1-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>-1,3-butadiene | 161330-61-6

• 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: 1-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>-1,3-butadiene
• 英文别名: 2-trimethylsilylethyl N-[(1E)-buta-1,3-dienyl]carbamate
• CAS: 161330-61-6
• 化学式: C₁₀H₁₉NO₂Si
• 分子量: 213.352
• InChiKey: OZPANDKRDIZLOS-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-戊烯酸,2,3-二羰基-,1,1-二甲基乙基酯 、 1-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>-1,3-butadiene 以 苯 为溶剂， 以75%的产率得到
  参考文献：
  名称：

  邻位三羰基的化学。乙烯基和炔属衍生物在取代吲哚合成中的用途

  摘要：

  乙烯基和炔属邻位三羰基衍生物作为亲二烯体参与狄尔斯-阿尔德反应，导致取代的吲哚以及它们的二氢和四氢衍生物。

  DOI：

  10.1016/0040-4039(94)88386-6
• 作为产物：
  描述：

  2,4-戊二烯酸 、 2-(三甲硅基)乙醇 生成 1-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>-1,3-butadiene
  参考文献：
  名称：

  邻位三羰基的化学。乙烯基和炔属衍生物在取代吲哚合成中的用途

  摘要：

  乙烯基和炔属邻位三羰基衍生物作为亲二烯体参与狄尔斯-阿尔德反应，导致取代的吲哚以及它们的二氢和四氢衍生物。

  DOI：

  10.1016/0040-4039(94)88386-6

文献信息

• Chorismate-utilizing enzymes isochorismate synthase, anthranilate synthase, and p-aminobenzoate synthase: mechanistic insight through inhibitor design
  作者：Marisa C. Kozlowski、Norma J. Tom、Christopher T. Seto、Andrea M. Sefler、Paul A. Bartlett

  DOI：10.1021/ja00113a002

  日期：1995.3

  Three enzymes of the shikimic acid pathway, isochorismate synthase (IS), anthranilate synthase (AS), and p-aminobenzoate synthase (PABS), exhibit significant sequence homology and may be related mechanistically. Compounds 1, 2, and 3 were designed to mimic, in their all-axial conformations, the putative transition state for these enzymes. The inhibitors were prepared in racemic form starting from Diels-Alder addition of a propiolate ester to a protected 1-oxy- or 1-amino-1,3-butadiene in 14%, 4%, and 9%, overall yields, respectively. All three compounds are competitive inhibitors of the three enzymes, binding IS and AS strongly and PABS weakly. For both IS and AS, the affinity of the 6-amino-4-hydroxy isomer 2 is ca. 10-fold that of the 4-amino-6-hydroxy isomer 3, a difference that is largely due to their conformational equilibria; 2 is 25 +/- 2% axial and 3 is 6 +/- 3% axial, as determined by the temperature dependence of their NI?IR spectra. The similarity between IS and AS was extended by the finding that IS, like AS, catalyzes formation of 2-amino-2-deoxyisochorismate (ADIC) in the presence of ammonia. These observations are consistent with direct 1,5-substitution mechanisms for both IS and AS; the weak inhibition of PABS by these inhibitors suggests that it operates by a significantly different mechanism.
• The chemistry of vicinal tricarbonyls. Use of vinyl and acetylenic derivatives in the synthesis of substituted indoles
  作者：Harry H. Wasserman、Charles A. Blum

  DOI：10.1016/0040-4039(94)88386-6

  日期：1994.12

  Vinyl and acetylenic vicinal tricarbonyl derivatives take part as dienophiles in Diels-Alder reactions leading to substituted indoles as well as to their dihydro and tetrahydro derivatives.

  乙烯基和炔属邻位三羰基衍生物作为亲二烯体参与狄尔斯-阿尔德反应，导致取代的吲哚以及它们的二氢和四氢衍生物。