N-[4-[tert-butyl(dimethyl)silyl]oxy-2-formylphenyl]-4-methylbenzenesulfonamide | 409093-33-0

• 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: N-[4-[tert-butyl(dimethyl)silyl]oxy-2-formylphenyl]-4-methylbenzenesulfonamide
• CAS: 409093-33-0
• 化学式: C₂₀H₂₇NO₄SSi
• 分子量: 405.59
• InChiKey: VJRDPMYTDSJGOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[4-[tert-butyl(dimethyl)silyl]oxy-2-formylphenyl]-4-methylbenzenesulfonamide 在 咪唑 、 碘 、 二异丁基氢化铝 、 锌 作用下， 以 乙醚 、 苯 为溶剂， 生成 N-{4-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-1-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-pent-3-enyl]-phenyl}-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  Asymmetric Synthesis of Tetrahydroquinoline Derivative, a Building Block of Martinellines, via Intramolecular Allylic Amination Using 9-PBN

  摘要：

  A tetrahydroquinoline derivative, a core structure of martinellines, was prepared through intramolecular allylic amination of the racemic precursor with a stereogenic center using 9-PBN and palladium. The reaction proceeded in a reagent-controlled manner based on the chiral phosphine to give two diastereomeric products with moderate enantioselectivities.

  DOI：

  10.3987/com-01-s(k)46
• 作为产物：
  描述：

  2-氨基-5-羟基苯甲酸甲基 在 吡啶 、 咪唑 、 重铬酸吡啶 、 锂硼氢 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-[4-[tert-butyl(dimethyl)silyl]oxy-2-formylphenyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Synthetic studies on bradykinin antagonist martinellines: construction of a pyrrolo[3,2-c]quinoline skeleton using silicon-tether RCM reaction and allylic amination

  摘要：

  The pyrrolo[3,2-c]quinoline consisting of a core structure of martinellines, the first naturally occurring heterocycle, was prepared through silicon-tether ring-closing metathesis reaction and intramolecular allylic amination as key steps. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.014

文献信息

• Scandium-Catalyzed Cascade Cyclization to Produce Cyclobutane-Fused Tetrahydroquinoline, Chromane, Thiochromane, and Tetrahydronaphthalene Derivatives
  作者：Shun-ichi Nakano、Kazumi Kakugawa、Tetsuhiro Nemoto、Yasumasa Hamada

  DOI：10.1002/adsc.201400020

  日期：2014.6.16

  We have succeeded in the highly diastereoselective synthesis of cyclobutane‐fused multi‐cyclic compounds using a scandium‐catalyzed cascade cyclization. Using 3–10 mol% of scandium(III) triflate [Sc(OTf)3], various cyclobutane‐fused tetrahydroquinoline derivatives as well as its chromane, thiochromane, and tetrahydronaphthalene analogues were obtained in good to excellent yields. Derivatizations of

  我们已经通过scan催化的级联环化成功地完成了非对映选择性的环丁烷稠合多环化合物的合成。使用3-10 mol％的三氟甲磺酸（[Sc（OTf）3 ]，可以良好的收率获得各种环丁烷稠合的四氢喹啉衍生物，以及其色烷，硫代苯并四氢萘类似物。还讨论了反应产物的衍生化以及合理的反应机理。
• Synthetic studies on bradykinin antagonist martinellines: construction of a pyrrolo[3,2-c]quinoline skeleton using silicon-tether RCM reaction and allylic amination
  作者：Osamu Hara、Kazuhiko Sugimoto、Yasumasa Hamada

  DOI：10.1016/j.tet.2004.08.014

  日期：2004.10

  The pyrrolo[3,2-c]quinoline consisting of a core structure of martinellines, the first naturally occurring heterocycle, was prepared through silicon-tether ring-closing metathesis reaction and intramolecular allylic amination as key steps. (C) 2004 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis of Tetrahydroquinoline Derivative, a Building Block of Martinellines, via Intramolecular Allylic Amination Using 9-PBN
  作者：Yasumasa Hamada、Iyo Kunimune、Osamu Hara

  DOI：10.3987/com-01-s(k)46

  日期：——

  A tetrahydroquinoline derivative, a core structure of martinellines, was prepared through intramolecular allylic amination of the racemic precursor with a stereogenic center using 9-PBN and palladium. The reaction proceeded in a reagent-controlled manner based on the chiral phosphine to give two diastereomeric products with moderate enantioselectivities.