ethyl 3-methoxy-3-phenylpropanoate | 60669-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3-methoxy-3-phenylpropanoate
• 英文别名: 3-methoxy-3-phenyl-propionic acid ethyl ester；3-Methoxy-3-phenyl-propionsaeure-aethylester；3-Phenyl-3-methoxy-propionsaeureaethylester
• CAS: 60669-59-2
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: NTSGGLIJZWCKRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  78-80 °C(Press: 0.1 Torr)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苄基氯甲基醚 在 乙醇 作用下， 生成 ethyl 3-methoxy-3-phenylpropanoate
  参考文献：
  名称：

  The Reaction of Ketene with Organic Halogen Compounds¹

  摘要：

  DOI：

  10.1021/ja01202a031

文献信息

• Synthesis of 3-Alkoxyalkanoic Esters from Acetals. A Novel Application of Reformatsky Reagents in Asymmetric Synthesis
  作者：Tiziana Basile、Emilio Tagliavini、Claudio Trombini、Achille Umani-Ronchi

  DOI：10.1055/s-1990-26859

  日期：——

  3-Alkoxyalkanoic esters are directly obtained in high yield from the reaction of acetals with Reformatsky reagents in the presence of titanium(IV) chloride or diethyl ether-boron trifluoride complex in dichloromethane. The reaction of ethyl 4-bromo-2-butenoate is regioselective, affording the product formed by attack on the 4-position. With chiral acetals as substrates, up to 84% enantiomerically enriched 3-hydroxyalkanoic esters can be prepared.

  3-烷氧基烷酸酯通过在四氯化钛或二氯甲烷中的二乙醚-三氟化硼复合物存在下，乙缩醛与Reformatsky试剂反应直接高产率地获得。乙基4-溴-2-丁烯酸酯的反应具有区域选择性，产物是由对4-位点的进攻形成的。以手性乙缩醛为底物时，可以制备出最高达84%的具有对映体富集的3-羟基烷酸酯。
• One-Pot Enol Silane Formation-Mukaiyama Aldol-Type Addition to Dimethyl Acetals Mediated by TMSOTf
  作者：C. Wade Downey、Miles W. Johnson、Kathryn J. Tracy

  DOI：10.1021/jo8001084

  日期：2008.4.1

  Various ketones, esters, amides, and thioesters add in high yield to dimethyl acetals in the presence of silyl trifluoromethanesulfonates and an amine base. Acetals derived from aryl, unsaturated, and aliphatic aldehydes are all effective substrates. The reaction proceeds in a single reaction flask, with no purification of the intermediate enol silane necessary.

  在三氟甲磺酸甲硅烷基酯和胺碱的存在下，各种酮，酯，酰胺和硫代酯以高收率添加到二甲基乙缩醛中。衍生自芳基，不饱和和脂族醛的缩醛都是有效的底物。反应在单个反应烧瓶中进行，无需纯化中间体烯醇硅烷。
• Reactivity of α-Metal(group 4) Esters. Lewis Acid Mediated Reactions of α-Triphenyltin Esters with Aldehydes and Acetals
  作者：Syun-ichi Kiyooka、Masumi Nakata

  DOI：10.1246/cl.1988.721

  日期：1988.4.5

  Ethyl triphenylstannylacetate and ethyl α-triphenylstannylpropionate reacted with aldehydes and acetals to give β-hydroxy and β-alkoxy esters at room temperature in the presence of TiCl4, in moderate yields. Under these conditions ethyl triphenylgermylacetate and ethyl trimethylsilylacetate did not work.

  三苯基甲锡基乙酸乙酯和α-三苯基甲锡基丙酸乙酯与醛和缩醛在室温下在TiCl4 存在下以中等产率反应生成β-羟基和β-烷氧基酯。在这些条件下，三苯基锗烷基乙酸乙酯和三甲基甲硅烷基乙酸乙酯不起作用。
• Organotin Perfluorooctanesulfonates as Air-Stable Lewis Acid Catalysts: Synthesis, Characterization, and Catalysis
  作者：De Lie An、Zhihong Peng、Akihiro Orita、Akinobu Kurita、Sumiyo Man-e、Kei Ohkubo、Xingshu Li、Shunichi Fukuzumi、Junzo Otera

  DOI：10.1002/chem.200501091

  日期：2006.2.8

  organic solvents. The ionic dissociation together with facile hydration probably causes the unusual solubility. The Lewis acidity of these compounds was found to be high among organotin derivatives on the basis of ESR spectra of superoxide/metal-ion complexes. In contrast to well-known organotin triflates, these compounds suffered no hydrolysis upon storage in open air. The high catalytic activity of the

  1,3-二氯-1,1,3,3-四丁基二锡烷和二烷基锡二卤化物与全氟辛烷磺酸银的反应提供了相应的磺酸盐水合物。水合的水分子数（n）取决于条件。双锡氧烷衍生物的n值为0.5至6，而在水合单核物质和DMSO络合物中，n的范围为4至13。这些化合物在极性有机溶剂中显示出异常高的溶解度。离子离解和容易的水合作用可能会导致异常的溶解性。根据超氧化物/金属离子络合物的ESR光谱，发现这些化合物的路易斯酸度在有机锡衍生物中较高。与众所周知的有机锡三氟甲磺酸盐相反，这些化合物在露天储存后不会发生水解。对于各种碳-碳键形成反应，例如Mukaiyama-aldol以及-Michael反应和醛的烯丙基化，例举了二锡氧烷1的高催化活性。
• Condensation of Reformatsky reagents with acetals in the presence of TiCl₄: a novel entry to enantiomerically-enriched β-hydroxy-esters
  作者：Tiziana Basile、Emilio Tagliavini、Claudio Trombini、Achille Umani-Ronchi

  DOI：10.1039/c39890000596

  日期：——

  3-Alkoxy esters are prepared in high yield from the reaction of ethyl zinc-bromoacetate and acetals in the presence of TiCl4 under very mild conditions; using chiral acetals the corresponding 3-hydroxy esters have been obtained in fair enantiomeric excess.

  在非常温和的条件下，在TiCl 4的存在下，由溴乙酸锌锌乙酯和乙缩醛反应高产率地制备3-烷氧基酯。使用手性缩醛，已经以相当的对映体过量获得了相应的3-羟基酯。