1-ethyl-4-(pent-4-en-1-ynyl)benzene | 1415029-91-2

• 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: 1-ethyl-4-(pent-4-en-1-ynyl)benzene
• 英文别名: 1-Ethyl-4-pent-4-en-1-ynylbenzene；1-ethyl-4-pent-4-en-1-ynylbenzene
• CAS: 1415029-91-2
• 化学式: C₁₃H₁₄
• 分子量: 170.254
• InChiKey: LXMYGAJZANOMNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4-羟基香豆素 、 1-ethyl-4-(pent-4-en-1-ynyl)benzene 在 四(三苯基膦)钯 、 苯甲酸 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以59 %的产率得到(E)-2-(4-ethylstyryl)-3,4-dihydro-2H,5H-pyrano[3,2-c]chromen-5-one
  参考文献：
  名称：

  Pd/布朗斯台德酸催化原子经济 [3 + 3] 4-羟基香豆素和跳过烯炔的环化

  摘要：

  我们报告了在钯/布朗斯台德酸催化下跳跃烯炔作为双亲电子试剂的前所未有的应用。跳跃烯炔与作为双亲核试剂的 4-羟基香豆素的 [3 + 3] 环化使得稠合 O-杂环的完全原子经济合成成为可能。该反应被认为是通过 Pd 催化的 C-H 活化跳过的烯炔产生二烯，随后通过 Pd 活化和 O-亲核攻击导致区域选择性形成六元杂环，其中乙烯基取代基。

  DOI：

  10.1021/acs.orglett.4c02215
• 作为产物：
  描述：

  乙酸烯丙酯 、 3-(4-乙基苯基)丙炔酸 在 Ni⁽¹⁺⁾*2C₂H₃O₂^(1-)*4H₂O 、 silver(I) acetate 、 1,4-双(二苯基膦)丁烷 、 锌 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以92%的产率得到1-ethyl-4-(pent-4-en-1-ynyl)benzene
  参考文献：
  名称：

  Nickel-catalyzed decarboxylative coupling reaction of alkynyl carboxylic acids and allyl acetates

  摘要：

  The coupling reaction of aryl alkynyl carboxylic acids and allyl acetates was carried out in the presence of nickel catalyst to produce the allyl alkynes in good yields. The optimized condition is that alkynyl carboxylic acid (1.0 equiv), allyl acetate (2.0 equiv), Ni(OAc)(2)center dot 4H(2)O (10 mol %), AgOAc (10 mol %), and zinc (1.0 equiv) were reacted at 100 degrees C for 0.5 h. In addition, when allyl alcohol was employed instead of allyl acetate, the desired product was obtained in good yield. In addition, when the reaction was carried out in the presence of base such as DBU and Cs2CO3, the allene compounds were formed in good yield. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.005

文献信息

• Nickel-catalyzed decarboxylative coupling reaction of alkynyl carboxylic acids and allyl acetates
  作者：Juseok Choe、Jiyoung Yang、Kyungho Park、Thiruvengadam Palani、Sunwoo Lee

  DOI：10.1016/j.tetlet.2012.10.005

  日期：2012.12

  The coupling reaction of aryl alkynyl carboxylic acids and allyl acetates was carried out in the presence of nickel catalyst to produce the allyl alkynes in good yields. The optimized condition is that alkynyl carboxylic acid (1.0 equiv), allyl acetate (2.0 equiv), Ni(OAc)(2)center dot 4H(2)O (10 mol %), AgOAc (10 mol %), and zinc (1.0 equiv) were reacted at 100 degrees C for 0.5 h. In addition, when allyl alcohol was employed instead of allyl acetate, the desired product was obtained in good yield. In addition, when the reaction was carried out in the presence of base such as DBU and Cs2CO3, the allene compounds were formed in good yield. (C) 2012 Elsevier Ltd. All rights reserved.
• 10.1021/acs.orglett.4c02215
  作者：Khaitan, Bhavya、Gandhi, Shikha

  DOI：10.1021/acs.orglett.4c02215

  日期：——

  We report an unprecedented application of skipped enynes as bis-electrophiles under palladium/Brønsted acid catalysis. A [3 + 3] annulation of skipped enynes with 4-hydroxy coumarins as bis-nucleophiles enables a completely atom-economic synthesis of fused O-heterocycles. The reaction is proposed to proceed via the Pd-catalyzed C–H activation of the skipped enyne leading to a diene, which upon subsequent

  我们报告了在钯/布朗斯台德酸催化下跳跃烯炔作为双亲电子试剂的前所未有的应用。跳跃烯炔与作为双亲核试剂的 4-羟基香豆素的 [3 + 3] 环化使得稠合 O-杂环的完全原子经济合成成为可能。该反应被认为是通过 Pd 催化的 C-H 活化跳过的烯炔产生二烯，随后通过 Pd 活化和 O-亲核攻击导致区域选择性形成六元杂环，其中乙烯基取代基。