3-(3,4,5-三甲氧基苯基)-2-丙烯-1-醇 | 1504-56-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 中文名称: 3-(3,4,5-三甲氧基苯基)-2-丙烯-1-醇
• 英文名称: 3’,4’,5’-trimethoxycinnamyl alcohol
• 英文别名: 3',4',5'-trimethoxycinnamyl alcohol；3,4,5-trimethoxycinnamyl alcohol；3,4,5-dimethoxycinnamyl alcohol；4-O-methoxysinapyl alcohol；3-<3,4,5-Trimethoxy-phenyl>-prop-2-en-1-ol；3-(3,4,5-Trimethoxy-phenyl)-prop-2-en-1-ol；3-(3,4,5-Trimethoxyphenyl)-2-propen-1-ol；3-(3,4,5-trimethoxyphenyl)prop-2-en-1-ol
• CAS: 1504-56-9
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: HZDDMDAKGIRCPP-UHFFFAOYSA-N

物化性质

• 密度：
  1.12
• LogP：
  1.280 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2909499000

反应信息

• 作为反应物：
  描述：

  3-(3,4,5-三甲氧基苯基)-2-丙烯-1-醇 在 pyridinium chlorochromate absorbed on neutral alumina 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(2E)-3-(3,4,5-三甲氧基苯基)丙烯醛
  参考文献：
  名称：

  Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives

  摘要：

  Five series totalling 51 of sinapyl alcohol derivatives were designed and synthesized. Their cytotoxicity analyses were performed oil six human tumor cell lines Such as PC-3. CNE, KB, A549, BEL-7404, and HeLa. Certain sinapyl alcohol derivatives showed significant cytotoxic activities. Compound 14d exhibited especially potent cytotoxicity against the BEL-7404 cell line with an IC50 value of 0.7 mu M, which showed more cytotoxic activity than the positive control, cisplatin. The structure-cytotoxicity relationships were discussed and the CoMFA analysis was performed using the cytotoxic data against HeLa cells as a template. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.056
• 作为产物：
  描述：

  3,4,5-三甲氧基肉桂酸乙酯 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 3-(3,4,5-三甲氧基苯基)-2-丙烯-1-醇
  参考文献：
  名称：

  Synthesis of Some Phenylpropanoid Glycosides (PPGs) and Their Acetylcholinesterase/Xanthine Oxidase Inhibitory Activities

  摘要：

  在这项研究中，设计和合成了三类苯丙素糖苷（PPGs），以从红景天中分离的PPGs作为先导化合物。同时测试了它们对乙酰胆碱酯酶（AChE）和黄嘌呤氧化酶（XOD）的抑制能力。部分合成PPGs表现出了优异的酶抑制能力。

  DOI：

  10.3390/molecules16053580

文献信息

• Iridium-Catalyzed Dehydrogenative Decarbonylation of Primary Alcohols with the Liberation of Syngas
  作者：Esben P. K. Olsen、Robert Madsen

  DOI：10.1002/chem.201202631

  日期：2012.12.7

  A new iridium‐catalyzed reaction in which molecular hydrogen and carbon monoxide are cleaved from primary alcohols in the absence of any stoichiometric additives has been developed. The dehydrogenative decarbonylation was achieved with a catalyst generated in situ from [Ir(coe)2Cl]2 (coe=cyclooctene) and racemic 2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl (rac‐BINAP) in a mesitylene solution saturated

  一种新的铱-其中分子氢和一氧化碳从伯醇在不存在任何化学计量的添加剂的裂解催化反应已经研制成功。用[Ir（coe）2 Cl] 2（coe =环辛烯）和外消旋2,2'-双（二苯基膦基）-1,1'-联萘（rac）原位生成的催化剂完成脱氢脱羰作用。‐BINAP）在用水饱和的均三甲苯溶液中。还添加催化量的氯化锂以改善催化剂的周转率。该反应已应用于多种伯醇，并产生了产率高至优异的产物。醚，酯，酰亚胺和卤代芳基在反应条件下是稳定的，而烯烃是部分饱和的。据信，该反应是通过相同的铱（I）-BINAP物种催化的两个连续的有机金属转化而进行的。首先，将伯醇脱氢成相应的醛，然后将其脱羰基成具有少一个碳原子的产物。
• Catalytic Formal Conjugate Addition: Direct Synthesis of δ-Hydroxynitriles from Nitriles and Allylic Alcohols
  作者：Subramanian Thiyagarajan、Raman Vijaya Sankar、Puthannur K. Anjalikrishna、Cherumuttathu H. Suresh、Chidambaram Gunanathan

  DOI：10.1021/acscatal.1c05271

  日期：2022.2.18

  reactive functional groups such as carbamate, sulfonate, olefin, cyano, and trifluoromethyl-substituted benzyl nitriles. Homo allylic alcohols also provided 1,4-addition products following the isomerization of double bonds. Mechanistic studies supported that the allylic alcohols initially undergo selective oxidation by the catalyst to α,β-unsaturated carbonyl compounds followed by 1,4-conjugate addition

  醇和腈官能团在生化和化学合成中具有广泛的应用。依赖于不饱和偶联伙伴的涉及 C-C 键形成的催化转化为合成、材料和药物化学中的过程创造了重要的途径。描述了由钌钳形络合物催化的腈与烯丙醇的简单和选择性偶联的发现，其耐受反应性官能团，例如氨基甲酸酯、磺酸酯、烯烃、氰基和三氟甲基取代的苄腈。双键异构化后，高烯丙醇还提供 1,4-加成产物。机理研究支持烯丙醇最初通过催化剂选择性氧化为 α,β-不饱和羰基化合物，然后是 1，由碱催化的苄基腈的 4-共轭加成和随后的羰基官能团催化还原，导致形成 δ-羟基腈产物。这种串联过程的催化循环是通过密度泛函理论研究建立的。值得注意的是，使用这种催化方案成功合成了阿尼帕米药物。还证明了 δ-羟基腈产物在合成生物活性分子及其进一步功能化中的用途。
• Stereoselective allylation of isatinimines with γ-substituted allylboronic acids
  作者：Qiuyuan Tan、Xinqiao Wang、Lin Fu、Ling He、Min Zhang

  DOI：10.1016/j.tetlet.2021.153005

  日期：2021.4

  A highly efficient asymmetric allylboration of isatinimines with γ-substituted allylboronic acids under metal-free conditions was disclosed. Employing chiral amino alcohol as the chirality controller, the reaction proceeded with high efficiency and excellent stereoselectivity, providing a broad range of chiral 3-allyl-3-hydroxyethylamino oxindoles containing adjacent quaternary–tertiary stereocenters

  在无金属条件下，揭示了γ取代烯丙基硼酸的伊沙汀胺的高效不对称烯丙基硼化。采用手性氨基醇作为手性控制器，反应以高效率和出色的立体选择性进行，以高产率和优异的非对映选择性（高达 92% 的产率，>20：1 d.r.）提供广泛的手性 3-烯丙基-3-羟乙基氨基氧吲哚，其中包含相邻的季-叔级立体中心
• α-Quaternary Chiral Aldehydes from Styrenes, Allylic Alcohols, and Syngas via Multi-catalyst Relay Catalysis
  作者：Jing Meng、Lian-Feng Fan、Zhi-Yong Han、Liu-Zhu Gong

  DOI：10.1016/j.chempr.2018.03.010

  日期：2018.5

  synthesizes organic molecules, multi-catalyst relay catalysis (MCRC), based on the seamless combination of a series of catalytic reactions, has emerged as a promising strategy for achieving ideal synthesis. In such systems, each step takes place orderly and sequentially. Taken as a whole, the entire process appears indistinguishable from a common one-step reaction but provides a means for extraordinary transformations

  模仿自然界合成有机分子的方式，基于一系列催化反应的无缝结合的多催化剂中继催化（MCRC）已经成为实现理想合成的一种有前途的策略。在这样的系统中，每个步骤都按顺序和顺序进行。从整体上看，整个过程似乎与普通的一步反应没有区别，但为非凡的转化提供了一种手段。在此，我们报告了在由铑（I）络合物，钯（0）络合物，手性布朗斯台德酸催化剂组成的多催化剂体系中，将苯乙烯，烯丙基醇和合成气一步转化为α-季手性醛和非手性胺（20-100摩尔％）。
• Palladium-catalyzed synthesis of quinolines from allyl alcohols and anilines
  作者：Jingxiu Xu、Jing Sun、Jinwu Zhao、Bin Huang、Xiaohan Li、Yulun Sun

  DOI：10.1039/c7ra06425j

  日期：——

  A process for quinoline synthesis through palladium-catalyzed oxidative cyclization of aryl allyl alcohols and anilines is described. This process works in the absence of acid, base and any other additive and has a broad substrate scope, tolerating electron-withdrawing groups such as nitryl, trifluoromethyl and so on. A series of quinolines are prepared in satisfactory yields.

  描述了通过钯催化的芳基烯丙醇和苯胺的氧化环化合成喹啉的方法。该方法在不存在酸，碱和任何其他添加剂的情况下起作用，并且具有宽泛的底物范围，可以耐受吸电子基团，例如硝酰基，三氟甲基等。以令人满意的产率制备了一系列喹啉。