1-tert-butyl-4-(pent-4-en-1-ynyl)benzene | 1415029-92-3

• 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: 1-tert-butyl-4-(pent-4-en-1-ynyl)benzene
• 英文别名: 1-(tert-butyl)-4-(pent-4-en-1-yn-1-yl)benzene；1-Tert-butyl-4-pent-4-en-1-ynylbenzene；1-tert-butyl-4-pent-4-en-1-ynylbenzene
• CAS: 1415029-92-3
• 化学式: C₁₅H₁₈
• 分子量: 198.308
• InChiKey: LEHLRBYIZVMFLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  6-氯-4-羟基香豆素 、 1-tert-butyl-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52 %的产率得到(E)-2-(4-(tert-butyl)styryl)-9-chloro-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-(tert-butyl)phenyl)propiolic acid 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95%的产率得到1-tert-butyl-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

• Preparation of Solid Polyfunctional Alkynylzinc Pivalates with Enhanced Air and Moisture Stability for Organic Synthesis
  作者：Yi-Hung Chen、Carl Phillip Tüllmann、Mario Ellwart、Paul Knochel

  DOI：10.1002/anie.201704400

  日期：2017.7.24

  We report the preparation of solid and air‐stable polyfunctionalized alkynylzinc pivalates from the corresponding alkynes using TMPZnOPiv (TMP=2,2,6,6‐tetramethylpiperidyl) as base. These organozinc pivalates are obtained as powders under mild conditions in excellent yields and can be manipulated in air for several hours without significant decomposition. These zinc reagents show an excellent reactivity

  我们报告了使用TMPZnOPiv（TMP = 2,2,6,6-四甲基哌啶基）为基础从相应的炔烃制备固体和空气稳定的多官能炔基锌新戊酸酯。这些有机新戊酸酯在温和的条件下以粉末形式以优异的收率获得，并且可以在空气中操作数小时而不会发生明显的分解。这些锌试剂在各种碳-碳键形成反应和1,3-偶极环加成反应中显示出极好的反应性。新戊酸炔基锌已用于制备具有潜在抗肿瘤活性的羧酰胺基三唑，其分八步进行，总收率为38％。
• Asymmetric α-Allylation of Aldehydes with Alkynes by Integrating Chiral Hydridopalladium and Enamine Catalysis
  作者：Yong-Liang Su、Lu-Lu Li、Xiao-Le Zhou、Zhen-Yao Dai、Pu-Sheng Wang、Liu-Zhu Gong

  DOI：10.1021/acs.orglett.8b00740

  日期：2018.4.20

  A palladium-catalyzed asymmetric α-allylation of aldehydes with alkynes has been established by integrating the catalysis of enamine and chiral hydridopalladium complex that is reversibly formed from the oxidative addition of Pd(0) to chiral phosphoric acid. The ternary catalyst system, consisting of an achiral palladium complex, a primary amine, and a chiral phosphoric acid allows the reaction to

  通过整合烯胺和手性氢化钯配合物的催化作用，建立了钯与炔烃的醛催化不对称α-烯丙基化反应，该催化作用是将Pd（0）氧化添加到手性磷酸中而可逆地形成的。由非手性钯配合物，伯胺和手性磷酸组成的三元催化剂体系使反应可耐受各种α，α-二取代的醛和炔烃，从而以高收率和优异的收率提供了相应的烯丙基化产物对映选择性水平。
• 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.
• 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。