Acetic acid (E)-5-(tert-butyl-dimethyl-silanyloxy)-5-[5-(tert-butyl-dimethyl-silanyloxy)-2-(toluene-4-sulfonylamino)-phenyl]-pent-2-enyl ester | 409093-36-3

• 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: Acetic acid (E)-5-(tert-butyl-dimethyl-silanyloxy)-5-[5-(tert-butyl-dimethyl-silanyloxy)-2-(toluene-4-sulfonylamino)-phenyl]-pent-2-enyl ester
• 英文别名: [(E)-5-[tert-butyl(dimethyl)silyl]oxy-5-[5-[tert-butyl(dimethyl)silyl]oxy-2-[(4-methylphenyl)sulfonylamino]phenyl]pent-2-enyl] acetate
• CAS: 409093-36-3
• 化学式: C₃₂H₅₁NO₆SSi₂
• 分子量: 633.997
• InChiKey: KCQPTCMWTUMEAV-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.75
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  99.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (E)-5-(tert-butyl-dimethyl-silanyloxy)-5-[5-(tert-butyl-dimethyl-silanyloxy)-2-(toluene-4-sulfonylamino)-phenyl]-pent-2-enyl ester 在 三丁基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以92%的产率得到4,6-di-(tert-butyldimethylsiloxy)-1-(4-methylbenzenesulfonyl)-2-vinyl-1,2,3,4-tetrahydroquinoline
  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
• 作为产物：
  描述：

  5-[5-(tert-butyldimethylsiloxy)-2-(4-methylbenzenesulfonylamino)phenyl]-5-hydroxypent-2-enoic acid methyl ester 在 咪唑 、 4-二甲氨基吡啶 、 二异丁基氢化铝 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 Acetic acid (E)-5-(tert-butyl-dimethyl-silanyloxy)-5-[5-(tert-butyl-dimethyl-silanyloxy)-2-(toluene-4-sulfonylamino)-phenyl]-pent-2-enyl ester
  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

文献信息

• Concise total synthesis of flavone C-glycoside having potent anti-inflammatory activity
  作者：Takumi Furuta、Tomoyuki Kimura、Sachiko Kondo、Hisashi Mihara、Toshiyuki Wakimoto、Haruo Nukaya、Kuniro Tsuji、Kiyoshi Tanaka

  DOI：10.1016/j.tet.2004.08.015

  日期：2004.10

  The total synthesis of anti-inflammatory active flavone C-glycoside isolated from oolong tea extract is achieved. Introducing a C-glucosyl moiety to an aryl system and constructing a fused tetracyclic ring characteristic to this natural product were conducted based on the O-to-C rearrangement of sugar moiety and the successive intramolecular Mitsunobu reaction, respectively. This concise and efficient

  从乌龙茶提取物中分离得到的抗炎活性黄酮C-糖苷的总合成得以实现。一个引入Ç -glucosyl部分与芳基系统和构建稠四环特性此天然产物进行基于所述被ø -到- Ç分别糖部分和连续的分子内Mitsunobu反应，重排。这种简洁有效的合成途径适用于目标黄酮的大规模合成，也可用于构建相关化合物的大型文库。