3-(4'-methoxyphenyl)propyl-3-(4'-methoxyphenyl)propanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4'-methoxyphenyl)propyl-3-(4'-methoxyphenyl)propanoate
• 英文别名: 3-(4-methoxyphenyl)propyl 3-(4-methoxyphenyl)propanoate
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: USGSPXNFFGCQDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  反式-4-甲氧基肉桂酸 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 3-(4'-methoxyphenyl)propyl-3-(4'-methoxyphenyl)propanoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues

  摘要：

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.

  DOI：

  10.1021/np0496441

文献信息

• Facile oxidative conversion of alcohols to esters using molecular iodine
  作者：Naoshi Mori、Hideo Togo

  DOI：10.1016/j.tet.2005.03.097

  日期：2005.6

  A simple, efficient, and high-yield procedure for the oxidative conversion of alcohols to various types of esters and ketones, with molecular iodine and potassium carbonate was successfully carried out.

  成功地进行了一种简单，高效且高收率的方法，将醇与分子碘和碳酸钾氧化转化为各种类型的酯和酮。
• Enantioselective Synthesis of cis-1,2-Disubstituted Cyclopentanes and Cyclohexanes by Suzuki-Miyaura Cross-Coupling and Iridium-Catalyzed Asymmetric Hydrogenation
  作者：Andreas Schumacher、Marcus G. Schrems、Andreas Pfaltz

  DOI：10.1002/chem.201102650

  日期：2011.11.25

  using phosphinomethyloxazolines as ligands. Asymmetric hydrogenation of analogous cyclopentene derivatives, prepared by Suzuki–Miyaura cross‐coupling, proved to be more difficult and proceeded with lower enantioselectivities of up to 88 % ee. The synthetic potential of this cross‐coupling/asymmetric‐hydrogenation strategy was demonstrated by an enantioselective route to chiral hexahydrofluorenones.

  通过Suzuki-Miyaura将2-溴-1-环己烯甲醛或2-羰甲氧基-1-环己烯-1-基三氟甲磺酸酯与芳基硼酸酯的交叉偶联制备了一系列1,2-二取代的环己烯衍生物。这些四取代的环状烯烃经过Ir催化的不对称氢化反应。通过使用膦基甲基恶唑啉作为配体，以这种方式以高收率获得了具有高对映选择性和非对映选择性（高达> 99％ee，> 99％ 顺式）的顺-1-甲氧基甲基-2-芳基环己烷 。Suzuki-Miyaura交叉偶合制备的类似环戊烯衍生物的不对称氢化被证明更困难，并且对映体选择性较低，最高可达88％  ee。这种交叉偶联/不对称氢化策略的合成潜力通过手性六氢芴酮的对映选择性途径得到证明。
• Solvent-free selective oxidation of primary alcohols-to-aldehydes and aldehydes-to-carboxylic acids by molecular oxygen over MgO-supported nano-gold catalyst
  作者：Vasant R. Choudhary、Deepa K. Dumbre

  DOI：10.1016/j.catcom.2011.07.001

  日期：2011.10

  Magnesium oxide supported nano-gold catalyst (prepared by the homogeneous deposition precipitation technique) showed high activity/selectivity and excellent reusability in the oxidation of different primary alcohols and aldehydes to corresponding aldehydes and carboxylic acids, respectively, by molecular oxygen (under atmospheric pressure) in the absence of any solvent. Influence of the catalyst calcination temperature (400-900 degrees C), reaction temperature (50-120 degrees C) and use of different solvents (viz. toluene. p-xylene, DMF or DMSO) on the oxidation reaction has also been studied. (C) 2011 Published by Elsevier B.V.
• Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues
  作者：Li Hong Hu、Hong Bin Zou、Jing Xu Gong、Hai Bo Li、Lei Xiang Yang、Wei Cheng、Chang Xin Zhou、Hua Bai、Françoise Guéritte、Yu Zhao

  DOI：10.1021/np0496441

  日期：2005.3.1

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.