2-methyl-4-phenylbut-3-yn-1-ol | 17075-00-2

• 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-methyl-4-phenylbut-3-yn-1-ol
• CAS: 17075-00-2
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: QDZSJVRDDGAUMB-UHFFFAOYSA-N

物化性质

• 沸点：
  279.5±23.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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

反应信息

• 作为反应物：
  描述：

  2-methyl-4-phenylbut-3-yn-1-ol 在 chromium(VI) oxide 、 草酰氯 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 2-Methyl-4-phenyl-3-butynoylchlorid
  参考文献：
  名称：

  A comparison of allylic and proparglyic radicals

  摘要：

  DOI：

  10.1021/ja00991a018
• 作为产物：
  描述：

  2-methyl-2-(2-phenylethynyl)oxirane 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 2-methyl-4-phenylbut-3-yn-1-ol
  参考文献：
  名称：

  钯 (II) 催化的双取代炔烃的区域选择性合成氢芳基化反应，使用可移除的导向基团

  摘要：

  已经开发了钯 (II) 催化的高炔丙基胺的区域选择性顺氢芳基化反应，其中选择性由可裂解的双齿导向基团控制。在优化的反应条件下，发现二烷基和烷芳基炔底物均以高选择性进行加氢芳基化。该反应的产物含有 4,4-二取代的高烯丙基胺基序，这在药物分子和其他生物活性化合物中很常见。

  DOI：

  10.1021/jacs.6b08818

文献信息

• Csp–Csp³ Bond Formation via Iron(III)-Promoted Hydroalkynylation of Unactivated Alkenes
  作者：Yangyong Shen、Bo Huang、Jing Zheng、Chen Lin、Yu Liu、Sunliang Cui

  DOI：10.1021/acs.orglett.7b00499

  日期：2017.4.7

  An iron(III)-promoted hydroalkynylation of unactivated alkenes toward Csp–Csp3 bond formation has been developed. Various alkenes, including mono-, di-, and trisubstituted alkenes, could all smoothly convert to structural diversified alkynes in this chemoselective protocol. Additionally, the scalability was unraveled and the further divergent transformations of products were conducted to demonstrate

  已开发出铁（III）促进未活化烯烃向Csp–Csp 3键形成的加氢烷基化反应。在这种化学选择性方案中，各种烯烃，包括单，二和三取代的烯烃，都可以平稳地转化为结构多样化的炔烃。此外，还没有对可扩展性进行说明，并且对产品进行了进一步多样化的转换以证明其综合实用性。
• Palladium-catalysed preparation of 1,2-dienes by selective hydrogenolysis of alk-2-ynyl carbonates with ammonium formate
  作者：Jiro Tsuji、Teruo Sugiura、Masami Yuhara、Ichiro Minami

  DOI：10.1039/c39860000922

  日期：——

  1,2-Dienes were prepared by the selective hydrogenolysis of alk-2-ynyl carbonates with HCO2NH4 catalysed by Pd2(dba)3·CHCl3–PBun3(dba = dibenzylideneacetone).

  通过由Pd 2（dba）3 ·CHCl 3 -PBu n 3（dba =二苄叉基丙酮）催化的HCO 2 NH 4选择性催化碳酸氢-2-烷基酯与碳酸2-2-炔酯制备1,2-二烯。
• 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。
• Metal-free Hydroalkoxylation-Formal [4+2] Cycloaddition Cascade for the Synthesis of Ketals
  作者：Santosh J. Gharpure、Santosh K. Nanda、Padmaja、Yogesh G. Shelke

  DOI：10.1002/chem.201701659

  日期：2017.7.26

  A transition metal free, acid promoted cascade hydroalkoxylation–formal [4+2] cycloaddition of various alkynols with salicylaldehyde is demonstrated for the synthesis of tetrahydrofurano/pyrano‐chromenes and spiroketals. In general, alkynols underwent hydroalkoxylations in an endo‐dig manner when internal alkynes were used to furnish the heteroannular ketals, whereas terminal alkynes proceeded in an

  证明了无过渡金属，酸促进的各种炔醇与水杨醛的级联加氢烷氧基化–正式[4 + 2]环加成反应可合成四氢呋喃/吡喃-铬酮和螺酮。一般来说，炔醇经历在hydroalkoxylations内切-挖方式时内部炔烃被用来提供所述heteroannular缩酮，而末端炔烃在进行外切-挖引领潮流的时尚。研究表明，当偶合伙伴是水杨醛时，炔醇的分子内加氢烷氧基化是生成氧鎓离子的首选途径。这种无金属的转化为快速选择性地合成四氢呋喃呋喃和吡喃铬酮提供了新的途径。
• Relative Asymmetric Induction in the Intramolecular Reaction between Alkynes and Cyclopropylcarbene−Chromium Complexes:  Stereocontrolled Synthesis of Five-Membered Rings Fused to Oxygen Heterocycles
  作者：Jingbo Yan、Jin Zhu、Julius J. Matasi、James W. Herndon

  DOI：10.1021/jo982144q

  日期：1999.2.1

  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.