1-(4-tert-butyldimethylsilyloxyphenyl)but-3-en-1-ol | 405081-73-4

• 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: 1-(4-tert-butyldimethylsilyloxyphenyl)but-3-en-1-ol
• CAS: 405081-73-4
• 化学式: C₁₆H₂₆O₂Si
• 分子量: 278.467
• InChiKey: OATKCJFFBGVINI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(4-tert-butyldimethylsilyloxyphenyl)but-3-en-1-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 1-(4-羟基苯基)-3-丁烯醇
  参考文献：
  名称：

  Structure–activity relationships of 1′S-1′-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages

  摘要：

  1'S-1'-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC50 value of 2.3 mu M. To clarify the structure-activity relationship of 1'S-1'-acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic phenylbutanoids were examined, and the following structural requirements were clarified. (1) The para or ortho substitution of the acetoxyl and 1-acetoxypropenyl groups at the benzene ring was essential. (2) The S configuration of the 1'-acetoxyl group was preferable. (3) The presence of the 3-methoxyl group and disappearance of the 2'-3' double bond by hydrogenation reduced the activity. (4) The substitution of acetyl groups with propionyl or methyl groups reduced the activity. (5) Lengthening of the carbon chain between the 1'- and 2'-positions reduced the activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.070
• 作为产物：
  描述：

  4-[(叔-丁基二甲基甲硅烷)氧代]苯甲醛 、 烯丙基溴化镁 以 四氢呋喃 为溶剂， 生成 1-(4-tert-butyldimethylsilyloxyphenyl)but-3-en-1-ol
  参考文献：
  名称：

  Structure–activity relationships of 1′S-1′-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages

  摘要：

  1'S-1'-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC50 value of 2.3 mu M. To clarify the structure-activity relationship of 1'S-1'-acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic phenylbutanoids were examined, and the following structural requirements were clarified. (1) The para or ortho substitution of the acetoxyl and 1-acetoxypropenyl groups at the benzene ring was essential. (2) The S configuration of the 1'-acetoxyl group was preferable. (3) The presence of the 3-methoxyl group and disappearance of the 2'-3' double bond by hydrogenation reduced the activity. (4) The substitution of acetyl groups with propionyl or methyl groups reduced the activity. (5) Lengthening of the carbon chain between the 1'- and 2'-positions reduced the activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.070

文献信息

• Total synthesis of selaginellin A
  作者：Kenshu Fujiwara、Takaya Itagaki、Tetsuo Tokiwano

  DOI：10.1016/j.tetlet.2021.153295

  日期：2021.8

  The total synthesis of selaginellin A, isolated from Selaginella tamariscina, was achieved through an eight-step process including a Diels-Alder reaction, formation of a quinone methide moiety and dehydrogenative aromatization. The NMR spectra collected for different samples of synthetic selaginellin A initially showed irregular peak shapes and variable chemical shifts for the signals of the phenol-substituted

  从tamariscina 中分离出的 selaginellin A 的全合成是通过八步过程实现的，包括 Diels-Alder 反应、醌甲基化物部分的形成和脱氢芳构化。为合成海卷胶 A 的不同样品收集的 NMR 光谱最初显示出在中性条件下苯酚取代的醌甲基化物部分的信号的不规则峰形和可变的化学位移。经过详细的核磁共振分析，发现微量三氟乙酸的加入加速了苯酚取代的醌甲基化物部分的互变异构，并提高了合成海桐素 A 化学位移的重现性。
• Rapid synthesis of homoallylic alcohol from aldehyde with allyltributylstannane under solvent-free conditions
  作者：Pranjal P. Bora、H. Atoholi Sema、Barisha Wahlang、Ghanashyam Bez

  DOI：10.1139/v11-138

  日期：2012.2

  A catalytic amount (2 mol %) of phosphotungstic acid (PTA) is sufficient to synthesize homoallylic alcohol in excellent yields from aldehyde with allyltributylstannane upon grinding under solvent-free reaction conditions. Easy handling, very short reaction time, solvent-free reaction conditions, and aqueous workup free isolation protocol may make our method very useful for synthetic chemists.

  添加2 mol％的磷钨酸（PTA）催化剂足以在无溶剂反应条件下通过研磨从醛中与烯丙基三丁基锡合成高产率的同烯丙醇。易于操作，反应时间非常短，无溶剂反应条件和无水工作提取方案可能使我们的方法对合成化学家非常有用。