[1-(3-Methoxy-phenyl)-meth-(E)-ylidene]-propyl-amine | 16928-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [1-(3-Methoxy-phenyl)-meth-(E)-ylidene]-propyl-amine
• 英文别名: 1-(3-methoxyphenyl)-N-propylmethanimine
• CAS: 16928-34-0
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: IQGGRDDYRSKZTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [1-(3-Methoxy-phenyl)-meth-(E)-ylidene]-propyl-amine 在 palladium diacetate 、 sodium tetrahydroborate 、 copper diacetate 、 air 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.0h， 生成 N-n-propyl-1,3-dihydro-5-methoxy-1-oxoisoindoline
  参考文献：
  名称：

  Preparation of Benzolactams by Pd(OAc)₂-Catalyzed Direct Aromatic Carbonylation

  摘要：

  We developed a new method for Pd(II)-catalyzed direct aromatic carbonylation in a phosphine-free catalytic system using Pd(OAc)2 and Cu(OAc)2 in an atmosphere of CO gas containing air. The carbonylation proceeded with ortho-palladation, inducing a remarkable site selectivity to afford a variety of five- or six-membered benzolactams from secondary omega-arylalkylamines, such as N-alkylbenzylamines or N-alkylphenethylamines.

  DOI：

  10.1021/ja045342+
• 作为产物：
  描述：

  正丙胺 、 3-甲氧基苯甲醛 在 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 以67 %的产率得到[1-(3-Methoxy-phenyl)-meth-(E)-ylidene]-propyl-amine
  参考文献：
  名称：

  烷基锌试剂的曼尼希型反应

  摘要：

  在不同条件下研究了烷基卤化锌与亚胺的加成反应。虽然与磺酰亚胺的曼尼希型反应在简单加热时发生，但使用N-烷基亚胺需要额外的活化：使用乙酰氯导致制备N-酰基叔胺，而三甲基氯硅烷可直接获得未保护的仲胺。

  DOI：

  10.1002/ejoc.202300572

文献信息

• Separation of Ring Polar and Resonance Effects on the Rate Constants for Uncatalyzed N-Arylidenepropylamine Formation in Methanol
  作者：Jean Toullec、Didier Milin

  DOI：10.1021/jo00089a033

  日期：1994.5

  Rate constants are reported for the reaction of a series of 19 ring-substituted benzaldehydes with propylamine in methanol and in O-d-methanol at different temperatures and of three of them with 2-methoxyethylamine and 2,2-dimethoxyethylamine. The large direct solvent kinetic isotope effects (KSIE) (2.1-2.9), as well as the Delta H* (4.7-7.6 kcal mol(-1)) values vary smoothly with substituent. Delta S* (ca. -45 cal mol(-1) K-1) is almost independent of substituent. These data indicate that there in no change in the rate-limiting step, and since the large KSIE and \Delta S*\ can be related to significant solvation of the leading OH- group at the transition state, they agree with a mechanism involving cu-amino alcohol formation in a fast preequilibrium followed by rate-limiting OH- detachment yielding iminium ions. When corrected for parallel hemiacetal formation, the second-order rate constants are accounted for by the Young-Jencks equation with p(n) = 0.08 and p(r) = 0.57, this equation allowing a separation of the direct resonance effects from the polar effects of the substituted ring. The very low p(n) value indicates that the polar effects for the rate-limiting OH- detachment are almost compensated by those on the constant of the alpha-amino alcohol-formation preequilibrium. In contrast, the relatively large p(r) coefficient, which means that the overall rate constants depend almost exclusively on resonance, is due to predominance of the direct resonance effects on the preequilibrium. The KSIE and Delta S* data, as well as the beta(nucl) parameters (close to unity) observed when the reacting amine was changed (slopes of the straight lines obtained by plotting the logarithm of the rate constants vs the pK(a) of the ammonium ions) favor a late transition state. In contrast, the low p(r) value for the rate-limiting step (ca. -0.5) shows that the transition state is not iminium ion-like.
• Synthesis of Novel 2-Alkoxy-3-amino-3-arylpropan-1-ols and 5-Alkoxy-4-aryl-1,3-oxazinanes with Antimalarial Activity
  作者：Matthias D’hooghe、Stijn Dekeukeleire、Karen Mollet、Carmen Lategan、Peter J. Smith、Kelly Chibale、Norbert De Kimpe

  DOI：10.1021/jm9002632

  日期：2009.7.9

  A variety of novel syn-2-alkoxy-3-amino-3-arylpropan-1-ols was prepared through LiAlH4-promoted reductive ring-opening of cis-3-alkoxy-4-aryl-beta-lactams in Et2O. The latter gamma-aminoalcohols were easily converted into cis-5-alkoxy-4-aryl-1,3-oxazinanes using formaldehyde in THE Both series of compounds were evaluated against a chloroquine sensitive strain of Plasmodium falciparum (D10), revealing micromolar potency for almost all representatives. Eleven compounds exhibited antimalarial activity with IC50 values of <= 30 mu M, and the majority of these compounds did not show cytotoxicity at the concentrations tested.
• Preparation of Benzolactams by Pd(OAc)₂-Catalyzed Direct Aromatic Carbonylation
  作者：Kazuhiko Orito、Akiyoshi Horibata、Takatoshi Nakamura、Harumi Ushito、Hideo Nagasaki、Motoki Yuguchi、Satoshi Yamashita、Masao Tokuda

  DOI：10.1021/ja045342+

  日期：2004.11.1

  We developed a new method for Pd(II)-catalyzed direct aromatic carbonylation in a phosphine-free catalytic system using Pd(OAc)2 and Cu(OAc)2 in an atmosphere of CO gas containing air. The carbonylation proceeded with ortho-palladation, inducing a remarkable site selectivity to afford a variety of five- or six-membered benzolactams from secondary omega-arylalkylamines, such as N-alkylbenzylamines or N-alkylphenethylamines.
• Mannich‐Type Reactions of Alkylzinc Reagents
  作者：Marine Pinaud、Emilie Plantiveau、Eric Huet、Erwan Le Gall、Marc Presset

  DOI：10.1002/ejoc.202300572

  日期：2023.8.21

  The addition of alkylzinc halides to imines has been studied under different conditions. Whereas Mannich-type reactions with sulfonyl imines occurs upon simple heating, the use N-alkyl imines required an additional activation: the use of acetyl chloride led to the preparation of N-acyl tertiary amines whereas trimethylsilyl chloride afforded a direct access to unprotected secondary amines.

  在不同条件下研究了烷基卤化锌与亚胺的加成反应。虽然与磺酰亚胺的曼尼希型反应在简单加热时发生，但使用N-烷基亚胺需要额外的活化：使用乙酰氯导致制备N-酰基叔胺，而三甲基氯硅烷可直接获得未保护的仲胺。