1-(4-chlorophenyl)-3-(p-tolyl)prop-2-yn-1-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(4-chlorophenyl)-3-(p-tolyl)prop-2-yn-1-ol
• 英文别名: 1-(4-chlorophenyl)-3-(4-methylphenyl)prop-2-yn-1-ol
• 化学式: C₁₆H₁₃ClO
• 分子量: 256.732
• InChiKey: QESPBSMXRQNYPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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-(4-chlorophenyl)-3-(p-tolyl)prop-2-yn-1-ol 在 吡啶 、 manganese(IV) oxide 、 sodium sulfate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 52.5h， 生成 (Z)-1-(4-chlorophenyl)-3-(p-tolyl)prop-2-yn-1-one O-methyl oxime
  参考文献：
  名称：

  Direct Synthesis of 4-Fluoroisoxazoles through Gold-Catalyzed Cascade Cyclization–Fluorination of 2-Alkynone O-Methyl Oximes

  摘要：

  A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl mimes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol % of (IPr)AuCl, 5 mol % of AgOTs, 2.5 equiv of Selectfluor, and 2 equiv of NaHCO3. This process features an efficient one-pot cascade route to fluoroisoxazoles with high yields and high selectivity under mild reaction conditions.

  DOI：

  10.1021/jo5008702
• 作为产物：
  描述：

  4-氯苯甲醛 、 4-甲苯基乙炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以95%的产率得到1-(4-chlorophenyl)-3-(p-tolyl)prop-2-yn-1-ol
  参考文献：
  名称：

  Direct Synthesis of 4-Fluoroisoxazoles through Gold-Catalyzed Cascade Cyclization–Fluorination of 2-Alkynone O-Methyl Oximes

  摘要：

  A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl mimes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol % of (IPr)AuCl, 5 mol % of AgOTs, 2.5 equiv of Selectfluor, and 2 equiv of NaHCO3. This process features an efficient one-pot cascade route to fluoroisoxazoles with high yields and high selectivity under mild reaction conditions.

  DOI：

  10.1021/jo5008702

文献信息

• Catalyst‐Controlled Dual Reactivity of Sulfonimidamides: Synthesis of Propargylamines and <i>N</i> ‐Propargyl Sulfonimidamides
  作者：Irfana Jesin C. P.、Ganesh Chandra Nandi

  DOI：10.1002/chem.201805000

  日期：2019.1.14

  amines and nucleophiles depending on the reaction conditions to access propargylamines and N‐propargyl SIAs, respectively. The amine part of SIAs has been cleaved in an InCl3‐catalyzed three‐component A3 coupling reaction with aldehyde and acetylene to yield propargylamine. Moreover, N‐propargyl SIAs were obtained via the direct‐imination of propargyl alcohols in the presence of BF3⋅OEt2.

  磺酰亚胺酰胺（SIA）既可以充当替代胺，又可以充当亲核试剂，具体取决于分别访问炔丙基胺和N炔丙基SIA的反应条件。SIAs的胺部分已在InCl 3催化的三组分A 3与醛和乙炔的偶联反应中裂解，生成炔丙基胺。此外，Ñ通过在BF的存在炔丙基醇的直接亚胺化得到-propargyl补充免疫3 ⋅OEt 2。
• Boron Trihalide Mediated Substitution of Hydroxyl Groups with Alkenyl, Alkynyl, and Allyl Moieties
  作者：George Kabalka、Scott Borella、Min-Liang Yao

  DOI：10.1055/s-2007-990816

  日期：2008.1

  The coupling of alcohols with alkenyl- and alkynylboron dihalides with high olefin stereoselectivity is described. The reaction provides a facile route to internal acetylenes. Notably, the allylation of propargylic alcohols mediated by boron trichloride proceeds smoothly at room temperature and gives excellent regioselectivity.

  描述了具有高烯烃立体选择性的醇与烯基和炔基硼二卤化物的偶联。该反应为内部乙炔提供了一条简便的途径。值得注意的是，由三氯化硼介导的炔丙醇的烯丙基化反应在室温下顺利进行，并具有优异的区域选择性。
• In Situ Generation of Allenes and their Application to One‐Pot Assembly of Functionalized Fluoreno[3,2‐ <i>b</i> ]furans by Calcium‐Catalyzed, Regioselective, 3‐Component Reactions
  作者：Srinivasarao Yaragorla、Pallava Rajesh

  DOI：10.1002/ejoc.202001310

  日期：2020.12.13

  A novel synthetic methodology for the synthesis of tetra‐annulated fluorenofurans and fluorenopyrans using calcium(II)‐catalyzed one‐pot, three‐component reaction is developed from propargyl alcohols and 1,3‐dicarbonyls through the formation of tetra‐substituted allenes as the key intermediates.

  由炔丙基醇和1,3-二羰基化合物通过形成四取代的丙烯作为炔烃，开发了一种新的合成方法，该方法由钙（II）催化的一锅三组分反应合成四氟呋喃和氟吡喃。关键中间体。
• <i>p</i>-TSA/Base-Promoted Propargylation/Cyclization of β-Ketothioamides for the Regioselective Synthesis of Highly Substituted (Hydro)thiophenes
  作者：Ganesh Chandra Nandi、Maya Shankar Singh

  DOI：10.1021/acs.joc.6b00342

  日期：2016.7.15

  achieved at room temperature. In addition, the reaction also provided thiazole rings as byproducts. Furthermore, the propargylated thioamides undergo intramolecular 1,5-cyclization to afford fully substituted (hydro)thiophenes in the presence of base. Notably, the approach is pot, atom, and step economical (PASE).

  在室温下，已实现了无金属的对甲苯磺酸（p -TSA）介导的β-酮硫代酰胺与芳基炔丙醇的直接炔丙基化。另外，该反应还提供了噻唑环作为副产物。此外，在碱的存在下，炔丙基化的硫代酰胺经过分子内的1，5-环化以提供完全取代的（氢）噻吩。值得注意的是，这种方法是锅，原子和阶梯式经济的（PASE）。
• Catalyst-Controlled Straightforward Synthesis of Highly Substituted Pyrroles/Furans via Propargylation/Cycloisomerization of α-Oxoketene-N,S-acetals
  作者：Ganesh Chandra Nandi、Soumini K

  DOI：10.1021/acs.joc.6b02367

  日期：2016.12.2

  A facile and efficient InCl3 catalyzed one-pot synthesis of highly substituted pyrroles has been developed via a tandem propargylation/cycloisomerization reaction of α-oxoketene-N,S-acetals with propargyl alcohols. Notably, in the presence of Bronsted acid p-TSA·H2O, the reaction afforded the hydrolyzed product propargylated-1,3-dicarbonyl compounds, which upon treatment with Cs2CO3 underwent regioselective

  通过α-氧杂环丁烯-N，S-乙缩醛与炔丙醇的串联炔丙基化/环异构化反应，已经开发出一种简便高效的InCl 3催化一锅合成高取代的吡咯。值得注意的是，在布朗斯台德酸对-TSA·H 2 O的存在下，反应提供了水解产物炔丙基化的1，3-二羰基化合物，其在用Cs 2 CO 3处理后进行了区域选择性的分子内环化，从而提供了四取代的呋喃衍生物。