1-(2'-羟基苯基)丙-2-烯-1-醇 | 38865-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 1-(2'-羟基苯基)丙-2-烯-1-醇
• 英文名称: 2-(1-hydroxyallyl)phenol
• 英文别名: 1-(2-hydroxyphenyl)-2-propen-1-ol；2-(1-Hydroxy-2-propenyl)phenol；2-(1-hydroxyprop-2-enyl)phenol
• CAS: 38865-40-6
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: CWHOMRAMOKBXFA-UHFFFAOYSA-N

物化性质

• 沸点：
  250.3±7.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2'-羟基苯基)丙-2-烯-1-醇 在 氯[2-(二叔丁基磷)二苯基]金 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以82%的产率得到2H-色烯
  参考文献：
  名称：

  A highly adaptable catalyst/substrate system for the synthesis of substituted chromenes

  摘要：

  报道了金(I)催化的o-(1-羟基烯丙基)苯酚内环化反应以形成色烯类化合物。该标题化合物从容易获得的底物中以高产率制备。该系统能耐受富电子和缺电子的芳香环以及烯丙基部分的高程度取代。

  DOI：

  10.1039/c0cc01961e
• 作为产物：
  描述：

  2-((tert-butyldimethylsilyl)oxy)benzaldehyde 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 1-(2'-羟基苯基)丙-2-烯-1-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

文献信息

• Expanding the scope of the Babler–Dauben oxidation: 1,3-oxidative transposition of secondary allylic alcohols
  作者：Patrick M. Killoran、Steven B. Rossington、James A. Wilkinson、John A. Hadfield

  DOI：10.1016/j.tetlet.2016.07.076

  日期：2016.8

  We report the catalytic chromium-mediated oxidation of secondary allylic alcohols to give α,β-unsaturated aldehydes with exclusive (E)-stereoselectivity. This facile procedure employs catalytic PCC (5 mol %) and periodic acid (H5IO6) as a co-oxidant. This transformation occurs specifically with aromatic substituted allyl alcohols containing both electron withdrawing and electron donating substituents

  我们报告了催化铬介导的仲烯丙基醇的氧化，以产生具有排他性（E）-立体选择性的α，β-不饱和醛。该简便的方法采用了催化PCC（5 mol％）和高碘酸（H 5 IO 6）作为助氧化剂。这种转变特别发生在含有吸电子和供电子取代基以及一系列官能团的芳族取代的烯丙醇上。
• Oxygen as single oxidant for two steps: base-free one-pot Pd(<scp>ii</scp>)-catalyzed alcohol oxidation &amp; arylation to halogen-intact β-aryl α,β-enones
  作者：Mari Vellakkaran、Murugaiah M. S. Andappan、Kommu Nagaiah

  DOI：10.1039/c4ra07478e

  日期：——

  Using oxygen as the sole oxidant for two steps, we developed a new method to synthesize β-aryl α,β-enones by fine-tuning the Pd(ii)-catalyzed oxidation of allyl alcohol to subsequent arylation with arylboronic acids, arylboronic ester and aryltrifluoroborate salt.

  使用氧气作为唯一氧化剂的两步法，我们开发了一种新方法，通过微调Pd（II）催化的烯丙醇氧化反应，然后与芳基硼酸、芳基硼酯和芳基三氟硼酸盐进行芳基化反应，合成β-芳基α，β-烯酮。
• 2<i>H</i>-Chromenes Generated by an Iron(III) Complex-Catalyzed Allylic Cyclization
  作者：L. Calmus、A. Corbu、J. Cossy

  DOI：10.1002/adsc.201500058

  日期：2015.5.4

  A straightforward method based on an iron(III) complex‐catalyzed cyclization of 2‐(1‐hydroxyallyl)phenols is reported to access a large variety of 2H‐chromenes. This method was applied to the total synthesis of a natural product, tephrowatsin B.

  据报道，一种基于铁（III）络合物催化的2-（1-羟基烯丙基）苯酚环化的简单方法可以使用多种2 H-色烯。该方法应用于天然产物替弗洛韦汀B的全合成。
• Dehydrative Cross-Coupling of Allylic Alcohols with Alkynes
  作者：Peizhong Xie、Zuolian Sun、Shuangshuang Li、Lei Zhang、Xinying Cai、Weishan Fu、Xiaobo Yang、Yanan Liu、Xiangyang Wo、Teck-Peng Loh

  DOI：10.1021/acs.orglett.0c00108

  日期：2020.2.21

  the directly dehydrative cross-coupling of allylic alcohols with terminal alkynes was developed. This calcium salt cocatalyst facilitates the oxidative addition of the palladium catalyst (1 mol %) to the C-OH bond. Then, the in situ-generated hydroxide ion deprotonates the terminal alkynes to promote the formation of the allylalkynylpalladium intermediate, liberating water as the only byproduct. This

  开发了一种高效的Pd / Ca催化体系，用于烯丙基醇与末端炔烃的直接脱水交叉偶联。该钙盐助催化剂促进了钯催化剂（1mol％）向C-OH键的氧化加成。然后，原位产生的氢氧根离子使末端炔烃去质子化，从而促进烯丙基炔基钯中间体的形成，释放出水作为唯一的副产物。密度泛函理论计算也支持这种提出的机制。由便宜的起始原料以10g规模制备抗癌剂。
• 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。