4-烯丙基-1,2-二甲基苯 | 42918-23-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-烯丙基-1,2-二甲基苯
• 英文名称: 4-allyl-1,2-dimethylbenzene
• 英文别名: 3-(3,4-Dimethylphenyl)-1-propene；1,2-dimethyl-4-prop-2-enylbenzene
• CAS: 42918-23-0
• 化学式: C₁₁H₁₄
• 分子量: 146.232
• InChiKey: KBSAWXFUQFSLNB-UHFFFAOYSA-N

物化性质

• 熔点：
  268-275 °C
• 沸点：
  95-97 °C(Press: 20 Torr)
• 密度：
  0.878±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  4-烯丙基-1,2-二甲基苯 在 甲基磺酰胺 、 AD-mix β 、 对甲苯磺酸 作用下， 以 水 、 甲苯 、 叔丁醇 为溶剂， 反应 24.0h， 生成 5-(2-(4-(3,4-dimethylbenzyl)-1,3-dioxolan-2-yl)phenyl)pyrimidine
  参考文献：
  名称：

  Palladium-Catalyzed meta-C–H Olefination of Arene-Tethered Diols Directed by Well-Designed Pyrimidine-Based Group

  摘要：

  The palladium-catalyzed meta-olefination of arene-tethered diols attached to a well-designed pyrimidine moiety is presented. Applications of the protocol are illustrated by the synthesis of various diol-based natural products, such as coumarins, phenylpropanoids, stilbenes, and chalcones. Advantages of this method are demonstrated through the easy removal of the template and a gram-scale olefination reaction. Finally, experimental verification, including H-1 NMR, ESI-MS and IR, and DFT studies are undertaken to elucidate the mechanistic complexity.

  DOI：

  10.1021/acs.orglett.9b00433
• 作为产物：
  描述：

  烯丙基三甲氧基硅烷 、 邻甲基氯化苄 在 四(三苯基膦)钯 、 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.17h， 以79%的产率得到4-烯丙基-1,2-二甲基苯
  参考文献：
  名称：

  钯催化的sp 2 –sp 3氯甲基芳烃与烯丙基三甲氧基硅烷的偶联：烯丙基芳烃的合成

  摘要：

  这项工作描述了氯甲基芳烃与烯丙基三甲氧基硅烷的钯催化的远程sp 2 –sp 3偶联反应。烯丙基化反应区域选择性地发生在1-（氯甲基）萘和苄基氯的对位上，形成新的C（sp 2）–C（sp 3）键。反应在温和条件下平稳进行，以中等至极好的收率生产烯丙基芳烃。

  DOI：

  10.1021/acs.joc.7b00678
• 作为试剂：
  描述：

  [(2R,3R,4R,6R)-4-azido-6-(benzenesulfinyl)-3-triethylsilyloxyoxan-2-yl]methyl 3-methylbutanoate 、 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 、 4-烯丙基-1,2-二甲基苯 为溶剂， 以78%的产率得到C₆₆H₈₆N₆O₁₃SSi₂
  参考文献：
  名称：

  Design and synthesis of functionalized trisaccharides as p53-peptide mimics

  摘要：

  Oligosaccharides represent potentially useful scaffolds for the development of peptidomimetics. We report here the design and synthesis of functionalized trisaccharides modeled after an alpha-helical 15-mer peptide region of p53 which binds to its cellular regulator MDM2. The trisaccharide scaffold was obtained efficiently by applying the sulfoxide glycosylation reaction as a key methodology. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.012

文献信息

• Palladium-Catalyzed Regioselective Allylation of Chloromethyl(hetero)arenes with Allyl Pinacolborate
  作者：Sheng Zhang、Aziz Ullah、Yoshinori Yamamoto、Ming Bao

  DOI：10.1002/adsc.201700350

  日期：2017.8.17

  The palladium-catalyzed regioselective allylation reaction between chloromethyl(hetero)arenes and allyl pinacolborate is reported in this work. Chloromethylarenes smoothly reacted with allyl pinacolborate, producing para-allylated dearomatization products or para-allylated arenes in satisfactory to good yields. 2-(Chloromethyl)thiophenes and 2-(chloromethyl)furans bearing substituents on the 5-positions

  在这项工作中报道了氯甲基（杂）芳烃与频哪醇硼酸烯丙酯之间的钯催化的区域选择性烯丙基化反应。氯甲基芳烃与频哪醇硼酸烯丙基酯平稳反应，以令人满意的产率获得对芳基化的脱芳烃化产物或对芳基化的芳烃。在5-位带有取代基的2-（氯甲基）噻吩和2-（氯甲基）呋喃也与频哪醇硼酸烯丙酯平滑地反应，以令人满意的产率产生5-烯丙基化的脱芳香化产物。
• Aerobic Asymmetric Allylic C−H Alkylation by Synergistic Chiral Primary Amine‐Palladium‐Hydroquinone Catalysis
  作者：Rui Wang、Long Zhang、Sanzhong Luo

  DOI：10.1002/chem.202304316

  日期：2024.3.15

  A ternary and synergistic chiral primary amine/palladium /p-hydroquinone catalysis was developed to facilitate oxidative asymmetric allylic C−H alkylation under aerobic conditions with high regio- and enantioselectivity.

  开发了三元协同手性伯胺/钯/对氢醌催化，以促进有氧条件下的氧化不对称烯丙基 C−H 烷基化，具有高区域和对映选择性。
• Palladium-Catalyzed <i>meta</i>-C–H Olefination of Arene-Tethered Diols Directed by Well-Designed Pyrimidine-Based Group
  作者：Siqiang Fang、Xiaobing Wang、Fucheng Yin、Pei Cai、Huali Yang、Lingyi Kong

  DOI：10.1021/acs.orglett.9b00433

  日期：2019.3.15

  The palladium-catalyzed meta-olefination of arene-tethered diols attached to a well-designed pyrimidine moiety is presented. Applications of the protocol are illustrated by the synthesis of various diol-based natural products, such as coumarins, phenylpropanoids, stilbenes, and chalcones. Advantages of this method are demonstrated through the easy removal of the template and a gram-scale olefination reaction. Finally, experimental verification, including H-1 NMR, ESI-MS and IR, and DFT studies are undertaken to elucidate the mechanistic complexity.
• Palladium-Catalyzed sp²–sp³ Coupling of Chloromethylarenes with Allyltrimethoxysilane: Synthesis of Allyl Arenes
  作者：Sheng Zhang、Jinfang Cai、Yoshinori Yamamoto、Ming Bao

  DOI：10.1021/acs.joc.7b00678

  日期：2017.6.2

  Palladium-catalyzed remote sp2–sp3 coupling reaction of chloromethylarenes with allyltrimethoxysilane is described in this work. The allylation reaction regioselectively occurred on the para-positions of 1-(chloromethyl)naphthalenes and benzyl chlorides to form new C(sp2)–C(sp3) bonds. The reaction proceeds smoothly under mild conditions to produce allyl arenes in moderate to excellent yields.

  这项工作描述了氯甲基芳烃与烯丙基三甲氧基硅烷的钯催化的远程sp 2 –sp 3偶联反应。烯丙基化反应区域选择性地发生在1-（氯甲基）萘和苄基氯的对位上，形成新的C（sp 2）–C（sp 3）键。反应在温和条件下平稳进行，以中等至极好的收率生产烯丙基芳烃。