1-(pent-4-en-1-ynyl)naphthalene | 1415029-96-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(pent-4-en-1-ynyl)naphthalene
• 英文别名: 1-Pent-4-en-1-ynylnaphthalene；1-pent-4-en-1-ynylnaphthalene
• CAS: 1415029-96-7
• 化学式: C₁₅H₁₂
• 分子量: 192.26
• InChiKey: DUZCQRWBVRLLED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  1,3-二氢-1-甲基-3-苯基-2H-吲哚-2-酮 、 1-(pent-4-en-1-ynyl)naphthalene 在 四(三苯基膦)钯 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以75.61%的产率得到
  参考文献：
  名称：

  通过钯催化的前烯基与烯炔的烯丙基烷基化反应获得1,3-二烯

  摘要：

  已经开发出前所未有的钯催化亲核试剂与未活化的跳过的炔烃的烯丙基烷基化反应。该方法无需直接安装离去基团或使用额外的氧化剂即可直接获得各种1,3-二烯。该反应显示出高原子经济性，良好的官能团耐受性，优异的区域选择性和可扩展性。用D 2 O作为助溶剂，可以高效地掺入氘。

  DOI：

  10.1021/acs.orglett.7b01960
• 作为产物：
  描述：

  乙酸烯丙酯 、 3-(1-萘基)-2-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88%的产率得到1-(pent-4-en-1-ynyl)naphthalene
  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

• Gold- or Indium-Catalyzed Cross-Coupling of Bromoalkynes with Allylsilanes through a Concealed Rearrangement
  作者：M. Elena de Orbe、Margherita Zanini、Ophélie Quinonero、Antonio M. Echavarren

  DOI：10.1021/acscatal.9b02314

  日期：2019.9.6

  The gold(I)-catalyzed reaction of bromoalkynes with allylsilanes gives 1,4-enynes in a formal cross-coupling reaction. Mechanistic studies revealed the involvement of gold(I) vinylidenes or vinylidenephenonium gold(I) cations depending on the substituent on the bromoalkyne. In the case of bromo arylalkynes, the vinylidenephenonium gold(I) cations lead to 1,4-enynes via a 1,2-aryl rearrangement. The same reactivity has been observed in the presence of InBr3.
• Accessing 1,3-Dienes via Palladium-Catalyzed Allylic Alkylation of Pronucleophiles with Skipped Enynes
  作者：Shang Gao、Hao Liu、Chi Yang、Zhiyuan Fu、Hequan Yao、Aijun Lin

  DOI：10.1021/acs.orglett.7b01960

  日期：2017.9.15

  An unprecedented palladium-catalyzed allylic alkylation of pronucleophiles with unactivated skipped enynes has been developed. This method provides a straightforward access to a wide array of 1,3-dienes without the need to preinstall leaving groups or employ extra oxidants. The reaction exhibited high atom economy, good functional group tolerance, excellent regioselectivities, and scalability. With

  已经开发出前所未有的钯催化亲核试剂与未活化的跳过的炔烃的烯丙基烷基化反应。该方法无需直接安装离去基团或使用额外的氧化剂即可直接获得各种1,3-二烯。该反应显示出高原子经济性，良好的官能团耐受性，优异的区域选择性和可扩展性。用D 2 O作为助溶剂，可以高效地掺入氘。
• 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.