2-甲氧基丙醛 | 6142-38-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-甲氧基丙醛
• 英文名称: 2-methoxypropanal
• 英文别名: 2-methoxy-propionaldehyde；2-Methoxy-propionaldehyd；2-methoxy-propanal
• CAS: 6142-38-7
• 化学式: C₄H₈O₂
• 分子量: 88.1063
• InChiKey: HZVKHMQXJYFYRF-UHFFFAOYSA-N

物化性质

• LogP：
  -0.300 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲氧基丙醛 、 tert-butyl 2-(triphenylphosphoranylidene)propionate 以 苯 为溶剂， 生成 (E)-4-Methoxy-2-methyl-pent-2-enoic acid tert-butyl ester
  参考文献：
  名称：

  Highly Diastereoselective Conjugate Addition of Lithium Dialkylamides to α,β-Unsaturated Esters Having a Chiral Center at the γ-Position

  摘要：

  The conjugate addition of lithium amides 2 to tert-butyl 4-(OR)-substituted-2-pentenoates 1 produced a mixture of the syn-and anti-amino esters (3 and 4) in high yields. Sterically bulky OR groups, such as trityloxy and tert-butyldiphenylsilyloxy, gave the syn diastereomer 3 either exclusively or predominantly. The syn-selectivity may be explained by a modified Felkin-Anh model. The use of tert-butyldimethylsilyloxy as an OR group afforded a nearly 1:1 mixture of diastereoisomers, and the use of the smallest MeO group produced a 63:37 mixture of the syn 3 and anti isomer 4. The presence of Me group at the alpha-position (C-2 position) of the enoate enhanced the syn diastereoselectivity up to 100%; the conjugate addition to tert-butyl 4-methoxy-2-methyl-2-pentenoate (17) gave the syn-isomer 18 exclusively. This enhancement may be explained by the combination of chelation and allylic strain model 19 in which the smallest H orients inside to avoid an allylic strain. A phenyl group at the gamma-position enhanced the anti selectivity in the case of gamma-alkoxy-alpha,beta-enoates such as isopropyl 4-[(tert-butyldimethylsilyl)oxy]-4-phenyl-2-buteonoate (20), and in the case of gamma-alkyl-alpha,beta-enoates such as tert-butyl 4-phenyl-2-pentenoate (27).

  DOI：

  10.1021/jo970435d
• 作为产物：
  描述：

  O-甲基-L-乳酸乙酯 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 1.58h， 生成 2-甲氧基丙醛
  参考文献：
  名称：

  Highly Diastereoselective Conjugate Addition of Lithium Dialkylamides to α,β-Unsaturated Esters Having a Chiral Center at the γ-Position

  摘要：

  The conjugate addition of lithium amides 2 to tert-butyl 4-(OR)-substituted-2-pentenoates 1 produced a mixture of the syn-and anti-amino esters (3 and 4) in high yields. Sterically bulky OR groups, such as trityloxy and tert-butyldiphenylsilyloxy, gave the syn diastereomer 3 either exclusively or predominantly. The syn-selectivity may be explained by a modified Felkin-Anh model. The use of tert-butyldimethylsilyloxy as an OR group afforded a nearly 1:1 mixture of diastereoisomers, and the use of the smallest MeO group produced a 63:37 mixture of the syn 3 and anti isomer 4. The presence of Me group at the alpha-position (C-2 position) of the enoate enhanced the syn diastereoselectivity up to 100%; the conjugate addition to tert-butyl 4-methoxy-2-methyl-2-pentenoate (17) gave the syn-isomer 18 exclusively. This enhancement may be explained by the combination of chelation and allylic strain model 19 in which the smallest H orients inside to avoid an allylic strain. A phenyl group at the gamma-position enhanced the anti selectivity in the case of gamma-alkoxy-alpha,beta-enoates such as isopropyl 4-[(tert-butyldimethylsilyl)oxy]-4-phenyl-2-buteonoate (20), and in the case of gamma-alkyl-alpha,beta-enoates such as tert-butyl 4-phenyl-2-pentenoate (27).

  DOI：

  10.1021/jo970435d

文献信息

• Acyclic stereoselection. 40. Steric effects, as well as .sigma.*-orbital energies, are important in diastereoface differentiation in additions to chiral aldehydes
  作者：Eric P. Lodge、Clayton H. Heathcock

  DOI：10.1021/ja00245a027

  日期：1987.5

  Etude des reactions d'aldolisation de deux series d'aldehydes chiraux avec l'enolate de lithium de la pinacolone

  练习曲 d'aldolisation de deux series d'aldehydes chiraux avec l'enolate delithium de la pinacolone
• Preparation of 2-methoxy-1-alkanols and 2-methoxy-1-alkanals
  申请人：DU PONT

  公开号：US02555950A1

  公开（公告）日：1951-06-05
• Boche, Gernot; Bosold, Ferdinand; Lohrenz, John C. W., Chemische Berichte, 1993, vol. 126, # 8, p. 1873 - 1886
  作者：Boche, Gernot、Bosold, Ferdinand、Lohrenz, John C. W.、Opel, Achim、Zulauf, Peter

  DOI：——

  日期：——
• Factors affecting the regioselectivity in the rhodium-catalysed hydroformylation of vinyl ethers
  作者：Raffaello Lazzaroni、Sergio Bertozzi、Paolo Pocai、Francesco Troiani、Piero Salvadori

  DOI：10.1016/0022-328x(85)80321-1

  日期：1985.11
• LODGE E. P.; HEATHCOCK C. H., J. AMER. CHEM. SOC., 109,(1987) N 11, 3353-3361
  作者：LODGE E. P.、 HEATHCOCK C. H.

  DOI：——

  日期：——