methyl 2-benzylideneaminohexanoate | 1279107-64-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-benzylideneaminohexanoate
• 英文别名: methyl 2-(benzylideneamino)hexanoate
• CAS: 1279107-64-0
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: AILONUQHDDKHQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-benzylideneaminohexanoate 在 盐酸 、 水 作用下， 生成 2-(3-Oxo-butyrylamino)-hexanoic acid methyl ester
  参考文献：
  名称：

  Synthesis and bioactivity of novel 3-(1-hydroxyethylidene)-5-substituted-pyrrolidine-2,4-dione derivatives

  摘要：

  Ten novel 5-substituted derivatives of 3-(1-hydroxyethylidene)pyrrolidine-2,4-dione were synthesized. The compounds were confirmed by IR, H-1 NMR, MS and elemental analysis. The bioassay indicated that these compounds showed noticeable herbicidal activities, and compounds 6f and 6j exhibited excellent inhibitory activities against the stalk of Echinochloa crusgalli, with EC50 values of 94.4 and 72.7 mg/L, respectively. (C) 2012 Chun Long Yang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.07.002
• 作为产物：
  描述：

  正溴丁烷 、 [(苯基甲亚基)氨基]乙酸甲酯 在 苄基三乙基氯化铵 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 methyl 2-benzylideneaminohexanoate
  参考文献：
  名称：

  Synthesis and bioactivity of novel 3-(1-hydroxyethylidene)-5-substituted-pyrrolidine-2,4-dione derivatives

  摘要：

  Ten novel 5-substituted derivatives of 3-(1-hydroxyethylidene)pyrrolidine-2,4-dione were synthesized. The compounds were confirmed by IR, H-1 NMR, MS and elemental analysis. The bioassay indicated that these compounds showed noticeable herbicidal activities, and compounds 6f and 6j exhibited excellent inhibitory activities against the stalk of Echinochloa crusgalli, with EC50 values of 94.4 and 72.7 mg/L, respectively. (C) 2012 Chun Long Yang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.07.002

文献信息

• Development of Catalytic Asymmetric 1,4-Addition and [3 + 2] Cycloaddition Reactions Using Chiral Calcium Complexes
  作者：Tetsu Tsubogo、Susumu Saito、Kazutaka Seki、Yasuhiro Yamashita、Shu̅ Kobayashi

  DOI：10.1021/ja8032058

  日期：2008.10.8

  4-addition and [3 + 2] cycloaddition reactions using chiral calcium species prepared from calcium isopropoxide and chiral bisoxazoline ligands have been developed. Glycine Schiff bases reacted with acrylic esters to afford 1,4-addition products, glutamic acid derivatives, in high yields with high enantioselectivities. During the investigation of the 1,4-addition reactions, we unexpectedly found that a [3

  已经开发了使用由异丙醇钙和手性双恶唑啉配体制备的手性钙物质的催化不对称 1,4-加成和 [3 + 2] 环加成反应。甘氨酸席夫碱与丙烯酸酯反应以高产率和高对映选择性提供 1,4-加成产物谷氨酸衍生物。在研究 1,4-加成反应期间，我们意外地发现 [3 + 2] 环加成发生在与巴豆酸酯衍生物的反应中，以高产率和高对映选择性提供取代的吡咯烷衍生物。基于这一发现，我们研究了不对称的 [3 + 2] 环加成，结果表明，获得了具有高非对映选择性和对映选择性的几种含有连续立体异构叔和季碳中心的旋光取代吡咯烷衍生物。此外，已经使用这种 [3 + 2] 环加成反应合成了丙型肝炎病毒 RNA 依赖性聚合酶抑制剂的光学活性吡咯烷核心和潜在的有效抗病毒剂。NMR 光谱分析和非线性效应实验中对映选择性的非放大观察表明，形成了具有阴离子配体的单体钙物质作为活性催化剂。提出了 [3 + 2] 环加成的逐步机制，包括 1
• Novel quaternary ammonium compounds
  申请人：Sasahara Takehiko

  公开号：US20050009805A1

  公开（公告）日：2005-01-13

  [Object] To provide a medicine useful for treatment and prevention of hyperlipidemia, further for the treatment and prevention of cholestasis-accompanying hepatopathy, particularly primary biliary cirrhosis and primary sclerosing cholangitis, and for the treatment and prevention of obesity and fatty liver. [Means] A benzothiazepine compound represented by the following formula (1), having a thioamide bond and a quaternary ammonium substituent.

  提供一种用于治疗和预防高脂血症，尤其是原发性胆汁性肝病，特别是原发性胆汁性肝硬化和原发性硬化性胆管炎，以及治疗和预防肥胖和脂肪肝的药物。代表如下式（1）的苯并噻二唑化合物，具有硫酰胺键和季铵基取代基。
• A Facile Cu(I)/BINAP-Catalyzed Asymmetric Approach to Functionalized Pyroglutamate Derivatives Bearing a Unique Quaternary Stereogenic Center
  作者：Huai-Long Teng、Fei-Long Luo、Hai-Yan Tao、Chun-Jiang Wang

  DOI：10.1021/ol202326j

  日期：2011.10.21

  pyroglutamate derivatives bearing a unique quaternary stereogenic center has been developed via Cu(I)/BINAP-catalyzed tandem Michael addition–elimination of α-substituted aldimino esters with Morita–Baylis–Hillman (MBH) carbonates followed by a deprotection/lactamization protocol, which performs well over a broad scope of substrates and provides biologically active pyroglutamate derivatives in good yields

  通过Cu（I）/ BINAP催化的串联Michael加成反应，可以直接，轻松地获得带有独特的季生立体中心的对映体富集的焦谷氨酸衍生物，然后用Morita-Baylis-Hillman（MBH）碳酸盐消除α-取代的醛糖基酯一种脱保护/内酰胺化方案，该方案在广泛的底物上表现良好，并以良好的收率和优异的对映选择性提供了具有生物活性的焦谷氨酸衍生物。
• Silver(I)-Catalyzed Atroposelective Desymmetrization of <i>N</i>-Arylmaleimide via 1,3-Dipolar Cycloaddition of Azomethine Ylides: Access to Octahydropyrrolo[3,4-<i>c</i>]pyrrole Derivatives
  作者：Hua-Chao Liu、Hai-Yan Tao、Hengjiang Cong、Chun-Jiang Wang

  DOI：10.1021/acs.joc.6b00396

  日期：2016.5.6

  has been established successfully, affording a facile access to a series of biologically important and enantioenriched octahydropyrrolo[3,4-c]pyrrole derivatives in generally high yields (up to 99%) with excellent levels of diastereo-/enantioselectivities (up to 99% ee, >20:1 dr). Subsequent transformations led to fascinating 2H-pyrrole and polysubstituted pyrrole compounds without loss of stereoselectivity

  已经成功地建立了通过原位生成的偶氮甲亚胺的1,3-偶极环加成反应的N-（2-叔丁基苯基）马来酰亚胺的高效Ag（I）催化的对位选择性脱对称，为人们提供了一系列重要的生物学上的便捷途径和对映体富集的八氢吡咯并[3,4- c ]吡咯衍生物，通常收率高（高达99％），非对映/对映选择性极好（ee高达99％，> 20：1 dr）。随后的转化导致令人着迷的2 H-吡咯和多取代的吡咯化合物，而不会失去立体选择性。生成的手性轴的绝对构型已明确标识为（M）通过单晶X射线衍射分析。此外，基于全面的实验结果和一种环加合物的绝对构型，立体选择性的起源被认为归因于手性配体和叔丁基的庞大的PPh 2基团造成的空间拥挤。N-（2-叔丁基苯基）马来酰亚胺的基团。手性配体的NH 2基团与N-（2-叔丁基苯基）马来酰亚胺的羰基之一之间可能的氢键相互作用被认为有助于稳定过渡态。
• Nickel/Copper‐Cocatalyzed Asymmetric Benzylation of Aldimine Esters for the Enantioselective Synthesis of α‐Quaternary Amino Acids
  作者：Youbin Peng、Chongyu Han、Yicong Luo、Guanlin Li、Xiaohong Huo、Wanbin Zhang

  DOI：10.1002/anie.202203448

  日期：2022.6.7

  The first Ni/Cu cocatalyzed asymmetric benzylation of aldimine esters has been developed. DFT calculations revealed that the strong electrophilicity of the η3-benzylnickel intermediate enabled the reaction to proceed smoothly under base-free conditions. The method was applied to the synthesis of BIRT-377 analogues, the key intermediate of PD154075 and CI-988.

  已经开发了第一个 Ni/Cu 共催化的醛亚胺酯的不对称苄基化。DFT计算表明，η 3 -苄基镍中间体的强亲电性使反应在无碱条件下顺利进行。该方法应用于PD154075和CI-988的关键中间体BIRT-377类似物的合成。