2-Methoxymethoxy-propionaldehyde | 145102-74-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methoxymethoxy-propionaldehyde
• 英文别名: 2-Methoxymethoxypropanal；2-(methoxymethoxy)propanal
• CAS: 145102-74-5
• 化学式: C₅H₁₀O₃
• 分子量: 118.133
• InChiKey: DCVYJILSQVNHOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  2-Methoxymethoxy-propionaldehyde 在 4 A molecular sieve 、 三氟化硼乙醚 、 甲基锂 、 lithium bromide 作用下， 以 甲苯 、 苯 为溶剂， 反应 1.0h， 生成 (S^*,S^*)-4,4,5,5,6,6,7,7,8,8,9,9,9-Tridecafluoro-2-(methoxymethoxy)-N-propyl-3-nonylamine
  参考文献：
  名称：

  Boron trifluoride-assisted perfluoroalkylation of carbon-nitrogen double bonds

  摘要：

  In the presence of BF3.OEt2, (perfluoroalkyl)lithiums generated in situ from the reaction of primary perfluoroalkyl iodides and MeLi-LiBr reacted with imines, azines, and nitrones to afford perfluoroalkylated nitrogen-containing compounds in moderate to good yields. This method was successfully applied to the preparation of a (perfluoroalkyl)glycine and optically active perfluoroalkylated amines.

  DOI：

  10.1021/jo00031a032
• 作为产物：
  描述：

  Ethyl 2-(methoxymethoxy)propanoate 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 生成 2-Methoxymethoxy-propionaldehyde
  参考文献：
  名称：

  Hydroxynitrile lyase catalyzed enantioselective HCN addition to O-protected α-hydroxyaldehydes

  摘要：

  Various O-protected glycol- and racemic lactaldehydes 3 and 6 as well as O-allyl protected racemic alpha-hydroxyaldehydes 7 (R-1=Et Pr, Bu) have been prepared to investigate and perform a stereoselective Kiliani-Fischer synthesis by hydroxynitrile lyase (HNL) catalyzed addition of HCN. From all protecting groups investigated the allyl moiety was most suitable. (R)-PaHNL from bitter almonds (Prunus amygdalus), yielding the (2S)-cyanohydrins 8-10, was found to be a more stereoselective catalyst than (S)-MeHNL from maniok (Manihot esculenta). While (R)-PaHNL led to enantiomeric excesses greater than or equal to 93%, with (S)-MeHNL the (2R)-cyanohydrins 8-10 were obtained with enantiomeric excesses less than or equal to 78%. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00275-x

文献信息

• C−C-Bond Formation by the Palladium-Catalyzed Cycloisomerization/Dimerization of Terminal Allenyl Ketones:  Selectivity and Mechanistic Aspects
  作者：A. Stephen K. Hashmi、Thorsten L. Ruppert、Thomas Knöfel、Jan W. Bats

  DOI：10.1021/jo970837l

  日期：1997.10.1

  conditions, besides the normal functional group tolerance known for palladium-catalyzed reactions, an interesting selectivity was observed with functional groups that are known to react either in palladium-catalyzed reactions or reactions catalyzed by other transition-metals. Thus aryl halides, terminal alkynes, 1,6-enynes, and alpha-allenic alcohols were tolerated. In the latter example the selective reaction

  研究了末端烯基酮1到2,4-二取代的呋喃3的钯催化的环化/二聚化的范围。简化和改善的条件几乎只提供了二聚体3，仅伴有痕量的易于分离的单体2。完全抑制了3的异构体，即未共轭的酮4的形成。在这些温和的条件下，除了钯催化的反应对正常官能团的耐受性外，还发现了与已知在钯催化的反应或由其他过渡金属催化的反应中反应的官能团的有趣选择性。因此，可以耐受芳基卤化物，末端炔烃，1，6-烯炔和α-烯丙醇。在后一实例中，实现了两种不同的烯丙基中仅一种的选择性反应。
• Diastereoselective addition of organomanganese compounds to ?-alkoxysubstituted propanals
  作者：A. N. Kasatkin、R. Kh. Biktimirov、I. P. Podlipchuk、V. R. Sultanmuratova、G. A. Tolstikov

  DOI：10.1007/bf00700000

  日期：1993.1

  Reactions of organomanganese compounds R1MnI (R1 = Ph, 4-MeC6H4-, Me, Bu,n-C7H15, BuC=C, PhOC), prepared from R1Li and Mnl2 in Et2O, with aldehydes MeCH(OR2)CHO (R2 = CH2Ph, CH2OMe, CH2OCH2Ph) affordthreo-alcohols MeCH(OR2)CH(OH)R1 with high diastereoselectivity. The interactions of phenylmanganese derivatives PhMnX (X = Cl, Br, I), Ph2Mn, and Ph3MnLi with 2-benzyloxypropanal were used as examples

  由 R1Li 和 Mnl2 在 Et2O 中制备的有机锰化合物 R1MnI（R1 = Ph, 4-MeC6H4-, Me, Bu,n-C7H15, BuC=C, PhOC）与醛类 MeCH(OR2)CHO (R2 = CH2Ph, CH2OMe, CH2OCH2Ph) 提供具有高非对映选择性的苏式醇 MeCH(OR2)CH(OH)R1。以苯基锰衍生物 PhMnX（X = Cl、Br、I）、Ph2Mn 和 Ph3MnLi 与 2-苄氧基丙醛的相互作用为例，研究试剂和溶剂性质对加成非对映选择性的影响。
• MARTIN, STEPHEN F.;LI, WEI, J. ORG. CHEM., 54,(1989) N6, C. 6129-6133
  作者：MARTIN, STEPHEN F.、LI, WEI

  DOI：——

  日期：——
• TIUS M. A.; ASTRAB D. P.; GU XUE-QIN, J. ORG. CHEM., 52,(1987) N 12, 2625-2627
  作者：TIUS M. A.、 ASTRAB D. P.、 GU XUE-QIN

  DOI：——

  日期：——
• Boron trifluoride-assisted perfluoroalkylation of carbon-nitrogen double bonds
  作者：Hidemitsu Uno、Shinichiro Okada、Tetsushi Ono、Yasukazu Shiraishi、Hitomi Suzuki

  DOI：10.1021/jo00031a032

  日期：1992.2

  In the presence of BF3.OEt2, (perfluoroalkyl)lithiums generated in situ from the reaction of primary perfluoroalkyl iodides and MeLi-LiBr reacted with imines, azines, and nitrones to afford perfluoroalkylated nitrogen-containing compounds in moderate to good yields. This method was successfully applied to the preparation of a (perfluoroalkyl)glycine and optically active perfluoroalkylated amines.