2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-hexanoic acid methyl ester | 134915-78-9

• 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: 2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-hexanoic acid methyl ester
• 英文别名: Methyl 2-[(4-chlorophenyl)methylideneamino]hexanoate；methyl 2-[(4-chlorophenyl)methylideneamino]hexanoate
• CAS: 134915-78-9
• 化学式: C₁₄H₁₈ClNO₂
• 分子量: 267.755
• InChiKey: XSYQSDYVJOZXGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 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：

  2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-hexanoic acid methyl ester 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 methyl 5-butyl-2-[2-(1H-indol-3-yl)-1-(phenylmethoxycarbonylamino)ethyl]-1,4-dihydroimidazole-5-carboxylate
  参考文献：
  名称：

  Amide bond replacements : incorporation of a 2,5,5-trisubstituted imidazoline into dipeptides and into a CCK-4 derivative.

  摘要：

  Synthetic methodology for the introduction of a 2,5,5-trisubstituted imidazoline ring as an amide replacement into dipeptide derivatives of Phe, Trp, Lys (N-epsilon-CBZ) and Nle is described. This replacement is also incorporated into the Trp-Nle bond of the tetrapeptide CCK-4 derivative Trp-Nle-Asp-Phe-NH2 and the pentagastrin derivative Gly-Trp-Nle-Asp-Phe-NH2.

  DOI：

  10.1016/s0040-4039(00)79701-2
• 作为产物：
  描述：

  4-氯苯甲醛 、 DL-己氨酸甲基酯盐酸 在 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-hexanoic acid methyl ester
  参考文献：
  名称：

  Amide bond replacements : incorporation of a 2,5,5-trisubstituted imidazoline into dipeptides and into a CCK-4 derivative.

  摘要：

  Synthetic methodology for the introduction of a 2,5,5-trisubstituted imidazoline ring as an amide replacement into dipeptide derivatives of Phe, Trp, Lys (N-epsilon-CBZ) and Nle is described. This replacement is also incorporated into the Trp-Nle bond of the tetrapeptide CCK-4 derivative Trp-Nle-Asp-Phe-NH2 and the pentagastrin derivative Gly-Trp-Nle-Asp-Phe-NH2.

  DOI：

  10.1016/s0040-4039(00)79701-2

文献信息

• Synergistic Cu/Pd Catalysis for Enantioselective Allylic Alkylation of Aldimine Esters: Access to α,α-Disubstituted α-Amino Acids
  作者：Liang Wei、Shi-Ming Xu、Qiao Zhu、Chao Che、Chun-Jiang Wang

  DOI：10.1002/anie.201707019

  日期：2017.9.25

  Double duty: An enantioselective allylic alkylation of aldimine esters has been developed by using a synergistic Cu/Pd catalyst system. This strategy provides access to nonproteinogenic α,α-disubstituted α-amino acids in high yield with excellent enantioselectivity. The more challenging double allylic alkylation of glycinate-derived imine esters was also be realized. LG=leaving group.

  双重职责：通过使用协同的Cu / Pd催化剂体系，开发了醛亚胺酯的对映选择性烯丙基烷基化反应。该策略提供了以优异的对映选择性高产率获得非蛋白原性的α，α-二取代的α-氨基酸的途径。还实现了更具挑战性的甘氨酸衍生的亚胺酯的双烯丙基烷基化。LG =离开小组。
• Catalytic Asymmetric Benzylation of Azomethine Ylides Enabled by Synergistic Lewis Acid/Palladium Catalysis
  作者：Xin Chang、Jing-Di Ran、Xue-Tao Liu、Chun-Jiang Wang

  DOI：10.1021/acs.orglett.2c00865

  日期：2022.4.8

  synergistic chiral Lewis acid/achiral Pd catalyst system was successfully applied in the enantioselective benzylation of various imine esters, giving a range of α-benzyl-substituted α-amino acid derivatives in satisfactory yield with excellent enantioselectivity. It is worth noting that this strategy exhibits good tolerance for bicyclic and monocyclic benzylic electrophiles. Furthermore, the utility of this

  协同手性路易斯酸/非手性钯催化剂体系成功应用于各种亚胺酯的对映选择性苄基化反应，得到一系列α-苄基取代的α-氨基酸衍生物，收率令人满意，对映选择性优异。值得注意的是，该策略对双环和单环苄基亲电试剂具有良好的耐受性。此外，通过方便制备对映体富集的抗高血压药物 α-甲基-l-多巴，证明了该合成方案的实用性。
• Cooperative Catalyst‐Enabled Regio‐ and Stereodivergent Synthesis of α‐Quaternary α‐Amino Acids via Asymmetric Allylic Alkylation of Aldimine Esters with Racemic Allylic Alcohols
  作者：Lu Xiao、Xin Chang、Hui Xu、Qi Xiong、Yanfeng Dang、Chun‐Jiang Wang

  DOI：10.1002/anie.202212948

  日期：2022.11.14

  The regio- and stereodivergent asymmetric α-allylation of aldimine esters with racemic allylic alcohols was enabled by cooperative catalysis. The Et3B additive plays a significant role in ionizing allylic alcohols to form electrophilic metal-π-allyl species and simultaneously promotes the formation of nucleophilic Cu-ylides. Computational mechanistic studies revealed the role of the Et3B additive and

  醛亚胺酯与外消旋烯丙醇的区域和立体发散不对称 α-烯丙基化反应是通过协同催化实现的。Et 3 B 添加剂在电离烯丙醇以形成亲电子金属-π-烯丙基物质方面发挥重要作用，同时促进亲核铜叶立德的形成。计算机理研究揭示了 Et 3 B 添加剂的作用以及立体选择性和区域选择性的起源。
• Amide bond replacements : incorporation of a 2,5,5-trisubstituted imidazoline into dipeptides and into a CCK-4 derivative.
  作者：Ian Gilbert、David C. Rees、Reginald S. Richardson

  DOI：10.1016/s0040-4039(00)79701-2

  日期：1991.5

  Synthetic methodology for the introduction of a 2,5,5-trisubstituted imidazoline ring as an amide replacement into dipeptide derivatives of Phe, Trp, Lys (N-epsilon-CBZ) and Nle is described. This replacement is also incorporated into the Trp-Nle bond of the tetrapeptide CCK-4 derivative Trp-Nle-Asp-Phe-NH2 and the pentagastrin derivative Gly-Trp-Nle-Asp-Phe-NH2.