(Z)-crotonaldehyde diethyl acetal | 112775-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-crotonaldehyde diethyl acetal
• 英文别名: cis-2-buten-1-al diethyl acetal；cis-crotonaldehyde diethylacetal；cis-Crotonaldehyd-diaethylacetal；(Z)-1,1-diethoxybut-2-ene
• CAS: 112775-53-8
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: ZUMISMXLQDKQDS-DAXSKMNVSA-N

物化性质

• 沸点：
  144-146 °C(Press: 757 Torr)
• 密度：
  0.861±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-crotonaldehyde diethyl acetal 在 吡啶 、 sodium azide 、 碳酸氢钠 、 氯化铵 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 Acetic acid (1R,2S)-2-azido-1-diethoxymethyl-propyl ester
  参考文献：
  名称：

  Synergistic Inhibition of Human α-1,3-Fucosyltransferase V

  摘要：

  Human alpha-1,3-fucosyltransferase V (FucT V), which catalyzes the transfer of L-fucose moiety from guanosine diphosphate beta-L-fucose (GDP-Fuc) to an acceptor sugar To form sialyl Lewis x (sLe(x)), was shown to proceed through an ordered, sequential mechanism by product inhibition studies. The designed azatrisaccharide propyl 2-acetamido-2-deoxy-4-O-(beta-D-galactopyranosyl)-3 -O-(2-(N-(beta-L-homofuconojirimycinyl))ethyl)-alpha-D- glucopyranoside (2), prepared by covalently linking the N-group of beta-L-homofuconojirimycin (1) to the 3-OH of LacNAc through an ethylene unit, in the presence of GDP was found to be an effective inhibitor of FucT V. In the presence of 30 mu M GDP, the concentration of 2 necessary to cause 50% inhibition was reduced 77-fold to 31 mu M. Presumably, the azatrisaccharide and GDP form a complex which mimics the transition state of the enzymatic reaction. Given the low affinity of FucT V for its substrate LacNAc (K-m = 35 mM), the designed azatrisaccharide in the presence of GDP represents the most potent synergistic inhibitor complex reported so far.

  DOI：

  10.1021/ja960274f
• 作为产物：
  描述：

  2-丁炔乙缩醛 在 Pd-BaSO₄ 氢气 作用下， 生成 (Z)-crotonaldehyde diethyl acetal
  参考文献：
  名称：

  缩醛作为手性助剂，第4部分（1）：γ，δ-乙烯醛的不对称合成-加利福尼亚红级信息素的一种方法

  摘要：

  与三丁基膦结合的烯基铜-BF 3试剂与手性α，β-烯键缩醛反应立体选择性。已经制备了加利福尼亚红鳞信息素的前体。

  DOI：

  10.1016/s0040-4039(00)96125-2

文献信息

• 598. The synthesis of long-chain aliphatic acids from acetylenic compounds. Part V. The synthesis of trans-cis-herculin
  作者：R. A. Raphael、Franz Sondheimer

  DOI：10.1039/jr9510002693

  日期：——
• MANGENEY, P.;ALEXAKIS, A.;NORMANT, J. F., TETRAHEDRON LETT., 28,(1987) N 21, 2363-2366
  作者：MANGENEY, P.、ALEXAKIS, A.、NORMANT, J. F.

  DOI：——

  日期：——
• Acetals as chiral auxillaries Part 4 (1)
  作者：P. Mangeney、A. Alexakis、J.F. Normant

  DOI：10.1016/s0040-4039(00)96125-2

  日期：——

  Alkenyl copper - BF3 reagents, associated with tributylphosphine, react stereoselectivity with chiral α,β-ethylenic acetals. A precursor of the California Red scale pheromone has been prepared.

  与三丁基膦结合的烯基铜-BF 3试剂与手性α，β-烯键缩醛反应立体选择性。已经制备了加利福尼亚红鳞信息素的前体。
• Synergistic Inhibition of Human α-1,3-Fucosyltransferase V
  作者：Lei Qiao、Brion W. Murray、Makoto Shimazaki、Jody Schultz、Chi-Huey Wong

  DOI：10.1021/ja960274f

  日期：1996.1.1

  Human alpha-1,3-fucosyltransferase V (FucT V), which catalyzes the transfer of L-fucose moiety from guanosine diphosphate beta-L-fucose (GDP-Fuc) to an acceptor sugar To form sialyl Lewis x (sLe(x)), was shown to proceed through an ordered, sequential mechanism by product inhibition studies. The designed azatrisaccharide propyl 2-acetamido-2-deoxy-4-O-(beta-D-galactopyranosyl)-3 -O-(2-(N-(beta-L-homofuconojirimycinyl))ethyl)-alpha-D- glucopyranoside (2), prepared by covalently linking the N-group of beta-L-homofuconojirimycin (1) to the 3-OH of LacNAc through an ethylene unit, in the presence of GDP was found to be an effective inhibitor of FucT V. In the presence of 30 mu M GDP, the concentration of 2 necessary to cause 50% inhibition was reduced 77-fold to 31 mu M. Presumably, the azatrisaccharide and GDP form a complex which mimics the transition state of the enzymatic reaction. Given the low affinity of FucT V for its substrate LacNAc (K-m = 35 mM), the designed azatrisaccharide in the presence of GDP represents the most potent synergistic inhibitor complex reported so far.