2-烯丙基-3-乙氧基-4-甲氧基苯甲醛 | 374073-49-1

• 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: 2-烯丙基-3-乙氧基-4-甲氧基苯甲醛
• 英文名称: 2-allyl-3-ethoxy-4-methoxybenzaldehyde
• 英文别名: 3-ethoxy-4-methoxy-2-prop-2-enylbenzaldehyde
• CAS: 374073-49-1
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: VUNRDSCEYVPEKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-烯丙基-3-乙氧基-4-甲氧基苯甲醛 在 copper dichloride 、 palladium dichloride 作用下， 以 水 为溶剂， 反应 1.0h， 以90%的产率得到5-ethoxy-6-methoxy-3-methylisocoumarin
  参考文献：
  名称：

  Pd(II)-Mediated Cyclization of o-Allylbenzaldehydes in Water: A Novel Synthesis of Isocoumarins

  摘要：

  A novel, concise and efficient synthesis of substituted isocoumarins is disclosed. o-Allylbenzaldehydes prepared from isovanillin were mediated by PdCl2-CuCl2 in water to undergo a domino reaction sequence, including 6-exo-trig cyclization, the addition of water, the elimination of PdHCl, the isomerization of carbon-carbon double bond, the oxidation of hemiacetals with the elimination of PdHCl, and regeneration of PdCl2 in situ to yield a series of new substituted isocoumarins in high yields, in one pot.

  DOI：

  10.1021/ol302256y
• 作为产物：
  描述：

  异香兰素 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 2-烯丙基-3-乙氧基-4-甲氧基苯甲醛
  参考文献：
  名称：

  由异香草醛通过克莱森重排和闭环复分解合成取代茚

  摘要：

  研究了取代茚的新合成方法。基于Claisen重排、Wittig反应和闭环复分解(RCM)，以异香草醛为原料合成了一系列取代茚，收率良好。

  DOI：

  10.1002/jccs.200400060

文献信息

• Synthesis of Substituted Indenes from Isovanillin via Claisen Rearrangement and Ring-Closing Metathesis
  作者：Keng-Shiang Huang、Eng-Chi Wang

  DOI：10.1002/jccs.200400060

  日期：2004.4

  A new synthesis of substituted indenes was studied. Based on Claisen rearrangement, Wittig reaction and ring-closing metathesis (RCM), a series of substituted indenes was synthesized from isovanillin in good yields.

  研究了取代茚的新合成方法。基于Claisen重排、Wittig反应和闭环复分解(RCM)，以异香草醛为原料合成了一系列取代茚，收率良好。
• Syntheses of Substituted Naphthalenes and Naphthols
  作者：Keng-Shiang Huang、Eng-Chi Wang、Hsing-Ming Chen

  DOI：10.1002/jccs.200400090

  日期：2004.6

  Syntheses of substituted naphthalenes and naphthols are described. Based on Claisen rearrangement, ring-closing metathesis (RCM), and related reactions, isovanillin was successfully transformed into a series of substituted naphthalenes and naphthols with good overall yields.

  描述了取代萘和萘酚的合成。基于克莱森重排、闭环复分解（RCM）和相关反应，异香草醛成功地转化为一系列具有良好总收率的取代萘和萘酚。
• Synthesis of Dibenzo-fused 10-Membered Cyclic Ethers from Isovanillin via Ring-closing Metathesis
  作者：Eng-Chi Wang、Yu-Li Lin、Hsing-Ming Chen、Sie-Rong Li、Chizuko Kabuto、Yoshio Takeuchi

  DOI：10.3987/com-05-10592

  日期：——

  A synthesis of substituted dibenzo-fused 10-membered cyclic ethers is described. 2-Allylbenzyl alcohols and 2-allylphenols derived from isovanillin were coupled by the Mitsunobu reaction to construct intramolecular dienes with ether linkage. The resulting dienes were subsequently treated with Grubbs' catalyst to undergo ring-closing metathesis to give the desired cyclic ethers.

  描述了取代二苯并稠合的 10 元环醚的合成。异香草醛衍生的2-烯丙基苄醇和2-烯丙基苯酚通过Mitsunobu反应偶联构建具有醚键的分子内二烯。随后用 Grubbs 催化剂处理所得二烯以进行闭环复分解以产生所需的环状醚。
• A novel synthesis of substituted naphthalenes via Claisen rearrangement and RCM reaction
  作者：Keng-Shiang Huang、Eng-Chi Wang

  DOI：10.1016/s0040-4039(01)01231-x

  日期：2001.8

  A novel synthesis of substituted naphthalenes was studied. Starting from isovanillin, basing on Claisen rearrangement and ring-closing metathesis (RCM), a series of 1-alkoxy-2-methoxynaphthalenes and 1-alkoxy-2-methoxy-8-methylnaphthalenes together with a series of 2-alkoxy-3-methoxynaphthalenes were synthesized.

  研究了取代萘的新型合成方法。从异香草醛开始，基于克莱森重排和闭环复分解（RCM），一系列1-烷氧基-2-甲氧基萘和1-烷氧基-2-甲氧基-8-甲基萘以及一系列2-烷氧基-3-合成了甲氧基萘。
• A Synthesis of Substituted 3,6-Dihydro-1H-benzo[c]oxocines via Claisen Rearrangement and Ring-closing Metathesis
  作者：Eng-Chi Wang、Chin-Cheng Wang、Ming-Kun Hsu、Keng-Shiang Huang

  DOI：10.3987/com-02-9560

  日期：——

  Started from isovanillin, based on Claisen rearrangement and ring-closing metathesis (RCM) reaction, a series of substituted 3,6-dihydro-1H-benzo[c]oxocines were synthesized in moderate yields.

  从异香草醛开始，基于克莱森重排和闭环复分解（RCM）反应，以中等收率合成了一系列取代的3,6-二氢-1H-苯并[c]氧辛烷。