4-甲氧基-2-(2-甲基-1-丙烯基)苯甲醛 | 610312-60-2

• 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-甲氧基-2-(2-甲基-1-丙烯基)苯甲醛
• 英文名称: 4-methoxy-2-(2-methyl-1-propenyl)benzencarbaldehyde
• 英文别名: 4-methoxy-2-(2-methylprop-1-en-1-yl)benzaldehyde；4-Methoxy-2-(2-methylprop-1-enyl)benzaldehyde
• CAS: 610312-60-2
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: WNYQNIXYOBNYOO-UHFFFAOYSA-N

物化性质

• 沸点：
  322.1±30.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-甲氧基-2-(2-甲基-1-丙烯基)苯甲醛 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 1-(4-甲氧基-2-(2-甲基丙-1-烯基)苯基)-丙-2-炔-1-醇
  参考文献：
  名称：

  Metal-Catalyzed Cycloisomerization of Enyne Functionalities via a 1,3-Alkylidene Migration

  摘要：

  We report a new metal-catalyzed 6-endo-dig cyclization of cis-4,6-dien-1-yn-3-ols, which produces substituted benzene and naphthalene derivatives with structural reorganization. In this process, we observe a 1,3-alkylidene migration via cleavage of the olefin double bond of the starting substrates. The ease and reliability of this cyclization are manifested by its compatibility with a wide array of diverse substrates and several pi-alkyne activators, including PtCl2, Zn(OTf)2, AuCl, and AuCl3.

  DOI：

  10.1021/ja062515h
• 作为产物：
  描述：

  3-甲氧基苯甲醛 在 正丁基锂 、 溴 作用下， 以 四氢呋喃 、 正己烷 、 溶剂黄146 为溶剂， 反应 24.5h， 生成 4-甲氧基-2-(2-甲基-1-丙烯基)苯甲醛
  参考文献：
  名称：

  Metal-Catalyzed Cycloisomerization of Enyne Functionalities via a 1,3-Alkylidene Migration

  摘要：

  We report a new metal-catalyzed 6-endo-dig cyclization of cis-4,6-dien-1-yn-3-ols, which produces substituted benzene and naphthalene derivatives with structural reorganization. In this process, we observe a 1,3-alkylidene migration via cleavage of the olefin double bond of the starting substrates. The ease and reliability of this cyclization are manifested by its compatibility with a wide array of diverse substrates and several pi-alkyne activators, including PtCl2, Zn(OTf)2, AuCl, and AuCl3.

  DOI：

  10.1021/ja062515h

文献信息

• Toward Homogeneous Brønsted-Acid-Catalyzed Intramolecular Carbonyl–Olefin Metathesis Reactions
  作者：Tuong Anh To、Binh Khanh Mai、Thanh Vinh Nguyen

  DOI：10.1021/acs.orglett.2c03099

  日期：2022.10.7

  The carbonyl–olefin metathesis (COM) reaction is an attractive approach for the formation of a new carbon–carbon double bond from a carbonyl precursor. In principle, this reaction can be promoted by the activation of the carbonyl group with a Brønsted acid catalyst; however, it is often complicated as a result of unwanted side reactions under acidic conditions. Thus, there have been only a very few

  羰基-烯烃复分解 (COM) 反应是从羰基前体形成新的碳-碳双键的一种有吸引力的方法。原则上，该反应可以通过用布朗斯台德酸催化剂活化羰基来促进；然而，由于在酸性条件下发生不希望的副反应，它通常很复杂。因此，只有极少数的布朗斯台德酸催化 COM 反应的例子，所有这些都需要专门设计的装置。在此，我们报告了一种新的实用均相布朗斯台德酸催化方案，该方案使用硝基甲烷（一种容易获得的溶剂）来促进分子内闭环 COM 反应。
• The role of oxygen acidity on the side-chain fragmentation of ring methoxylated benzocycloalkenol radical cations
  作者：Monica Bellanova、Massimo Bietti、Michela Salamone

  DOI：10.1016/s0040-4039(03)01620-4

  日期：2003.8

  The reactivity of 2,2-dimethyl-5-methoxyindan-1-ol (1) and 2,2-dimethyl-6-methoxytetral-2-ol (2) radical cations has been studied both in acidic and basic solution. At pH less than or equal to 4 both 1(.+) and 2(.+) undergo C-alpha-H deprotonation as the exclusive reaction with k = 4.6 x 10(4) and 3.2 x 10(4) s(-1), respectively. In basic solution 1(.+) and 2(.+) behave as oxygen acids undergoing -OH-induced alpha-OH deprotonation in a diffusion controlled process (k(-OH) approximate to 10(10) M-1 s(-1)). An intermediate alkoxyl radical is formed which undergoes a 1,2-hydrogen atom shift in competition with C-C beta-scission (with 1(.+)) or as the exclusive pathway (with 2(.+)). A behavior which is interpreted in terms of the greater ease of ring-opening of a five membered ring as compared to a six-membered one. (C) 2003 Elsevier Ltd. All rights reserved.