(E)-3-methoxyprop-2-enyl acetate | 163271-96-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-3-methoxyprop-2-enyl acetate
• 英文别名: acetic acid 3-methoxy-allyl ester；[(E)-3-methoxyprop-2-enyl] acetate
• CAS: 163271-96-3
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: DKVKUDPLONKUMS-ONEGZZNKSA-N

物化性质

• 沸点：
  167.1±23.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  烯丙基丙二酸二乙酯 、 (E)-3-methoxyprop-2-enyl acetate 在 四(三苯基膦)钯 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到Diethyl 2-(1-methoxyprop-2-enyl)-2-prop-2-enylpropanedioate
  参考文献：
  名称：

  1-烷氧基π-烯丙基铝配合物的反应性

  摘要：

  钯催化的3-烷氧基-2-丙烯基乙酸酯和碳酸酯被各种亲碳亲核剂的烯丙基取代发生在烷氧基的α处。

  DOI：

  10.1016/0040-4039(94)02334-8
• 作为产物：
  描述：

  乙酸酐 、 3-methoxy-2-propen-1-ol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (E)-3-methoxyprop-2-enyl acetate
  参考文献：
  名称：

  Highly Enantio- and Regioselective Allylic Alkylations Catalyzed by Chiral [Bis(dihydrooxazole)]molybdenum Complexes

  摘要：

  A series of chiral C-2-symmetric bis[dihydrooxazoles] with a trans-1,2-diaminocyclohexane backbone was synthesized. In view of the promising results obtained by Trost et al with related bis[pyridine] ligands, we tested these new ligands in the enantioselective molybdenum-catalyzed allylic alkylation of 1- and 3-monosubstituted allylic substrates. Enantiomer excesses of up to 98% and branched/linear ratios of up to 11 : 1 were obtained with (E)-3-(alkyl)allyl carbonates. (E)-3-Phenoxyallyl acetate gave a branclied/linear ratio of > 20:1 and an ee of 98%. Crystal structures of the free ligand 7a and of its tricarbonylmolybdenum(0) complex 28 are reported.

  DOI：

  10.1002/1522-2675(20011017)84:10<3178::aid-hlca3178>3.0.co;2-q

文献信息

• Chiral Phosphoric Acid-Catalyzed Enantio- and Diastereoselective Allylboration of Aldehydes with β,γ-Substituted Allylboronates
  作者：Jinping Yuan、Pankaj Jain、Jon C. Antilla

  DOI：10.1021/acs.joc.2c00764

  日期：2022.6.17

  The catalytic asymmetric addition of β,γ-substituted allylboronates to aldehydes has been described. Promoted by 5 mol % chiral phosphoric acid, the reactions were broadly applicable, scalable, and efficient, allowing for the formation of 3,4-anti/syn-homoallylic alcohols bearing adjacent tertiary or quaternary stereogenic centers in a highly enantio- and diastereoselective manner (≤99% ee and dr >20:1)

  已经描述了 β,γ-取代的烯丙基硼酸酯对醛的催化不对称加成。在 5 mol% 手性磷酸的促进下，该反应具有广泛的适用性、可扩展性和高效性，允许以高度对映和非对映选择性的方式形成带有相邻叔或季立体中心的 3,4-反/同-高烯丙醇（≤99% ee 和 dr >20:1）。涉及手性磷酸的刚性椅子状过渡态有助于高度控制的反应。
• Enantioselective Molybdenum-Catalyzed Allylic Alkylation Using Chiral Bisoxazoline Ligands
  作者：Frank Glorius、Andreas Pfaltz

  DOI：10.1021/ol990602r

  日期：1999.7.1

  [GRAPHICS]A series of chiral C-2-symmetric bisoxazolines with trans-1,2-diaminocyclohexane backbones was synthesized. In View of the promising results obtained by Trost with analogous bispyridine ligands, we tested our new ligands in the enantioselective molybdenum-catalyzed allylic alkylation of 1- and 3-monosubstituted allylic substrates, Enantiomeric excesses of up to 98% and branched/linear ratios of up to 11:1 were obtained with (E)-3-(n-alkyl)allyl carbonates. (E)-3-Phenoxyallyl acetate gave a branched/linear ratio of >20:1 and an ee of 98%.
• Reactivity of 1-alkoxy π-allylpalladium complexes
  作者：Nicolas Vicart、Bernard Cazes、Jacques Goré

  DOI：10.1016/0040-4039(94)02334-8

  日期：1995.1

  The palladium-catalyzed allylic substitution of 3-alkoxy-2-propenyl acetates and carbonates with various carbonucleophiles occurs alpha to the alkoxy group.

  钯催化的3-烷氧基-2-丙烯基乙酸酯和碳酸酯被各种亲碳亲核剂的烯丙基取代发生在烷氧基的α处。
• Highly Enantio- and Regioselective Allylic Alkylations Catalyzed by Chiral [Bis(dihydrooxazole)]molybdenum Complexes
  作者：Frank Glorius、Markus Neuburger、Andreas Pfaltz

  DOI：10.1002/1522-2675(20011017)84:10<3178::aid-hlca3178>3.0.co;2-q

  日期：2001.10.17

  A series of chiral C-2-symmetric bis[dihydrooxazoles] with a trans-1,2-diaminocyclohexane backbone was synthesized. In view of the promising results obtained by Trost et al with related bis[pyridine] ligands, we tested these new ligands in the enantioselective molybdenum-catalyzed allylic alkylation of 1- and 3-monosubstituted allylic substrates. Enantiomer excesses of up to 98% and branched/linear ratios of up to 11 : 1 were obtained with (E)-3-(alkyl)allyl carbonates. (E)-3-Phenoxyallyl acetate gave a branclied/linear ratio of > 20:1 and an ee of 98%. Crystal structures of the free ligand 7a and of its tricarbonylmolybdenum(0) complex 28 are reported.