3-(4-methoxyphenyl)chroman-7-ol | 10499-17-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-(4-methoxyphenyl)chroman-7-ol
• 英文别名: 4'-Methoxy-7-isoflavanol；3-(4-methoxyphenyl)-3,4-dihydro-2H-chromen-7-ol
• CAS: 10499-17-9
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: FPRFNXQLWQOWED-UHFFFAOYSA-N

物化性质

• 熔点：
  148-150 °C
• 沸点：
  418.0±45.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)chroman-7-ol 在 三氯化硼 、 四丁基碘化铵 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.66h， 以95%的产率得到雌马酚
  参考文献：
  名称：

  Processes for Preparing Isoflavonoids using 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran as a Starting Material

  摘要：

  本文披露了一种制备异黄酮类化合物的方法，特别是制备haginin E、equol、daidzein、formononetin等化合物的方法，其中7-苄氧基-3-(4-甲氧基苯基)-2H-1-苯并吡喁被用作共同的起始原料。

  公开号：

  US20100298581A1
• 作为产物：
  描述：

  刺芒柄花素 在 5%-palladium/activated carbon 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 以58%的产率得到3-(4-methoxyphenyl)chroman-7-ol
  参考文献：
  名称：

  Synthesis of Various Kinds of Isoflavones, Isoflavanes, and Biphenyl-Ketones and Their 1,1-Diphenyl-2-picrylhydrazyl Radical-Scavenging Activities

  摘要：

  合成了四十八种异黄酮（8）、三十一种异黄烷（9）以及四十七种联苯酮（10, 10′），这些化合物是由十一种取代酚（11）和六种苯乙酸（12）合成的。其中，有七十五种化合物是新发现的。这些化合物的自由基清除活性在pH 6.0下使用1,1-二苯基-2-吡唑啉酮（DPPH）进行了评估。我们发现，在四十三种含有儿茶酚基的化合物中，三十九种在A环或B环上表现出与儿茶素相似的高活性（ED50=12—54 μM）。在这些情况下，它们结构的其他部分似乎对活性影响不大。许多6-或8-羟基异黄烷（9E—I）及其联苯酮衍生物（10E—H）也显示出高活性（ED50=<50 μM），而它们对应的异黄酮（8E—I）则完全没有活性。具有在C5位增加羟基（9D）或在C6位增加甲氧基（9J）的7-羟基异黄烷则展现出高活性（ED50=26—32 μM）。本研究表明，天然异黄酮通过在C6、C8或C3′位置的羟基化，或通过代谢或生物转化形成异黄烷（9）和/或联苯酮衍生物（10′），具有表现抗氧化活性的可能性。

  DOI：

  10.1248/cpb.57.346
• 作为试剂：
  描述：

  7-Benzyloxy-4'-methoxy-Δ³-isoflaven 在 三氯化硼 、 四丁基碘化铵 、 3-(4-methoxyphenyl)chroman-7-ol 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以79%的产率得到脑益嗪
  参考文献：
  名称：

  Processes for Preparing Isoflavonoids using 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran as a Starting Material

  摘要：

  本文披露了一种制备异黄酮类化合物的方法，特别是制备haginin E、equol、daidzein、formononetin等化合物的方法，其中7-苄氧基-3-(4-甲氧基苯基)-2H-1-苯并吡喁被用作共同的起始原料。

  公开号：

  US20100298581A1

文献信息

• Some photochemical and oxidative conversions of pterocarpans and isoflavans: functional requirements for cyclization of isoflavans to pterocarpans
  作者：Jaco C. Breytenbach、Jan J. van Zyl、Pieter J. van der Merwe、Gerhardus J. H. Rall、David G. Roux

  DOI：10.1039/p19810002684

  日期：——

  9-methylenedioxy-ring system. Oxidative conversions of 2′,7-dihydroxyisoflavans to pterocarpans with 2,3-dichloro-5,6-dicyanobenzoquinone in methanol may proceed via unstable quinone methides, or via 4-carbocation intermediates after hydride abstraction. However, appropriate 2′-hydroxy-4′-methoxy-disubstitution provides the first example of selective aromatic methoxylation of the B-ring under oxidative conditions.

  翼果烷在甲醇或乙酸中的光解提供了通过C环裂变和溶剂解获得4-官能化2'-羟基-3,4-反-异黄酮的第一个通用方法，也是直接方法。自发再循环到罗汉果烷受功能依赖因素的控制，例如有效的4位碳负离子的离域作用和醌-甲基化物中间体的形成。在分离的情况下，在8，9-亚甲基二氧基环系统裂变后，通过溶剂分解也可将光还原为异黄烷或形成8-羟基-9-甲氧基甲氧基翼果烷。在甲醇中用2,3-二氯-5,6-二氰基苯并醌将2'，7-二羟基异黄酮氧化为翼果烷的方法可能是通过不稳定的醌甲基化物或通过氢化物提取后的4-碳酸化中间体。然而，合适的2'-羟基-4'-甲氧基二取代提供了在氧化条件下B环的选择性芳族甲氧基化的第一个例子。
• Design and synthesis of 3-arylbenzopyran based non-steroidal vitamin-D₃mimics as osteogenic agents
  作者：Mohd. Imran Ahmad、Dushyant Singh Raghuvanshi、Sarita Singh、Aijaz A. John、Ravi Prakash、Kripa Shankar Nainawat、Divya Singh、Shubhandra Tripathi、Ashok Sharma、Atul Gupta

  DOI：10.1039/c6md00469e

  日期：——

  27benhanced osteoblast differentiation at 1 pM in mouse calvarial osteoblast cells without inherent toxicity.

  在小鼠头盖骨成骨细胞中，1 pM浓度下增强成骨细胞分化，且无固有毒性。
• Induction of targeted osteogenesis with 3-aryl- 2H -benzopyrans and 3-aryl- 3H -benzopyrans: Novel osteogenic agents
  作者：Atul Gupta、Imran Ahmad、Jyoti Kureel、Mohammad Hasanain、Praveen Pandey、Sarita Singh、Aijaz A. John、Jayanta Sarkar、Divya Singh

  DOI：10.1016/j.jsbmb.2016.01.010

  日期：2016.4

  Development of target oriented chemotherapeutics for treatment of chronic diseases have been considered as an important approach in drug development. Following this approach, in our efforts for exploration of new osteogenic leads, substituted 3-aryl-2H-benzopyran and 3-aryl-3H-benzopyran derivatives (19, 20a-e, 21, 22a-e, 26, 27, 28a-e, 29, 31a-b, 32 and 33) have been characterized as estrogen receptor-(3 selective osteogenic (bone forming) agents. The synthesized compounds were evaluated for osteogenic activity using mouse calvarial osteoblast cells. Four compounds viz 20b, 22a, 27and 32 showed significant osteogenic activity at EC50 values 1.35, 34.5, 407 and 29.5 pM respectively. Out of these, 20b and 32 were analyzed for their bone mineralization efficacy and osteogenic gene expression by qPCR. The results showed that 20b and 32 significantly increased mineral nodule formation and the transcript levels of BMP-2, RUNX-2 and osteocalcin at 100 pM concentrations respectively. Further mechanistic studies of 20b and 32 using transiently knocked down expression of ER-alpha and beta in mouse osteoblast (MOBs) showed that 20b and 32 exerts osteogenic efficacy via activation of estrogen receptor-beta preferentially. Additionally, compounds showed significant anticancer activity in a panel of cancer cell lines within the range of (IC50) 6.54-27.79 mu M. The most active molecule, 22b inhibited proliferation of cells by inducing apoptosis and arresting cell cycle at sub-G(0) phase with concomitant decrease in cells at S phase. (C) 2016 Elsevier Ltd. All rights reserved.
• Synthesis, structure–activity relationship analysis and kinetics study of reductive derivatives of flavonoids as Helicobacter pylori urease inhibitors
  作者：Zhu-Ping Xiao、Zhi-Yun Peng、Jing-Jun Dong、Juan He、Hui Ouyang、Yu-Ting Feng、Chun-Lei Lu、Wan-Qiang Lin、Jin-Xiang Wang、Yin-Ping Xiang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2013.03.016

  日期：2013.5

  In a continuing study for discovering urease inhibitors based on flavonoids, nineteen reductive derivatives of flavonoids were synthesized and evaluated against Helicobacter pylori urease. Analysis of structure-activity relationship disclosed that 4-deoxy analogues are more potent than other reductive products. Out of them, 4',7,8-trihydroxyl-2-isoflavene (13) was found to be the most active with IC50 of 0.85 mu M, being over 20-fold more potent than the commercial available urease inhibitor, acetohydroxamic acid (AHA). Kinetics study revealed that 13 is a competitive inhibitor of H. pylori urease with a K-i value of 0.641 mu M, which is well matched with the results of molecular docking. Biological evaluation and mechanism study of 13 suggest that it is a good candidate for discovering novel anti-gastritis and anti-gastric ulcer agent. (c) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis of haginin E, equol, daidzein, and formononetin from resorcinol via an isoflavene intermediate
  作者：Sie-Rong Li、Po-Yuan Chen、Liang-Yeu Chen、Yi-Fang Lo、Ian-Lih Tsai、Eng-Chi Wang

  DOI：10.1016/j.tetlet.2009.02.159

  日期：2009.5

  New syntheses of haginin E, equol, daidzein and formononetin are described in this Letter. Through a sequence of a Wittig reaction, C-alkylation, and another Wittig reaction, 4-benzyloxysalicylaldehyde, which was prepared from resorcinol in two steps, was converted into the desired diene in one pot. Subsequently, the prepared diene was subjected to ring-closing metathesis using Grubbs' catalyst (II) to construct the desired isoflavene intermediate. Using the prepared isoflavene, certain isoflavonoids such as haginin E, equol, daidzein, fomononetin and other related compounds were derived smoothly and in good overall yields. (C) 2009 Elsevier Ltd. All rights reserved.