh 4 ]（4），其中N 3 P是N，P混合的四齿配体N，N-双[（吡啶-2-基）甲基合成了]-[2-（二苯基膦基）苯基]甲胺。复杂被认为是将催化活性的内炔醇环异构。催化反应可以用于合成的五元，六元，七元内以良好-环烯醇醚到优异的产率。提出了涉及亚乙烯基中间体的催化循环用于催化反应。用PhCCH和H 2 O处理配合物4，得到烷基配合物[Ru（CH2 Ph）（CO）（N 3 P）] [BPh 4 ]（30），这支持了以下假设：催化反应涉及在亚乙烯基配体的CC键上添加羟基。
• Re-engineering of PIP3-antagonist triazole PITENIN's chemical scaffold: development of novel antifungal leads
  作者：Sravani Pulya、Yadagiri Kommagalla、Duhita G. Sant、Shweta U. Jorwekar、Santosh G. Tupe、Mukund V. Deshpande、Chepuri V. Ramana

  DOI：10.1039/c5ra25145a

  日期：——

  A novel 4-(1-phenyl-1-hydroxyethyl)-1-(o-hydroxyphenyl)-1H-1,2,3-triazole was designed by integrating the structural features of triazole PITENIN anticancer agents and the azole class of antifungal drugs. A two-step protocol comprising the Barbier propargylation and Cu-catalyzed azide–alkyne cycloaddition was established to synthesise a diverse set of compounds of this class. Their screening against

  结合三唑PITENIN抗癌剂的结构特点和唑类抗真菌剂，设计了一种新型的4-（1-苯基-1-羟乙基）-1-（邻羟苯基）-1 H -1,2,3-三唑毒品。建立了包括Barbier炔丙基化和Cu催化的叠氮化物-炔烃环加成反应的两步方案，以合成各种此类化合物。他们对各种导致了几个潜在的抗真菌命中的识别和他们中的一些人真菌病原体筛查显示更好的抗真菌活性比对氟康唑光滑念珠菌，隐球菌，烟曲霉及黑曲霉。作用方式研究表明，它们的抗真菌活性是由于抑制羊毛甾醇14α-脱甲基酶（导致麦角固醇耗竭）或活性氧（ROS）产生。
• Synthesis of homopropargyl alcohols via sonochemical Barbier-type reaction
  作者：Adam Shih-Yuan Lee、Shu-Fang Chu、Yu-Ting Chang、Shu-Huei Wang

  DOI：10.1016/j.tetlet.2003.12.058

  日期：2004.2

  were synthesized from the reaction mixture of zinc powder, 1,2-diiodoethane, 3-bromo-1-propyne and aldehyde or ketone in anhydrous THF under ultrasound. The homopropargyl alcohols were obtained as the only product in all cases when aldehydes were reacted with 3-bromo-1-propyne under this sonochemical Barbier-type reaction condition. The homopropargyl alcohol was produced as the major product and the

  在超声波作用下，由锌粉，1,2-二碘乙烷，3-溴-1-丙炔和醛或酮在无水THF中的反应混合物合成了一系列高炔丙醇。当醛在这种声化学巴比尔型反应条件下与3-溴-1-丙炔反应时，在所有情况下均获得高炔丙醇作为唯一产物。当在反应条件下使用酮作为底物时，以高炔丙醇为主要产物，并且还获得了低污染的烯丙醇。
• Synthesis of Cyclopropanes via 1,3-Migration of Acyloxy Groups Triggered by Formation of α-Imino Rhodium Carbenes
  作者：Ze-Feng Xu、Jincheng Liu、Xin Chang、Tao Chen、Huaping Xu、Shengguo Duan、Chuan-Ying Li

  DOI：10.1021/acs.orglett.0c01764

  日期：2020.7.2

  A novel and highly efficient synthetic approach to cyclopropanes was realized via 1,3-migration of acyloxy groups triggered by α-imino rhodium carbenes. Excellent chemoselectivity ensured broad compatibility of common functional groups. Merits such as readily available substrates, mild reaction conditions, and time-saving processes qualified this transformation as an attractive alternative strategy

  通过α-亚氨基铑卡宾烯引发的酰氧基的1,3-迁移，实现了一种新型的高效合成环丙烷的方法。出色的化学选择性确保了常见官能团的广泛相容性。诸如易于获得的底物，温和的反应条件和省时的工艺等优点使这种转化成为合成多功能环丙烷的有吸引力的替代策略。介绍了对该机制的初步研究和讨论。