1-(buta-2,3-dien-1-yl)-3-methoxybenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(buta-2,3-dien-1-yl)-3-methoxybenzene
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: GIFMKPLMWQMJMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(buta-2,3-dien-1-yl)-3-methoxybenzene 、 异丁酸 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 potassium tert-butylate 、 C₄₈H₅₆FeO₂P₂ 作用下， 以 1,2-二氯乙烷 、 间二甲苯 为溶剂， 反应 24.0h， 以66%的产率得到
  参考文献：
  名称：

  钌催化的羧酸对艾伦烯的对映选择性加成

  摘要：

  报道了一种通过将羧酸加成到丙二烯上来合成支链烯丙酯的钌催化合成方法。基于 Josiphos 骨架设计和制备配体，反应产率高达 95%，对映体过量率高达 >99%。进行了氘标记实验并提出了合理的机制。五元环和六元环的对映体纯内酯是通过支链烯丙基酯产物的 RCM 反应合成的。

  DOI：

  10.1021/acscatal.1c03306

文献信息

• Co(III)-Catalyzed [4+1] Annulation of Amides with Allenes via C−H Activation
  作者：Ramadoss Boobalan、Rajagopal Santhoshkumar、Chien-Hong Cheng

  DOI：10.1002/adsc.201801335

  日期：2019.3.5

  Co(III)‐catalyzed [4+1] annulation of amides with allenes to synthesize isoindolone and 1,5‐dihydro‐pyrrol‐2‐one derivatives is reported. A wide range of aromatic and vinylic amides react with allenes to give the corresponding annulation products in good to excellent yields. The mechanistic studies strongly support that the catalytic reaction proceeds through an amide‐directed C−H activation, followed

  据报道，Co（III）催化酰胺与烯丙基的[4 + 1]环合反应合成异吲哚酮和1,5-二氢吡咯-2-酮衍生物。各种各样的芳族和乙烯基酰胺与烯类反应，以良好或优异的收率得到相应的环状产物。机理研究强烈支持催化反应通过酰胺导向的CH活化，随后的丙二烯碳钴化，β-氢化物消除和分子内1,2-氨基胺化来进行。
• Synthesis of 1,2-Dihydroquinolines by Co(III)-Catalyzed [3 + 3] Annulation of Anilides with Benzylallenes
  作者：Ramajayam Kuppusamy、Rajagopal Santhoshkumar、Ramadoss Boobalan、Hsin-Ru Wu、Chien-Hong Cheng

  DOI：10.1021/acscatal.7b04087

  日期：2018.3.2

  A cobalt-catalyzed C–H/N–H annulation of anilides with allenes to synthesize 1,2-dihydroquinolines is described. The reaction proceeds via a C–H activation, allene insertion, followed by β-hydride elimination and an intramolecular 1,4-addition to a butadiene-group-containing intermediate. Allenes act as a three-carbon source in the present C–H activation strategy.

  描述了钴催化的丙二醛与丙二烯的CH-NH / NH环合反应，以合成1,2-二氢喹啉。该反应通过C–H活化，丙二烯插入，随后的β-氢化物消除和分子内1，4-加成至含丁二烯基团的中间体而进行。在当前的C–H活化策略中，丙二烯可作为三碳源。
• Direct synthesis of indazole derivatives <i>via</i> Rh(<scp>iii</scp>)-catalyzed C–H activation of phthalazinones and allenes
  作者：Chuanliu Yin、Tianshuo Zhong、Xiangyun Zheng、Lianghao Li、Jian Zhou、Chuanming Yu

  DOI：10.1039/d1ob01458g

  日期：——

  A novel Rh(III)-catalyzed annulation of phthalazinones or pyridazinones with various allenes was developed, leading to the formation of indazole derivatives bearing a quaternary carbon in moderate to good yields. The targeted products were synthesized via sequential C–H activation and olefin insertion, followed by β-hydride elimination and intramolecular cyclization. The synthetic protocol proceeded

  开发了一种新型 Rh( III ) 催化的酞嗪酮或哒嗪酮与各种丙二烯的环化反应，从而以中等至良好的产率形成带有季碳的吲唑衍生物。目标产物通过连续的C-H活化和烯烃插入，然后是β-氢化物消除和分子内环化来合成。合成方案有效地进行，具有广泛的官能团耐受性、高原子效率和高Z选择性。通过合成转化证明了该方法的实用性。
• Asymmetric Alkenyl C−H Functionalization by Cp ^x Rh ^III forms 2 <i>H</i> ‐Pyrrol‐2‐ones through [4+1]‐Annulation of Acryl Amides and Allenes
  作者：Shou‐Guo Wang、Yang Liu、Nicolai Cramer

  DOI：10.1002/anie.201909971

  日期：2019.12.9

  AbstractAn efficient CpxRhIII‐catalyzed enantioselective alkenyl C−H functionalization/[4+1] annulation of acryl amides and allenes is reported. The described transformation provides straightforward access to enantioenriched α,β‐unsaturated‐γ‐lactams bearing a quaternary stereocenter. The reaction operates under mild conditions, displays a broad functional‐group tolerance, and provides 2H‐pyrrol‐2‐ones with excellent selectivity of up to 97:3 er. Such scaffolds are frequently found in natural products and synthetic bioactive compounds and are of significant synthetic value. It is noteworthy that the allene serves as a one‐carbon unit in the [4+1]‐annulation.
• Ruthenium-Catalyzed Enantioselective Addition of Carboxylic Acids to Allenes
  作者：Jiang-Lin Hu、Felix Bauer、Bernhard Breit

  DOI：10.1021/acscatal.1c03306

  日期：2021.10.1

  A ruthenium-catalyzed synthetic method for branched allylic esters via addition of carboxylic acids to allenes is reported. Ligands were designed and prepared based on the Josiphos skeleton, with which the reaction achieved up to 95% yield and up to >99% enantiomeric excess. A deuterium labeling experiment was performed and a plausible mechanism was proposed. Enantiopure lactones of five- and six-membered

  报道了一种通过将羧酸加成到丙二烯上来合成支链烯丙酯的钌催化合成方法。基于 Josiphos 骨架设计和制备配体，反应产率高达 95%，对映体过量率高达 >99%。进行了氘标记实验并提出了合理的机制。五元环和六元环的对映体纯内酯是通过支链烯丙基酯产物的 RCM 反应合成的。