| 22835-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 22835-33-2
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: MBPYUPPKESSJGW-AHUKSVIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  在 溶剂黄146 、 三乙胺 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3S,4R)-3-hydroxy-1-(4-methoxyphenyl)-4-(2-phenylethenyl)azetidin-2-one
  参考文献：
  名称：

  An efficient synthesis of enantiomerically pure 3-hydroxy-β-lactams via zinc induced removal of a chiral auxiliary

  摘要：

  The diastereoselective synthesis of various beta-lactams 6a-d and 7a-d has been achieved using a chiral acid derived from (+)-+-carene. An efficient zinc induced cleavage of the o-halo ether linkage of these beta-lactams to give enantiomerically pure 3-hydroxy-cis-beta-lactams 8a,b and 9a-d is described. (C) 2000 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0957-4166(00)00098-7
• 作为产物：
  描述：

  甲氧苯胺 、 肉桂醛 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Optically Active Aminoalcohol Promoted Addition of 2-Pyridylthioester Boron Enolates to Imines: Enantioselective One-pot Synthesis of β-Lactams

  摘要：

  The enolates derived from 2-pyridylthioesters by treatment with BCl3 . Me(2)S and enantiomerically pure aminoalcohols react with aromatic and heteroaromatic imines to afford beta-lactams in a convenient one-pot procedure and in up to 78% e.e. The aminoalcohol can be employed both as the metal ligand and as the base to generate the enolate. Among several aminoalcohols tested, N-methylephedrine turned our to be the more efficient in terms of stereoselectivity.

  DOI：

  10.1016/0040-4020(95)00503-z

文献信息

• Spiro <i>β</i>-Lactams as <i>β</i>-Turn Mimetics. Design, Synthesis, and NMR Conformational Analysis
  作者：Eduardo Alonso、Fernando López-Ortiz、Carlos del Pozo、Emma Peralta、Alberto Macías、Javier González

  DOI：10.1021/jo015714m

  日期：2001.9.1

  bonds stabilize the beta-turn conformation with a geometry that is very close to the ideal type II beta-turns. The synthesis of the spiro beta-lactams is achieved by Staudinger reaction of a cyclic ketene derived from N-bencyloxycarbonyl-L-proline acid chloride with an imine. This reaction allows the formation of the spiranic backbone in a single-step with high diastereoselectivity and good yields. The

  使用新型螺旋β-内酰胺的高级从头算方法（MP2 / 6-31 + G）进行的分子建模计算预测，这些系统可以在溶液中采用β-转二级结构。强大的分子内氢键使β-转角构象稳定，非常接近理想的II型β-转角。螺环β-内酰胺的合成通过衍生自N-苯并氧羰基-L-脯氨酸酰氯的环状烯酮与亚胺的斯陶丁格反应来实现。该反应允许单步形成芳烃骨架，具有高非对映选择性和高收率。获得的新螺-β-内酰胺类化合物是使用公认的肽化学方法制备不同类型拟肽的核心。
• Mannich-Type Reaction Promoted by an Ionic Liquid
  作者：Takahiko Akiyama、Akihiro Suzuki、Kohei Fuchibe

  DOI：10.1055/s-2005-864816

  日期：——

  The Mannich-type reaction of silyl enolates with aldimines occurred smoothly with [emim]OTf as a solvent and without the addition of an activator to afford p-amino carbonyl compounds in excellent yields.

  甲硅烷基烯醇化物与醛亚胺的曼尼希型反应以 [emim] OTf 作为溶剂顺利进行，无需添加活化剂，以优异的产率提供对氨基羰基化合物。
• A general and versatile synthesis of 3-phenylthio β-lactams as lead molecules for 3-methyl-2-azetidinones
  作者：Seema Kanwar、S. D. Sharma

  DOI：10.1002/jhet.5570440523

  日期：2007.9

  Ketene-imine cycloaddition using phosphorus oxychloride and benzenesulfonyl chloride under the described reaction conditions yielded trans 3-phenylthio 2-azetidinones in good yields. Desulfurization using Raney nickel and alkylation finally afforded trans 3-methyl-2-azetidinones in a stereoselective manner.

  在所述反应条件下，使用三氯氧化磷和苯磺酰氯的乙胺-亚胺环加成反应以良好的收率得到反式3-苯硫基2-氮杂环丁烷酮。最后使用阮内镍进行脱硫和烷基化，以立体选择性方式得到反式3-甲基-2-氮杂环丁烷酮。
• Montmorillonite K10 Catalyzed Nucleophilic Addition Reaction to Aldimines in Water
  作者：Takahiko Akiyama、Keiichiro Matsuda、Kohei Fuchibe

  DOI：10.1055/s-2005-872162

  日期：——

  Montmorillonite K10 catalyzed Mannich-type reaction and hydrophosphonylation proceeded smoothly in water at room temperature to give β-amino esters and α-amino phosphonates, respectively, in good to high yields.

  蒙脱石K10催化下的曼尼希型反应和水相膦酰化反应在室温下的水中顺利进行，分别以良好至高产率得到β-氨基酯和α-氨基膦酸盐。
• Synthesis and application of ligands for the asymmetric addition of organolithium reagents to imines
  作者：Catrin A. Jones、Iwan G. Jones、Mushtaq Mulla、Michael North、Lucia Sartori

  DOI：10.1039/a702028g

  日期：——

  Amino acid derived ligands 4d,e are prepared from (S)-valine and (S)-proline respectively, and can be used as chiral ligands during the asymmetric addition of organolithium reagents to N-arylimines. Ligand 4e, which is prepared by two independent routes, is found to induce addition of organolithium reagents to the si-face of the imines, whilst ligand 4d in common with the previously reported catalysts

  氨基酸衍生的配体4d，e分别由（S）-缬氨酸和（S）-脯氨酸制备，并且可以在将有机锂试剂不对称地添加至N-芳基胺中的过程中用作手性配体。配体4e中，它是由两个独立的途径制备，则发现诱导除了有机锂试剂的给SI亚胺的面取向，而在共同配体4d中与先前报道的催化剂4a-c中诱导除了重新的面取向亚胺。