(E)-3-(4-hydroxy-3-methoxyphenyl)allyl acetate | 94930-81-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-3-(4-hydroxy-3-methoxyphenyl)allyl acetate
• 英文别名: coniferyl acetate；coniferyl-9-O-acetate；[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl] acetate
• CAS: 94930-81-1
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: XLZFUNZRKIQHOL-ONEGZZNKSA-N

物化性质

• LogP：
  2.392 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-hydroxy-3-methoxyphenyl)allyl acetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以100%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：

  Synthesis and reactivity of vinyl quinone methides

  摘要：

  DOI：

  10.1021/jo00207a006
• 作为产物：
  描述：

  丁香酚 在 溶剂黄146 、 silver(l) oxide 作用下， 以 四氯化碳 为溶剂， 反应 20.0h， 生成 (E)-3-(4-hydroxy-3-methoxyphenyl)allyl acetate
  参考文献：
  名称：

  Synthesis and reactivity of vinyl quinone methides

  摘要：

  DOI：

  10.1021/jo00207a006

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。
• Glycosides of 2,6-bis(hydroxy-phenyl)-3,7-dioxabicyclo [3,3,0] octane
  申请人：Wisconsin Alumni Research Foundation

  公开号：US04103006A1

  公开（公告）日：1978-07-25

  Mono- and di-glycosides of 2,6-bis (hydroxy-phenyl)-3,7-dioxabicyclo [3,3,0] octane and methods for preparing such compounds. The compounds exhibit anti-hypertensive properties.

  2,6-双（羟基苯基）-3,7-二氧杂双环[3,3,0]辛烷的单糖和双糖以及制备这些化合物的方法。这些化合物具有降压作用。
• Biosynthesis of <i>t</i>-Anethole in Anise: Characterization of <i>t</i>-Anol/Isoeugenol Synthase and an <i>O</i>-Methyltransferase Specific for a C7-C8 Propenyl Side Chain    
  作者：Takao Koeduka、Thomas J. Baiga、Joseph P. Noel、Eran Pichersky

  DOI：10.1104/pp.108.128066

  日期：2009.1.6

  The phenylpropene t-anethole imparts the characteristic sweet aroma of anise (Pimpinella anisum, family Apiaceae) seeds and leaves. Here we report that the aerial parts of the anise plant accumulate t-anethole as the plant matures, with the highest levels of t-anethole found in fruits. Although the anise plant is covered with trichomes, t-anethole accumulates inside the leaves and not in the trichomes or the epidermal cell layer. We have obtained anise cDNA encoding t-anol/isoeugenol synthase 1 (AIS1), an NADPH-dependent enzyme that can biosynthesize t-anol and isoeugenol (the latter not found in anise) from coumaryl acetate and coniferyl acetate, respectively. In addition, we have obtained a cDNA encoding S-[methyl-14C]adenosyl-l-methionine:t-anol/isoeugenol O-methyltransferase 1 (AIMT1), an enzyme that can convert t-anol or isoeugenol to t-anethole or methylisoeugenol, respectively, via methylation of the para-OH group. The genes encoding AIS1 and AIMT1 were expressed throughout the plant and their transcript levels were highest in developing fruits. The AIS1 protein is 59% identical to petunia (Petunia hybrida) isoeugenol synthase 1 and displays apparent K  m values of 145 μ  m for coumaryl acetate and 230 μ  m for coniferyl acetate. AIMT1 prefers isoeugenol to t-anol by a factor of 2, with K  m values of 19.3 μ  m for isoeugenol and 54.5 μ  m for S-[methyl-14C]adenosyl-l-methionine. The AIMT1 protein sequence is approximately 40% identical to basil (Ocimum basilicum) and Clarkia breweri phenylpropene O-methyltransferases, but unlike these enzymes, which do not show large discrimination between substrates with isomeric propenyl side chains, AIMT1 shows a 10-fold preference for t-anol over chavicol and for isoeugenol over eugenol.

  摘要：苯丙烯基丙烯醚对茴香（小茴香，伞形科）种子和叶子具有特有的甜香气味。本文报告了小茴香植物的地上部分随着植物成熟而积累苯丙烯基丙烯醚，其中果实中含有最高水平的苯丙烯基丙烯醚。尽管小茴香植物覆盖着毛茸茸的细胞，但苯丙烯基丙烯醚积累在叶子内部而不是细胞表皮或细胞外毛茸茸的层内。我们获得了编码t-anol/isoeugenol合酶1（AIS1）的小茴香cDNA，这是一种依赖于NADPH的酶，可以从香豆酸乙酯和香柏酸乙酯中生物合成t-anol和异丁香酚（后者在小茴香中不存在）。此外，我们还获得了编码S-[甲基-14C]腺苷-l-甲硫氨酸：t-anol/isoeugenol O-甲基转移酶1（AIMT1）的cDNA，这是一种酶，可以通过对对位-OH基团的甲基化将t-anol或异丁香酚转化为t-anethole或甲基异丁香酚。编码AIS1和AIMT1的基因在整个植物中表达，它们的转录水平在发育的果实中最高。AIS1蛋白与矮牵牛（Petunia hybrida）异丁香合酶1的相似性为59％，对香豆酸乙酯和香柏酸乙酯的显性Km值分别为145μm和230μm。AIMT1更喜欢异丁香酚而不是t-anol，其对S-[甲基-14C]腺苷-l-甲硫氨酸的Km值为19.3μm，对异丁香酚的Km值为54.5μm。AIMT1蛋白序列与罗勒（Ocimum basilicum）和Clarkia breweri苯丙烯基丙烯醚O-甲基转移酶大约相似40％，但与这些酶不同的是，它们在具有异构丙烯基侧链的底物之间不显示大的区分，而AIMT1则对t-anol比chavicol更倾向于异丁香酚比丁香酚更倾向于10倍。
• A pinoresinol–lariciresinol reductase homologue from the creosote bush (Larrea tridentata) catalyzes the efficient in vitro conversion of p-coumaryl/coniferyl alcohol esters into the allylphenols chavicol/eugenol, but not the propenylphenols p-anol/isoeugenol
  作者：Daniel G. Vassão、Sung-Jin Kim、Jessica K. Milhollan、Dietmar Eichinger、Laurence B. Davin、Norman G. Lewis

  DOI：10.1016/j.abb.2007.06.002

  日期：2007.9

  accumulates a complex mixture of 8-8' regiospecifically linked lignans, of which the potent antioxidant nordihydroguaiaretic acid (NDGA) is the most abundant. Its tetra-O-methyl derivative (M4N) is showing considerable promise in the treatment of refractory (hard-to-treat) brain and central nervous system tumors. NDGA and related 9,9'-deoxygenated lignans are thought to be formed by dimerization of allyl/propenyl

  杂酚丛（Larrea tridentata）积聚了8-8'区域特异性连接的木脂素的复杂混合物，其中有效的抗氧化剂去氢二氢愈创木酸（NDGA）最丰富。它的四-O-甲基衍生物（M4N）在治疗难治性（难治性）脑和中枢神经系统肿瘤方面显示出可观的前景。NDGA和相关的9,9'-脱氧木脂素被认为是由烯丙基/丙烯基酚（缺少C-9氧合的苯基丙烷化合物）的二聚作用形成的，从而将它们与更常见的单木酚衍生的木脂素区分开来。在我们正在进行的旨在阐明向NDGA及其同源物的生化途径的研究中，从三齿乳杆菌中分离了松脂醇-lariciresinol还原酶同源物，并以功能重组的形式获得了该蛋白。该蛋白质可有效催化对香豆油基和松柏油基醇酯转化为相应的烯丙基酚，香豆酚和丁香酚。在该酶反应过程中，它们均没有形成丙烯基苯酚区域异构体，对醇和异丁香酚。