4-(1-hydroxybut-3-yn-yl)benzonitrile | 121598-69-4

• 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: 4-(1-hydroxybut-3-yn-yl)benzonitrile
• 英文别名: 4-(1-hydroxybut-3-yn-1-yl)benzonitrile；1-(4-cyano-phenyl)-but-3-yn-1-ol；4-(1-Hydroxybut-3-ynyl)benzonitrile
• CAS: 121598-69-4
• 化学式: C₁₁H₉NO
• 分子量: 171.199
• InChiKey: IQVZNUGJJXZUDA-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C
• 沸点：
  348.2±32.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(1-hydroxybut-3-yn-yl)benzonitrile 在 bis-triphenylphosphine-palladium(II) chloride 、 dipotassium peroxodisulfate 、 copper(l) iodide 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 四丁基氯化铵 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  使用可见光照射系统从均炔醇合成 α-丙二烯醛/酮

  摘要：

  发现了由K 2 S 2 O 8和可见光光氧化还原催化介导的可见光照射串联氧化芳基迁移/羰基形成反应。所提出的转化提供了以伴随羰基形成的1,4-芳基转移的区域选择性方式从容易获得的均炔醇衍生物直接获得重要的α-丙二烯醛/酮衍生物。操作简单和底物范围广泛表明该方法在合成高功能α-丙二烯醛/酮衍生物方面具有巨大潜力。

  DOI：

  10.1039/d3ob00664f
• 作为产物：
  描述：

  potassium trifluoro(propa-1,2-dien-1-yl)borate 、 4-氰基苯甲醛 在 tonsil clay 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以90%的产率得到4-(1-hydroxybut-3-yn-yl)benzonitrile
  参考文献：
  名称：

  Regioselective propargylation of aldehydes using potassium allenyltrifluoroborate promoted by tonsil

  摘要：

  The propargylation of aldehydes using potassium allenyltrifluoroborate promoted by tonsil, an inexpensive and readily available clay, in a chemo- and regioselective way is described. The method is simple and avoids the use of air and moisture sensitive organometallics and products were obtained in good to moderate yields. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.01.017

文献信息

• Preparation of Organoaluminum Reagents from Propargylic Bromides and Aluminum Activated by PbCl2 and Their Regio- and Diastereoselective Addition to Carbonyl Derivatives
  作者：Li-Na Guo、Hongjun Gao、Peter Mayer、Paul Knochel

  DOI：10.1002/chem.201000523

  日期：2010.8.23

  propargylic and allenic aluminum reagents have been easily prepared by a direct insertion of aluminum into propargylic bromides in the presence of PbCl2 (1 mol %). These organoaluminum reagents react with carbonyl compounds to afford the corresponding allenic alcohols or homopropargylic alcohols in good to excellent yields with high regio‐ and diastereoselectivity.

  通过在PbCl 2（1 mol％）存在下将铝直接插入到炔丙基溴中，可以很容易地制备出各种炔丙基和烯丙基铝试剂。这些有机铝试剂可与羰基化合物反应，以高至极高的选择性和高非对映选择性提供相应的烯丙醇或均丙炔醇。
• Rhodium(I)-Catalyzed Carbonyl Allenylation versus Propargylation via Redox Transmetalation Across Tetragonal Tin(II) Oxide
  作者：Moloy Banerjee、Sujit Roy

  DOI：10.1021/ol0493352

  日期：2004.6.1

  [reaction: see text] A reagent combination of beta-SnO and catalytic [Rh(COD)Cl](2) in THF-H(2)O promotes the reaction of propargyl bromides and aldehydes and directs the regioselectivity toward the formation of either allenic alcohols or homopropargylic alcohols. This highly regioselective either/or transformation proceeds via a transmetalation from rhodium to tin, in which metallotropic rearrangement

  [反应：参见文本]β-SnO和催化性[Rh（COD）Cl]（2）在THF-H（2）O中的试剂组合可促进炔丙基溴和醛的反应，并指导区域选择性的形成烯丙醇或均丙醇。这种高度区域选择性的或/或转变是通过从铑到锡的过渡金属化进行的，其中炔丙基金属和烯丙基金属之间的金属向重排被阻止。
• Palladium(0) catalyzed regioselective carbonyl propargylation across tetragonal tin(ii) oxide via redox transmetallationElectronic supplementary information (ESI) available: general method and experimental procedure and spectroscopic data for compounds 3–10. See http://www.rsc.org/suppdata/cc/b2/b211555g/
  作者：Moloy Banerjee、Sujit Roy

  DOI：10.1039/b211555g

  日期：2003.2.7

  Facile homopropargylation of aldehydes by propargyl bromides over tetragonal tin(II)oxide and catalytic palladium(0) occurs which is proposed to involve the prior formation of dinuclear allenylpalladium followed by redox transmetallation to β-SnO.

  四方二氧化锡（II）氧化物催化下，炔丙基溴与醛的便捷同向炔丙基化反应，被认为涉及先形成双核丙二烯基钯，随后通过氧化还原转金属化作用生成β-SnO。
• Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation
  作者：Jucleiton J R Freitas、Queila P S B Freitas、Silvia R C P Andrade、Juliano C R Freitas、Roberta A Oliveira、Paulo H Menezes

  DOI：10.3762/bjoc.16.19

  日期：——

  The propargylation of aldehydes promoted by microwave irradiation using allenylboron compounds in a chemo- and regioselective way is described. The corresponding products were obtained in short reaction time, high yield and purity without the need of any solvent when allenylboronic acid pinacol ester was used, or using a minimal amount of acetone when potassium allenyltrifluoroborate was used.

  描述了通过使用烯丙基硼化合物通过微波辐射以化学和区域选择性方式促进的醛的炔丙基化。当使用烯丙基硼酸频哪醇酯时，不需要任何溶剂，反应时间短，产率高，纯度高，而使用烯丙基三氟硼酸钾时，所使用的丙酮量少。
• One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping
  作者：Daichi Yamane、Haruna Tanaka、Akihiro Hirata、Yumiko Tamura、Daichi Takahashi、Yusuke Takahashi、Tohru Nagamitsu、Masaki Ohtawa

  DOI：10.1021/acs.orglett.1c00840

  日期：2021.4.2

  γ-lactonization of homopropargyl alcohols via an alkyne deprotonation/boronation/oxidation sequence has been developed. Oxidation of the generated alkynyl boronate affords the corresponding ketene intermediate, which is trapped by the adjacent hydroxy group to furnish the γ-lactone. We have optimized the conditions as well as examined the substrate scope and synthetic applications of this efficient one-pot

  已经开发了通过炔烃去质子化/硼化/氧化顺序的一锅法丙炔醇的γ-内酯化。氧化生成的炔基硼酸酯可得到相应的乙烯酮中间体，该中间体被相邻的羟基捕获，从而提供了γ-内酯。我们优化了条件，并研究了这种有效的一锅内酯化的底物范围和合成应用。