ethyl 4-(4-methoxyphenyl)-2-(tosylimino)but-3-enoate | 1186416-07-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-(4-methoxyphenyl)-2-(tosylimino)but-3-enoate
• CAS: 1186416-07-8
• 化学式: C₂₀H₂₁NO₅S
• 分子量: 387.456
• InChiKey: PCAQYBQONQXLRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.03
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-methoxyphenyl)-2-(tosylimino)but-3-enoate 、 3-(3,4-二甲氧基-苯基)-丙醛 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 苯甲酸 作用下， 以 水 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Organocatalytic Sequential Hetero-Diels–Alder and Friedel–Crafts Reaction: Constructions of Fused Heterocycles with Scaffold Diversity

  摘要：

  A highly enantioselective aza-Diels-Alder and Friedel-Crafts reaction sequence of N-sulfonyl-1-aza-1,3-butadienes and aliphatic aldehydes tethered to an arene motif has been developed, affording the fused chiral piperidine frameworks with a versatile scaffold diversity. A similar strategy has been applied for the construction of complex chiral tetrahydroquinoxaline structures.

  DOI：

  10.1021/ol202492x

文献信息

• Enantioselective construction of lactone[2,3-b]piperidine skeletons via organocatalytic tandem reactions
  作者：Zhao-Quan He、Bo Han、Rui Li、Li Wu、Ying-Chun Chen

  DOI：10.1039/b922053d

  日期：——

  A highly enantioselective construction of δ- and γ-lactone[2,3-b]piperidine skeletons was accomplished by tandem aza-Diels–Alder reaction–hemiacetal formation–oxidation from N-Tos-1-aza-1,3-butadienes and aliphatic dialdehydes.

  δ-和的高度对映选择性 γ-内酯[2,3- b ]哌啶通过串联氮杂-狄尔斯-阿尔德反应-半缩醛形成-N -Tos-1-氮杂-1,3-丁二烯和脂肪族二醛的氧化来完成骨架。
• Enantioselective [3 + 2] annulation of α-substituted allenoates with β,γ-unsaturated <i>N</i>-sulfonylimines catalyzed by a bifunctional dipeptide phosphine
  作者：Huanzhen Ni、Weijun Yao、Yixin Lu

  DOI：10.3762/bjoc.12.37

  日期：——

  The first enantioselective [3 + 2] annulation of alpha-substituted allenoates with beta,gamma-unsaturated N-sulfonylimines is described. In the presence of a dipeptide phosphine catalyst, a wide range of highly functionalized cyclopentenes bearing an all-carbon quaternary center were obtained in moderate to good yields and with good to excellent enantioselectivities.

  描述了α-取代的烯酸酯与β，γ-不饱和N-磺酰亚胺的第一次对映选择性[3 + 2]环。在二肽膦催化剂的存在下，以中等至良好的产率以及良好至优异的对映选择性获得了带有全碳季中心的多种高度官能化的环戊烯。
• One-pot, highly efficient, asymmetric synthesis of ring-fused piperidine derivatives bearing N,O- or N,N-acetal moieties
  作者：Ji-Yao Li、Zhi-Long Li、Wei-Wei Zhao、Yan-Kai Liu、Zhi-Ping Tong、Rui Tan

  DOI：10.1039/c5ob02571k

  日期：——

  successfully expand the application of lactols or cyclic hemiaminals as nucleophiles for the asymmetric synthesis of both N,O- and N,N-acetal moieties contained in the structure of ring-fused piperidine derivatives. This efficient one-pot protocol involves an organocatalyzed asymmetric aza-Diels–Alder reaction and iminium ion induced cyclization sequence to ultimately deliver heterocyclic compounds with excellent

  我们成功地扩大了内酯或环状半缩醛作为亲核试剂的应用，用于不对称合成环稠合哌啶衍生物结构中包含的N，O和N，N-乙缩醛部分。这种有效的一锅操作方案涉及有机催化的不对称aza-Diels-Alder反应和亚胺离子诱导的环化序列，最终以高收率提供具有优异立体选择性的杂环化合物，该化合物包含三个连续的立体中心。
• E,Z-Stereodivergent synthesis of N-tosyl α,β-dehydroamino esters via a Mukaiyama–Michael addition
  作者：Miguel Espinosa、Andrea García-Ortiz、Gonzalo Blay、Luz Cardona、M. Carmen Muñoz、José R. Pedro

  DOI：10.1039/c5ra27354d

  日期：——

  The stereodivergent synthesis of N-tosyl α,β-dehydroamino esters via a Mukaiyama–Michael addition is reported. The reaction of silylketene acetals with N-tosylimines derived from β,γ-unsaturated α-keto esters in dichloromethane provided the corresponding (Z)-α,β-dehydroamino esters while the (E)-isomers were obtained when the reaction was carried out in the presence of 10 mol% copper(II) triflate.

  据报道，通过Mukaiyama-Michael加成立体合成N-甲苯磺酰基α，β-脱氢氨基酯。甲硅烷基乙烯酮缩醛与β，γ-不饱和α-酮酸酯衍生的N-甲苯磺胺在二氯甲烷中的反应提供了相应的（Z）-α，β-脱氢氨基酯，而在进行反应时获得了（E）-异构体在10mol％的三氟甲磺酸铜（II）存在下。
• Lanthanum-pyBOX complexes as catalysts for the enantioselective conjugate addition of malonate esters to β,γ-unsaturated α-ketimino esters
  作者：Miguel Espinosa、Gonzalo Blay、Luz Cardona、Isabel Fernández、M. Carmen Muñoz、Jose R. Pedro

  DOI：10.1080/00958972.2018.1437422

  日期：2018.3.19

  Abstract In this paper, we report the application of chiral complexes of La(III) with pyBOX ligands as Lewis acid catalysts in the conjugate addition of malonic esters to N-tosyl imines derived from β,γ-unsaturated α-keto esters to give the corresponding chiral α,β-dehydroamino esters. pyBOX complexes with La(III), Yb(III), Sc(III), and In(III) triflates were assessed in this reaction but only La(III)

  摘要 在本文中，我们报道了 La(III) 与 pyBOX 配体的手性配合物作为路易斯酸催化剂在丙二酸酯与 β,γ-不饱和 α-酮酯衍生的 N-甲苯磺酰亚胺的共轭加成中的应用。相应的手性α,β-脱氢氨基酯。在该反应中评估了与 La(III)、Yb(III)、Sc(III) 和 In(III) 三氟甲磺酸盐的 pyBOX 配合物，但只有 La(III) 表现出良好的活性和对映选择性，而 Yb(III) 提供了预期的产物收率和立体选择性低，Sc(III) 和 In(III) 配合物完全失活。La(OTf)3 与原位制备的二苯基-pyBOX 配体的复合物提供了最好的结果，并允许以优异的产率获得手性 α,β-脱氢氨基酯 3，E:Z 非对映体比率 (29:71–99:1)和高对映体过量（20-95%）。尽管芳环上吸电子基团的存在不利于立体选择性，但该反应可应用于具有取代的芳环或杂环连接到双键的亚胺。