(2E)-3-(4-O-acetyl-3-methoxyphenyl)prop-2-en-1-yl acetate | 37791-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (2E)-3-(4-O-acetyl-3-methoxyphenyl)prop-2-en-1-yl acetate
• 英文别名: (E)-3-(4-acetoxy-3-methoxyphenyl)allyl acetate；trans-coniferyl alcohol diacetate；4,9-diacetyl-coniferol；4,9-diacetylconiferol；1-acetoxy-4-(3-acetoxy-trans-propenyl)-2-methoxy-benzene；1-Acetoxy-4-(3-acetoxy-trans-propenyl)-2-methoxy-benzol；[(E)-3-(4-acetyloxy-3-methoxyphenyl)prop-2-enyl] acetate
• CAS: 37791-78-9
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: KCODNVFFXXYJPA-SNAWJCMRSA-N

物化性质

• 沸点：
  383.0±37.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E)-3-(4-O-acetyl-3-methoxyphenyl)prop-2-en-1-yl acetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇
  参考文献：
  名称：

  Lindeberg, Otto, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1980, vol. 34, # 1, p. 15 - 20

  摘要：

  DOI：
• 作为产物：
  描述：

  阿魏酸甲酯 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (2E)-3-(4-O-acetyl-3-methoxyphenyl)prop-2-en-1-yl acetate
  参考文献：
  名称：

  Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs

  摘要：

  A new coniferol derivative, named as tripolinolate A (1), and 11 known compounds (2-12) were isolated from whole plants of Tripolium vulgare Nees. The structure of this new compound was determined as 4-(2S-methylbutyryl)-9-acetyl-coniferol based on its NMR and HRESIMS spectral analyses. A simple and efficient method was designed to prepare tripolinolate A and its 19 analogs including nine new chemical entities for bioactive assay. Tripolinolate A and its analog 4,9-diacetyl-coniferol were found to be the two most active compounds that significantly inhibited the proliferation of different cancer cell lines with IC50 values ranging from 0.36 to 12.9 mu M and induced apoptosis in tumor cells. Structure-activity relationship analysis suggested that the molecular size of acyl moieties at C-4 and C-9 position might have an effect on the activity of this type of coniferol derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.091

文献信息

• Part 148 in the Series “Studies on Novel Synthetic Methodologies:” Selective Acetylation of Alcohols, Phenols and Amines and Selective Deprotection of Aromatic Acetates using Silica-Supported Phosphomolybdic Acid
  作者：Biswanath Das、Ponnaboina Thirupathi、Rathod Aravind Kumar、Keetha Laxminarayana

  DOI：10.1002/adsc.200700292

  日期：2007.12.10

  efficient catalyst for the selective acetylation of alcohols, phenols and amines in the absence of any solvent and also for the chemoselective deprotection of aromatic acetates under very mild conditions. This method has been used for the protection of the hydroxy groups as well as for the deprotection of the acetates of several naturally occurring bioactive phenolic compounds. The catalyst can be easily

  发现环保的二氧化硅负载的磷钼酸是在没有任何溶剂的情况下用于醇，酚和胺的选择性乙酰化以及在非常温和的条件下用于芳族乙酸酯的化学选择性脱保护的高效催化剂。该方法已用于保护羟基以及几种天然存在的生物活性酚类化合物的乙酸酯的脱保护。该催化剂可以容易地回收和再利用。
• Ruthenium-Catalyzed Cross-Metathesis of Allyl Acetate and Styrenes: A Practical Approach to the Synthesis of Tripolinolate A and Its Analogs
  作者：Yasuhiro Araki、Nikola Topolovčan、Martin Kotora

  DOI：10.1002/ejoc.201700132

  日期：2017.4.3

  structurally divergent styrenes were tolerated, and the resultant products were obtained in reasonable yields. The reported method was utilized in the synthesis of inhibitors of the proliferation of glioma and colorectal cancer cells, tripolinolate A and its diacetate analog.

  探索了 Ru 催化的乙酸烯丙酯和苯乙烯交叉复分解的范围。可以容忍各种电子和结构不同的苯乙烯，并以合理的产率获得所得产物。所报道的方法用于合成胶质瘤和结直肠癌细胞增殖抑制剂、三萜醇酯 A 及其二乙酸酯类似物。
• Spectral comparisons of coniferyl and cinnamyl alcohol epoxide derivatives with a purported cis-epoxyconiferyl alcohol isolate
  作者：Nathan R. Guz、Frank R. Stermitz

  DOI：10.1016/s0031-9422(00)00101-1

  日期：2000.8

  The reported isolation of cis-epoxyconiferyl alcohol must be incorrect, based upon comparison of the reported Nuclear Magnetic Resonance (NMR) spectral data for the isolate with those for synthesized coniferyl and cinnamyl alcohol epoxide derivatives. Attempts to prepare cis- and trans-coniferyl alcohols were unsuccessful, although their acetate derivatives could be synthesized. The NMR spectral data

  根据报告的分离物核磁共振 (NMR) 光谱数据与合成的松柏醇和肉桂醇环氧化物衍生物的数据进行比较，报告的顺式环氧松柏醇的分离肯定是不正确的。尝试制备顺式和反式松柏醇没有成功，尽管可以合成它们的乙酸酯衍生物。松脂醇合成样品的 NMR 光谱数据与声称的分离物的数据非常一致。
• Derivatives of unsaturated aromatic alcohols in propolis and styrax benzoin
  作者：S. A. Popravko、I. V. Sokolov、I. V. Torgov

  DOI：10.1007/bf00579470

  日期：——
• DFRC Method for Lignin Analysis. 1. New Method for β-Aryl Ether Cleavage:  Lignin Model Studies
  作者：Fachuang Lu、John Ralph

  DOI：10.1021/jf970539p

  日期：1997.12.1

  A new method for selective and efficient cleavage of arylglycerol-beta-aryl (beta-O-4) ether linkages in lignins is described and applied to several Lignin beta-ether models. The term "DFRC" was coined for derivatization followed by reductive cleavage. Derivatization, accompanied by cell wall solubilization, is accomplished with acetyl bromide (AcBr); reductive cleavage of resulting beta-bromo ethers utilizes zinc in acetic acid. Degradation monomers, 4-acetoxycinnamyl acetates, from beta-ether cleavage by the DFRC method were identified by NMR, CC-MS, and comparison of GC retention times with authentic compounds. Under the conditions used in this study, the beta-ether linkage of all models was cleaved in very high (> 92%) yield. The DFRC method produces simpler mixtures of monomers with higher yields than alternative hydrolytic methods. Because of its relative simplicity, mild conditions, and exceptional selectivity, this method should become a powerful analytical method for lignin characterization.