(R)-(+)-4-(4'-hydroxyphenyl)-2-butyl acetate | 129752-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (R)-(+)-4-(4'-hydroxyphenyl)-2-butyl acetate
• 英文别名: (R)-2-acetoxy-4-(4-hydroxyphenyl)butane；[(2R)-4-(4-hydroxyphenyl)butan-2-yl] acetate
• CAS: 129752-69-8
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: SIAARBXVWRWGGR-SECBINFHSA-N

物化性质

• 沸点：
  332.4±25.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (R)-(+)-4-(4'-hydroxyphenyl)-2-butyl acetate 在 咪唑 、 4-二甲氨基吡啶 、 碘苯二乙酸 、 四丁基氟化铵 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 (R)-4-(3-hydroxybutyl)-4-hydroxy-2,5-cyclohexadien-1-one
  参考文献：
  名称：

  Cephalosporolide B Serving as a Versatile Synthetic Precursor: Asymmetric Biomimetic Total Syntheses of Cephalosporolides C, E, F, G, and (4-OMe-)G

  摘要：

  Cephalosporolide B (Ces-B) was efficiently synthesized and exploited for the first time as a versatile biomimetic synthetic precursor for the chemical syntheses of not only cephalosporolides C, G, and (4-OMe-) G via a challenging diastereoselective oxa-Michael addition but also the structurally unprecedented cephalosporolides E and F via a novel biomimetic ring-contraction rearrangement. These findings provide the first direct chemical evidence that Ces-B may be the true biosynthetic precursor of cephalosporolides.

  DOI：

  10.1021/ol402913m
• 作为产物：
  描述：

  4-(对羟基苯基)-2-丁醇 在 吡啶 、 Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W₁₁₀A mutant 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 异丙醇 、 丙酮 为溶剂， 反应 54.0h， 生成 (R)-(+)-4-(4'-hydroxyphenyl)-2-butyl acetate
  参考文献：
  名称：

  使用单个酒精脱氢酶对仲醇进行脱硝

  摘要：

  我们开发了一种单酶介导的两步法来对仲醇进行脱脂。乙醇嗜热厌氧菌仲醇脱氢酶的单个突变体能够使外消旋醇非立体选择性氧化为酮，然后进行立体选择性还原过程。改变丙酮和2-丙醇共底物的量分别控制连续氧化和还原反应的立体选择性。我们使用一种酶完成了仲醇的脱硝作用，一锅中的ee高达99％以上，回收率达到99.5％以上，而无需分离前手性酮中间体。

  DOI：

  10.1002/cctc.201600160

文献信息

• Scalable Green Approach Toward Fragrant Acetates
  作者：Eva Puchl’ová、Peter Szolcsányi

  DOI：10.3390/molecules25143217

  日期：——

  acetylation of (hydroxyalkyl) phenols as well as for the kinetic resolution of chiral secondary alcohols. Lastly, its discrimination power was demonstrated in competitive experiments of equimolar mixtures of two isomeric alcohols. This enabled the practical synthesis of 1-pentyl acetate isolated as a single product in 68% yield from the equimolar mixture of 1-pentanol and 3-pentanol.

  乙二醇二乙酸酯 (EGDA) 的优越特性使其成为三乙酸甘油酯 (GTA) 的有用替代品，可用于各种绿色应用。我们在纯 EGDA 中仔细检查了脂肪酶介导的结构不同醇的乙酰化，提供了一系列天然存在的芳香乙酸酯。我们发现这种酶促系统对活化的（同型）烯丙基和未活化的伯/仲醇表现出高反应性和选择性。该特征用于以 70% 的产率对芳香 (Z)-hex-3-en-1-yl 乙酸酯进行可扩展的多克合成。此外，还发现 Lipozyme 435/EGDA 系统适用于（羟烷基）酚的化学选择性乙酰化以及手性仲醇的动力学拆分。最后，两种异构醇的等摩尔混合物的竞争实验证明了它的辨别能力。这使得能够从 1-戊醇和 3-戊醇的等摩尔混合物中以 68% 的收率实际合成作为单一产物分离的 1-戊基乙酸酯。
• 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。
• Asymmetric synthesis of enantiomerically pure zingerols by lipase-catalyzed transesterification and efficient synthesis of their analogues
  作者：Takashi Kitayama、Sachiko Isomori、Kaoru Nakamura

  DOI：10.1016/j.tetasy.2013.04.013

  日期：2013.6

  readily available from ginger, can be easily transformed into chiral derivatives. Zingerol 2, a reduced product of zingerone 1 is expected to be an important new medicinal lead compound. We have achieved a concise synthesis of optically active zingerol (R)-2 and (S)-2 by the lipase-catalyzed stereoselective transesterification of racemic 2. Under the optimized conditions, a lipase from Alcaligenes sp

  容易从姜中获得的非手性姜油酮1可以容易地转化为手性衍生物。姜油酮1的还原产物Zingerol 2被认为是重要的新药用铅化合物。我们已经通过脂肪酶催化的消旋体2的立体选择性酯交换反应实现了光学活性姜油醇（R）-2和（S）-2的简明合成。在优化的条件下，来自Alcaligenes sp。的脂肪酶。（Meito QLM）和乙酸乙烯酯在i -Pr 2 O或己烷中于35°C在1小时内得到醇（S）-2和具有高对映选择性的乙酸盐（R）-9而不会产生乙酰化的副产物。由于通过脂肪酶催化的酯交换反应获得了旋光性（S）-2和（R）-9，因此可以合成其他对映体纯的新型化合物。
• Resolution of Racemic Rhododendrol by Lipase-Catalyzed Enantioselective Acetylation
  作者：Yoshifumi Yuasa、Shiroshi Shibuya、Yoko Yuasa

  DOI：10.1081/scc-120018756

  日期：2003.1.5

  Both (R)- and (S)-enantiomers of rhododendrot were prepared in high enantiomeric exess by lipase from Pseudomonas cepacia (Amano PS)-catalyzed acetylation of racemic 1 with vinyl acetate at room temperature. Especially, in the case of using acetonitrile as the solvent, by-products 4 and 5 were minimized.
• Asymmetric Transformations of Acyloxyphenyl Ketones by Enzyme−Metal Multicatalysis
  作者：Mahn-Joo Kim、Min Young Choi、Min Young Han、Yoon Kyung Choi、Jae Kwan Lee、Jaiwook Park

  DOI：10.1021/jo026122m

  日期：2002.12.1

  A multipathway process comprising several enzyme- and metal-catalyzed reactions has been explored for the asymmetric transformations of acyloxyphenyl ketones to optically active hydroxyphenyl alcohols in the ester forms. The process comprises nine component reactions in three pathways, all of which take place by the catalytic actions of only two catalysts, a lipase and a ruthenium complex. The synthetic reactions were carried out on 0.2-0.6 mmol scales for eight different substrates under an atmosphere of hydrogen (I atm) in toluene at 70 degreesC for 3 days. In most cases, the yields were high (92-96%) and the optical purities were excellent (96-98% ee), This work thus has demonstrated that enzyme-metal multicatalysis has great potential as a new methodology for asymmetric transformations.