3-methoxy-benzaldehyde N-(tert-butoxycarbonyl)imine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-methoxy-benzaldehyde N-(tert-butoxycarbonyl)imine
• 英文别名: 3-methoxybenzaldehyde N-(tert-butoxycarbonyl)imine；tert-butyl 3-methoxybenzylidenecarbamate；Carbamic acid, [(3-methoxyphenyl)methylene]-, 1,1-dimethylethyl ester；tert-butyl (NE)-N-[(3-methoxyphenyl)methylidene]carbamate
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: FNINBPYNKZZGFU-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxy-benzaldehyde N-(tert-butoxycarbonyl)imine 、 丙烯基三氯硅烷 在 N,N-二甲基甲酰胺 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以86%的产率得到N-tert-butoxycarbonyl-1-(3'-methoxyphenyl)but-3-enamine
  参考文献：
  名称：

  Facile Allylation of N‐Boc and N‐Cbz Imines with Allyltrichlorosilane promoted by DMF

  摘要：

  Facile allylation of various N-Boc and N-Cbz imines with allyltrichlorosilane has been effected using N,N-dimethylformamide (DMF) as the activator. The N-Boc and N-Cbz homoallylic amines were obtained in good to high yields under mild conditions.

  DOI：

  10.1080/00397910701860422
• 作为产物：
  描述：

  氨基甲酸叔丁酯 、 3-甲氧基苯甲醛 在 甲酸 、 sodium benzenesulfonate 、 potassium carbonate 、 sodium sulfate 作用下， 以 甲醇 、 水 、 四氢呋喃 为溶剂， 反应 72.0h， 生成 3-methoxy-benzaldehyde N-(tert-butoxycarbonyl)imine
  参考文献：
  名称：

  用于Henry和Aza-Henry反应的多功能超分子铜（II）配合物

  摘要：

  Abstractmagnified imageChiral supramolecular metal‐organic frameworks assembled from copper complexes catalyse Henry and aza‐Henry reactions of aromatic and aliphatic aldehydes and N‐protected aromatic imines in high yield and good to excellent enantioselectivity. Reactions can be performed in the absence of base in ethanol or water.

  DOI：

  10.1002/adsc.200900069

文献信息

• Oxazoline-Thiourea as a Bifunctional Organocatalyst: Enantioselective aza-Henry Reactions
  作者：Yu-wei Chang、Jing-jun Yang、Jin-ning Dang、Yue-xia Xue

  DOI：10.1055/s-2007-984916

  日期：——

  Bifunctional oxazoline-thiourea-based organocatalysts were synthesized and applied to the aza-Henry reactions between N-Boc aryl imines and nitromethane in high ee and chemical yields at room temperature.

  合成了基于恶唑啉-硫脲的双功能有机催化剂，并将其应用于 N-Boc 芳基亚胺与硝基甲烷之间的 aza-Henry 反应，在室温下具有高 ee 和化学产率。
• Palladium-Catalyzed Asymmetric [3+2] Cycloaddition of Trimethylenemethane with Imines
  作者：Barry M. Trost、Steven M. Silverman、James P. Stambuli

  DOI：10.1021/ja0753389

  日期：2007.10.1

  The transition metal-catalyzed trimethylenemethane [3+2] cycloaddition provides a direct route to functionalized heterocycles. Herein, we describe a catalytic, asymmetric protocol for the reaction between 3-acetoxy-2-trimethylsilylmethyl-1-propene and various imines. The corresponding pyrrolidines were obtained in excellent yields and enantioselectivities making use of the novel phosphoramidite L10

  过渡金属催化的三亚甲基甲烷 [3+2] 环加成为功能化杂环提供了直接途径。在此，我们描述了 3-acetoxy-2-trimethylsilylmethyl-1-propene 与各种亚胺之间反应的催化、不对称协议。利用新型亚磷酰胺 L10，以优异的产率和对映选择性获得了相应的吡咯烷。
• Direct enantio- and diastereoselective Mannich reactions of malonate and β-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative
  作者：A. Louise Tillman、Jinxing Ye、Darren J. Dixon

  DOI：10.1039/b515725k

  日期：——

  A highly enantioselective Mannich reaction between malonate esters and N-Boc and N-Cbz aldimines, catalysed by a bifunctional cinchonine derivative, has been developed; extension of this methodology to encompass the use of 2-substituted-1,3-dicarbonyl nucleophiles allows the formation of adjacent stereocentres, one of which is quaternary, in high relative and absolute stereocontrol.

  已开发出由双官能辛可宁衍生物催化的丙二酸酯与N-Boc和N-Cbz Aldimines之间高度对映选择性的Mannich反应；该方法的扩展以涵盖使用2-取代的1,3-二羰基亲核试剂，可以在高度相对和绝对的立体控制下形成相邻的立体中心，其中一个是季铵盐。
• An enantioselective Brønsted acid catalyzed enamine Mannich reaction
  作者：A. Louise Tillman、Darren J. Dixon

  DOI：10.1039/b616143j

  日期：——

  An enantioselective Bronsted acid catalyzed Mannich reaction between acetophenone derived enamines and N-Boc imines has been developed. Simple diol (S)-H(8)-BINOL has been identified as the optimal catalyst, to afford versatile beta-amino aryl ketones in good yield and enantiomeric excess.

  已开发出苯乙酮衍生的烯胺和N-Boc亚胺之间的对映选择性布朗斯台德酸催化的曼尼希反应。简单的二醇（S）-H（8）-BINOL已被确定为最佳催化剂，以良好的收率和过量的对映体提供通用的β-氨基芳基酮。
• Versatile Supramolecular Copper(II) Complexes for Henry and Aza-Henry Reactions
  作者：Guoqi Zhang、Eiji Yashima、Wolf-D. Woggon

  DOI：10.1002/adsc.200900069

  日期：2009.6

  Abstractmagnified imageChiral supramolecular metal‐organic frameworks assembled from copper complexes catalyse Henry and aza‐Henry reactions of aromatic and aliphatic aldehydes and N‐protected aromatic imines in high yield and good to excellent enantioselectivity. Reactions can be performed in the absence of base in ethanol or water.