methyl 4-(1-hydroxybut-3-ynyl)benzoate | 121598-68-3

• 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: methyl 4-(1-hydroxybut-3-ynyl)benzoate
• CAS: 121598-68-3
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: MPOMKPKUFYNLMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(1-hydroxybut-3-ynyl)benzoate 在 吡啶 、 三溴化磷 作用下， 生成 methyl 4-(1-bromo-3-butynyl)benzoate
  参考文献：
  名称：

  1,2,4-三嗪的分子内 Diels-Alder 反应。噻吩并[2,3- b ]吡啶的阮内镍脱硫合成3-烷基吡啶

  摘要：

  2-芳基-2,3-二氢噻吩并[2,3-b]吡啶是通过适当的3-取代1,2,4-三嗪中间体的分子内Diels-Alder反应制备的，然后用雷尼镍还原脱硫形成3-取代的吡啶。还描述了从氨基硫脲一锅法合成 2-芳基-2,3-二氢噻吩并[2,3-b]-吡啶。

  DOI：

  10.1016/j.tet.2021.132158
• 作为产物：
  描述：

  Methyl 4-(1-hydroxy-4-trimethylsilylbut-3-ynyl)benzoate 在 potassium carbonate 、 水 作用下， 以 甲醇 、 醋酸异丙酯 为溶剂， 反应 1.0h， 以1.98 g的产率得到methyl 4-(1-hydroxybut-3-ynyl)benzoate
  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

• 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。
• Highly efficient synthesis of propargyl- and allenyltitanium reagents from propargyl halides or propargyl alcohol derivatives. Practical synthesis of allenyl and homopropargyl alcohols
  作者：Takashi Nakagawa、Aleksandr Kasatkin、Fumie Sato

  DOI：10.1016/0040-4039(95)00514-d

  日期：1995.5

  Reaction of Ti(O-i-Pr)4/2 i-PrMgBr, synthetic equivalent of practical Ti(II) reagent, with propargyl halides or propargyl alcohol derivatives affords allenyl titanium compounds in excellent yields, thus providing an efficient and practical method for synthesis of both allenyl and homopropargyl alcohols by the successive treatment with aldehydes or ketones.

  的Ti的反应（OI-PR）4 /2 I-PrMgBr，实用的Ti（II）试剂的合成等价物，与炔卤或炔丙醇衍生物，得到丙二烯基的钛化合物以优良产率，从而提供一种有效的，实用的方法的合成烯醛和高炔丙醇均需通过醛或酮的连续处理。
• 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。
• Carbonyl propargylation or allenylation by 3-haloprop-1-yne with tin(ii) halides and tetrabutylammonium halides
  作者：Yoshiro Masuyama、Akihiro Ito、Mamiko Fukuzawa、Kohji Terada、Yasuhiko Kurusu

  DOI：10.1039/a806206d

  日期：——

  3-Bromoprop-1-yne causes carbonyl propargylation with tin(II) chloride and tetrabutylammonium bromide in water to produce 1-substituted but-3-yn-1-ols, while 3-chloroprop-1-yne causes carbonyl allenylation with tin(II) iodide and tetrabutylammonium iodide in 1,3-dimethylimidazolidin-2-one to produce 1-substituted buta-2,3-dien-1-ols.

  3-溴丙-1-炔在水中与氯化锡(II)和四正丁基溴化铵反应，导致羰基丙炔化，产生1-取代的丁-3-炔-1-醇；而3-氯丙-1-炔与碘化锡(II)和四正丁基碘化铵在1,3-二甲基咪唑烷-2-酮中反应，导致羰基烯丙化，产生1-取代的丁-2,3-二烯-1-醇。
• Gold-Catalyzed Oxidative Rearrangement of Homopropargylic Ether via Oxonium Ylide
  作者：Mei Xu、Tian-Tian Ren、Chuan-Ying Li

  DOI：10.1021/ol302238t

  日期：2012.9.21

  Synthetically useful α,β-unsaturated carbonyl compounds were obtained from gold-catalyzed oxidative rearrangement of homopropargylic ether under mild reaction conditions. Gold carbenoid and oxonium ylide are proposed as key intermediates.

  合成有用的α，β-不饱和羰基化合物是在温和的反应条件下，通过金催化的炔丙基醚的氧化重排而获得的。拟议中的金类胡萝卜素和叶立德是重要的中间体。