(1'R,S)-1-(2-acetoxyphenyl)-2-propene-1-acetate | 274927-62-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (1'R,S)-1-(2-acetoxyphenyl)-2-propene-1-acetate
• 英文别名: (+/-)-1-Acetoxy-1-(2-acetoxyphenyl)-2-propene；[2-(1-acetyloxyprop-2-enyl)phenyl] acetate
• CAS: 274927-62-7
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: VHPQXBWVICRDHD-UHFFFAOYSA-N

物化性质

• 沸点：
  310.7±27.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1'R,S)-1-(2-acetoxyphenyl)-2-propene-1-acetate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 1-(o-Acetoxyphenyl)propyl acetate
  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：

  2-((tert-butyldimethylsilyl)oxy)benzaldehyde 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (1'R,S)-1-(2-acetoxyphenyl)-2-propene-1-acetate
  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

• Structure−Activity Relationships of (1‘<i>S</i>)-1‘-Acetoxychavicol Acetate, a Major Constituent of a Southeast Asian Condiment Plant <i>Languas</i> <i>galanga</i>, on the Inhibition of Tumor-Promoter-Induced Epstein−Barr Virus Activation
  作者：Akira Murakami、Kazuo Toyota、Shin Ohura、Koichi Koshimizu、Hajime Ohigashi

  DOI：10.1021/jf990528r

  日期：2000.5.1

  the terminal methylene group abolishes activity; (3) both the phenolic and alcoholic hydroxyl groups are compulsorily acetylated, and it is necessary that the former is oriented only at the position para to the side chain; (4) an additional acetoxyl group is allowed to locate at the ortho or meta position; and (5) substitution of the hydrogen atom at the 1'-position by a methyl group reduces activity

  在肿瘤启动子teleoocidin B-4诱导的爱泼斯坦-巴尔病毒（EBV）激活的抑制试验中，研究了食品来源的癌症化学预防剂（1'S）-1'-乙酸乙酰氧胆碱酯（ACA）的结构-活性关系。在拉吉细胞。通过对16种衍生物的测试，发现调节活性的结构因子如下：（1）1'-位的绝对构型不影响活性；（2）末端亚甲基的氢化消除了活性；（3）酚羟基和醇羟基均被强制乙酰化，并且前者必须仅在与侧链相对的位置上取向；（4）允许另外的乙酰氧基位于邻位或间位；（5）在1'处取代氢原子 甲基的-位置降低活性。在Raji细胞中酯酶阻断后，（1'R，S）-ACA抑制了EBV活化，其程度与对照中所测试的相同，这表明带有两个乙酰氧基的ACA是细胞内结构的活性展示的先决条件。本研究表明，对3'位置的亲核攻击很重要，并且参与了ACA与未确定的目标分子（参与EBV激活过程）的相互作用。
• Structure–activity relationships of 1′S-1′-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages
  作者：Hisashi Matsuda、Shin Ando、Toshio Morikawa、Shinya Kataoka、Masayuki Yoshikawa

  DOI：10.1016/j.bmcl.2005.01.070

  日期：2005.4

  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.