2-hydroxy-3-methoxycinnamaldehyde | 333754-89-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-hydroxy-3-methoxycinnamaldehyde
• 英文别名: 3-(2-Hydroxy-3-methoxyphenyl)-2-propenal；3-(2-hydroxy-3-methoxyphenyl)prop-2-enal
• CAS: 333754-89-5
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: IEYOVTKXZDUOOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-methoxycinnamaldehyde 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 30.0h， 生成 dimethyl 2-((4R)-3,4-dihydro-8-methoxy-2H-chromen-4-yl)malonate
  参考文献：
  名称：

  丙二酸酯与邻羟基肉桂醛的高对映选择性共轭加成-级联反应：4-取代色酚的不对称合成

  摘要：

  丙二酸酯与邻羟基肉桂醛的不对称有机催化共轭加成-环化反应可生成4-取代的chroman-2-ols，已使用二苯基脯氨醇三甲基甲硅烷基（TMS）醚作为有机催化剂。获得所需产物，具有良好至优异的产率和高对映选择性（高达> 99％ee）。在后续反应后形成了合成上有用的苯并二氢吡喃衍生物。

  DOI：

  10.1002/adsc.201100324
• 作为产物：
  描述：

  邻香草醛 、 甲酰甲撑基三苯基磷 以 苯 为溶剂， 反应 7.0h， 生成 2-hydroxy-3-methoxycinnamaldehyde
  参考文献：
  名称：

  An Efficient Carbene-Catalyzed Access to 3,4-Dihydrocoumarins

  摘要：

  Dihydrocoumarins play an important role as flavor and fragrance compounds and can be prepared efficiently from o-hydroxycinnamaldehydes in a mild, atom-economic N-heterocyclic carbene-catalyzed redox lactonization. Corresponding coumarins are accessible via a one-pot domino oxidation lactonization procedure in the presence of oxidants.

  DOI：

  10.1021/jo802285r

文献信息

• Synthesis of Chiral Polycyclic Tetrahydrocarbazoles by Enantioselective Aminocatalytic Double Activation of 2-Hydroxycinnamaldehydes with Dienals
  作者：Yong-Chao Ming、Xue-Jiao Lv、Ming Liu、Yan-Kai Liu

  DOI：10.1021/acs.orglett.1c02309

  日期：2021.8.20

  An efficient aminocatalytic enantioselective double-activation strategy has been developed that combines several different aminocatalytic modes in a cascade process, such as iminium ion, vinylogous iminium ion, trienamine, and dienamine activations. By using this strategy, 2-hydroxycinnamaldehydes worked well with various dienals via [4 + 2] cycloaddition and the oxa-Michael reaction-initiated cascade

  已经开发了一种有效的氨基催化对映选择性双活化策略，它在级联过程中结合了几种不同的氨基催化模式，例如亚胺离子、乙烯基亚胺离子、三烯胺和二烯胺活化。通过使用这种策略，2-羟基肉桂醛分别通过 [4 + 2] 环加成和 oxa-Michael 反应引发的级联与各种二烯很好地配合，从而产生具有优异非对映选择性和对映选择性的手性多环四氢咔唑和色满衍生物。
• Asymmetric synthesis of drug-like spiro[chroman-3,3′-indolin]-2′-ones through aminal-catalysis
  作者：Dhevalapally B. Ramachary、M. Shiva Prasad、S. Vijaya Laxmi、R. Madhavachary

  DOI：10.1039/c3ob42100g

  日期：——

  Asymmetric synthesis of drug-like functionalized spiro[chroman-3,3′-indolin]-2′-ones 5 containing three contiguous stereocenters with high diastereo- and enantioselectivities was achieved using the reflexive-Michael (r-M) reaction of unmodified hydroxyenals 1 with various (E)-3-alkylideneindolin-2-ones 2 in the presence of (R)-DPPOTMS/AcOH (R)-3/4b as a catalyst at room temperature. Chiral spiro[chroman-3,3′-indolin]-2′-ones 5 were transformed into the functionalized spiranes 7, 9, and 10 in good yields with high selectivity through Wittig, TCRA, acetal protection and reduction reactions, respectively. Supporting evidence for the reaction pathway through the formation of the important catalytic species of “aminals” was observed through NMR and ESI-HRMS analysis of an ongoing reaction between 1 and (R)-3 in CDCl3 and also shown by the structural requirement in hydroxyenals 1 to generate the “aminals” with (R)-3 through controlled experiments.

  成功实现了药物类似物功能化的Spiro[chroman-3,3′-indolin]-2′-酮5的非对称合成，该化合物含有三个相邻的立体中心，并具有高的二面体和对映选择性。通过在室温下，使用未修饰的羟基醛1与各种(E)-3-烯基吲哚-2-酮2的反射迈克尔（r-M）反应，在催化剂(R)-DPPOTMS/醋酸(R)-3/4b的存在下进行的合成。手性Spiro[chroman-3,3′-indolin]-2′-酮5经过维蒂希反应、TCRA反应、保护反应和还原反应相继转化为功能化的旋转体7、9和10，且均具有良好的产率和高选择性。通过NMR和ESI-HRMS分析观察到在CDCl3中1与(R)-3的进行反应中形成重要催化物种“亚胺”的反应途径的支持证据，并且通过对羟基醛1进行控制实验显示了生成“亚胺”与(R)-3之间的结构需求。
• Asymmetric Organocatalytic Michael Addition-Cyclization Cascade Reaction of Nitroalkanes with o-Hydroxycinnamaldehydes
  作者：Kwang-Su Choi、Sung-Gon Kim

  DOI：10.1002/ejoc.201101794

  日期：2012.2

  A catalytic enantioselective Michael addition–cyclization reaction of nitroalkanes with o-hydroxycinnamaldehydes has been established by using a diphenylprolinol TMS ether as an organocatalyst. The reaction afforded the corresponding 4-substituted chroman-2-ols in excellent yields with high levels of enantioselectivities (95 to >99 % ee).

  通过使用二苯基脯氨醇 TMS 醚作为有机催化剂，建立了硝基烷烃与邻羟基肉桂醛的催化对映选择性迈克尔加成环化反应。该反应以优异的收率和高水平的对映选择性（95 至 >99% ee）得到相应的 4-取代色满-2-醇。
• Regioselective Control of 1,2- Versus 1,4-Addition in Organocatalytic Reactions of o-Hydroxycinnamaldehydes with Organoboronic Acids
  作者：Sung-Gon Kim、Kwang-Su Choi

  DOI：10.1055/s-0030-1258268

  日期：2010.12

  The regioselective 1,2-addition and 1,4-addition reactions of o-hydroxycinnamaldehydes with organoboronic acids in the presence of organocatalysts gave 2-substituted 2H-chromenes and 4-substituted chroman-2-ols, respectively. Diethylamine was used as the catalyst for the 1,4-addition reaction, whereas dibenzyl­amine and trichloroacetic acid were used as the catalyst and additive, respectively, in the

  在有机催化剂存在下，邻羟基肉桂醛与有机硼酸的区域选择性1，2-加成和1，4-加成反应分别得到2-取代的2 H-色烯和4-取代的苯并吡喃-2-醇。二乙胺用作1，4-加成反应的催化剂，而二苄胺和三氯乙酸分别用作1，2-加成反应的催化剂和添加剂。 催化-加成反应-杂环-区域选择性-铬醇-色烯
• Organocatalytic Cascade Reactions: Towards the Diversification of Hydroisochromenes and Chromenes through Two Different Activation Modes
  作者：David Cruz Cruz、Rasmus Mose、Clarisa Villegas Gómez、Stine V. Torbensen、Martin S. Larsen、Karl Anker Jørgensen

  DOI：10.1002/chem.201403505

  日期：2014.9.1

  The organocatalytic enantioselective syntheses of functionalized hydroisochromenes and chromenes by trienamine‐mediated [4+2]‐cycloaddition/nucleophilic ring‐closing and iminium‐ion/aminal‐mediated oxa‐Michael/Michael/nucleophilic ring‐closing with 2‐nitroallylic alcohols are presented. The corresponding cycloadducts, with up to five stereocenters, are formed in good yield and excellent enantioselectivities

  介绍了由三烯胺介导的[4 + 2]-环加成/亲核开环和亚胺离子/氨基介导的氧杂-Michael / Michael /亲核与2-硝基烯丙醇成环的功能化氢异色酮和色烯的有机催化对映选择性合成。 。形成具有最多五个立体中心的相应的环加合物，具有良好的产率和优异的对映选择性。已经证明了所得产物的合成应用。