1-(2-propenyloxy)-3,5-dihydroxybenzene | 813414-06-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(2-propenyloxy)-3,5-dihydroxybenzene
• 英文别名: allyl 3,5-dihydroxyphenyl ether；1,3-dihydroxy-5-(1-propenyl)oxybenzene；1,3-Benzenediol, 5-(2-propenyloxy)-；5-prop-2-enoxybenzene-1,3-diol
• CAS: 813414-06-1
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: KZWFZWQPOXILJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-propenyloxy)-3,5-dihydroxybenzene 在 5%-palladium/activated carbon 、 氢气 、 caesium carbonate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  固有手性四恶唑醇[2]芳烃[2]吡啶的合成与功能化

  摘要：

  通过间苯二酚衍生物与2,6-二氯-3-硝基吡啶的间苯二酚衍生物的大环缩合反应，通过一锅法有效地合成了具有C 2对称性的内在手性四氧杂碳六氢呋喃[2]芳烃。通过逐步片段偶联方法以高收率制备了具有ABCD取代模式的[2]吡啶。宏观环化后的化学操作导致功能化的四氧杂acalix [2]芳烃[2]吡啶。将外消旋体样品拆分为对映体（+）-和（-）固有的手性化合物。

  DOI：

  10.1021/ol303019q
• 作为产物：
  描述：

  间苯三酚 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到1-(2-propenyloxy)-3,5-dihydroxybenzene
  参考文献：
  名称：

  Antiprotozoal and antimicrobial activities of O-alkylated and formylated acylphloroglucinols

  摘要：

  In the present article, we examined the antileishmanial, antimalarial, antibacterial, and antifungal activities of several newly synthesized O-alkylated phloroglucinol compounds (11-19) which are analogues of the naturally occurring antimalarial compound 1. Analogues 12 and 16 exhibited antileishmanial activity against, Leishmania donovani promastigotes with IC(50)s of 5.3 and 4.2 mu g/mL, respectively. Naturally occurring monomeric formylated acylphloroglucinol compounds, grandinol (2), jensenone (3), and their analogues (29-37), were also synthesized and evaluated for antileishmanial, antimalarial, antibacterial, and antifungal activities. Amongst these, both grandinol and jensenone showed mild to moderate antibacterial, antifungal, and antileishmanial activities. Jensenone (3) was effective against Candida albicans with an IC50 of 5.5 mu g/mL but was ineffective against Cryptococcus neoformans and methicillin-resistant Staphylococcus aureus. Among the analogues, 34 was the most active against C albicans and C. neoformans with IC(50)s of 2.0 and 2.5 mu g/mL, respectively, and was fungicidal toward Candida albicans. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.006

文献信息

• Zinc-catalyzed Williamson ether synthesis in the absence of base
  作者：Satya Paul、Monika Gupta

  DOI：10.1016/j.tetlet.2004.10.009

  日期：2004.11

  Zinc powder was found to be a highly efficient catalyst for the synthesis of aromatic ethers using microwave heating in the presence of N,N-dimethylformamide as well as under stirring in an oil-bath using tetrahydrofuran as solvent without any inorganic base. This method can be used for selective mono-, di- or tri-O-alkylations. (C) 2004 Elsevier Ltd. All rights reserved.
• US8829082B2
  申请人：——

  公开号：US8829082B2

  公开（公告）日：2014-09-09
• CN117126170
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and Functionalization of Inherently Chiral Tetraoxacalix[2]arene[2]pyridines
  作者：Shuai Pan、De-Xian Wang、Liang Zhao、Mei-Xiang Wang

  DOI：10.1021/ol303019q

  日期：2012.12.21

  Inherently chiral tetraoxacalix[2]arene[2]pyridines containing C2 symmetry were synthesized efficiently from a macrocyclic condensation reaction of resorcinol derivatives with 2,6-dichloro-3-nitropyridine in a one-pot reaction manner, while tetraoxacalix[2]arene[2]pyridine with an ABCD-substitution pattern was prepared in a good yield by means of a stepwise fragment coupling approach. Postmacrocyclization

  通过间苯二酚衍生物与2,6-二氯-3-硝基吡啶的间苯二酚衍生物的大环缩合反应，通过一锅法有效地合成了具有C 2对称性的内在手性四氧杂碳六氢呋喃[2]芳烃。通过逐步片段偶联方法以高收率制备了具有ABCD取代模式的[2]吡啶。宏观环化后的化学操作导致功能化的四氧杂acalix [2]芳烃[2]吡啶。将外消旋体样品拆分为对映体（+）-和（-）固有的手性化合物。
• Antiprotozoal and antimicrobial activities of O-alkylated and formylated acylphloroglucinols
  作者：Sandip B. Bharate、Shabana I. Khan、Nafees A.M. Yunus、Siddheshwar K. Chauthe、Melissa R. Jacob、Babu L. Tekwani、Ikhlas A. Khan、Inder Pal Singh

  DOI：10.1016/j.bmc.2006.10.006

  日期：2007.1.1

  In the present article, we examined the antileishmanial, antimalarial, antibacterial, and antifungal activities of several newly synthesized O-alkylated phloroglucinol compounds (11-19) which are analogues of the naturally occurring antimalarial compound 1. Analogues 12 and 16 exhibited antileishmanial activity against, Leishmania donovani promastigotes with IC(50)s of 5.3 and 4.2 mu g/mL, respectively. Naturally occurring monomeric formylated acylphloroglucinol compounds, grandinol (2), jensenone (3), and their analogues (29-37), were also synthesized and evaluated for antileishmanial, antimalarial, antibacterial, and antifungal activities. Amongst these, both grandinol and jensenone showed mild to moderate antibacterial, antifungal, and antileishmanial activities. Jensenone (3) was effective against Candida albicans with an IC50 of 5.5 mu g/mL but was ineffective against Cryptococcus neoformans and methicillin-resistant Staphylococcus aureus. Among the analogues, 34 was the most active against C albicans and C. neoformans with IC(50)s of 2.0 and 2.5 mu g/mL, respectively, and was fungicidal toward Candida albicans. (c) 2006 Elsevier Ltd. All rights reserved.