1-(苄氧基)-4-乙炔基-2-甲氧基苯 | 144735-54-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(苄氧基)-4-乙炔基-2-甲氧基苯
• 英文名称: 1-(benzyloxy)-4-ethynyl-2-methoxybenzene
• 英文别名: 1-ethynyl-4-(benzyloxy)-3-methoxybenzene；4-(benzyloxy)-3-methoxyphenylacetylene；4-benzyloxy-3-methoxyphenylacetylene；[3-methoxy-4-(benzyloxy)phenyl]acetylene；4-ethynyl-2-methoxy-1-phenylmethoxybenzene
• CAS: 144735-54-6
• 化学式: C₁₆H₁₄O₂
• mdl: MFCD08703513
• 分子量: 238.286
• InChiKey: PLUHQGRVJMSIDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(苄氧基)-4-乙炔基-2-甲氧基苯 在 palladium on activated charcoal 吡啶 、 盐酸 、 ammonium hydroxide 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 potassium chloride 、 盐酸羟胺 、 氢气 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 58.0h， 生成 5-(3-hydroxypropyl)-7-methoxy-3-methyl-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran
  参考文献：
  名称：

  Compounds from Danshen. Part 7. Regioselective introduction of carbon-3 substituents to 5-alkyl-7-methoxy-2-phenylbenzo[b]furans: synthesis of a novel adenosine A1 receptor ligand and its derivatives

  摘要：

  By maintaining the balance between the electronic requirements, the stereochemical restrictions as well as the kinetic and thermodynamic factors, the unprecedented regioselective electrophilic aromatic substitution of formyl and nitro groups to carbon-3 of 5-alkyl-7-methoxy-2-phenylbenzo[b]furans have been achieved. Subsequent transformation of the resulting formyl group into methyl, hydroxymethyl, 1-hydroxyethyl, and cyano groups are also described.

  DOI：

  10.1021/jo00052a046
• 作为产物：
  描述：

  香草乙酮 在 sodium hydroxide 、 四丁基碘化铵 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 22.33h， 生成 1-(苄氧基)-4-乙炔基-2-甲氧基苯
  参考文献：
  名称：

  Compounds from Danshen. Part 7. Regioselective introduction of carbon-3 substituents to 5-alkyl-7-methoxy-2-phenylbenzo[b]furans: synthesis of a novel adenosine A1 receptor ligand and its derivatives

  摘要：

  By maintaining the balance between the electronic requirements, the stereochemical restrictions as well as the kinetic and thermodynamic factors, the unprecedented regioselective electrophilic aromatic substitution of formyl and nitro groups to carbon-3 of 5-alkyl-7-methoxy-2-phenylbenzo[b]furans have been achieved. Subsequent transformation of the resulting formyl group into methyl, hydroxymethyl, 1-hydroxyethyl, and cyano groups are also described.

  DOI：

  10.1021/jo00052a046

文献信息

• Synthesis and analgesic activity of 1-[(1,2,3-triazol-1-yl)methyl]quinolizines based on the alkaloid lupinine
  作者：Zhangeldy S. Nurmaganbetov、Viktor A. Savelyev、Yurii V. Gatilov、Oralgazy A. Nurkenov、Roza B. Seidakhmetova、Zarina T. Shulgau、Gulim K. Mukusheva、Serik D. Fazylov、Elvira E. Shults

  DOI：10.1007/s10593-021-03000-7

  日期：2021.9

  ydro-1H-quinolizines with various substituents at the C-4 position of the triazole ring. The structures of lupinine methanesulfonate and 1-[(1,2,3-triazol-1-yl)methyl]octahydroquinolizines were confirmed by X-ray structural analysis. 1-[(1,2,3-Triazol-1-yl)methyl]octahydroquinolizines containing a hydroxymethyl or 2-hydroxypropan-2-yl substituent at the C-4 position of the triazole ring exhibit pronounced

  通过引入取代的 1,2,3-三唑对生物碱羽扇豆碱的喹嗪主链进行修饰。当 NaN 3作用于羽扇豆与甲磺酰氯的反应产物时，形成羽扇豆酰叠氮化物，在 CuSO 4水溶液和抗坏血酸钠存在下与末端炔烃反应形成相应的 (1 S ,9a R )-1- [(1,2,3-triazol-1-yl)-methyl]octahydro-1 H-在三唑环的 C-4 位具有各种取代基的喹啉。羽扇豆甲磺酸盐和 1-[(1,2,3-triazol-1-yl)methyl]octahydroquinolizines 的结构通过 X 射线结构分析得到证实。在三唑环的 C-4 位含有羟甲基或 2-羟基丙-2-基取代基的 1-[(1,2,3-三唑-1-基) 甲基]八氢喹啉具有显着的镇痛活性。
• 6-(4′-Aryl-1′,2′,3′-triazolyl)-spirostan-3,5-diols and 6-(4′-Aryl-1′,2′,3′-triazolyl)-7-hydroxyspirosta-1,4-dien-3-ones: Synthesis and analysis of their cytotoxicity
  作者：Maxim E. Mironov、Olga S. Oleshko、Mikhail A. Pokrovskii、Tatyana V. Rybalova、Vladislav K. Pechurov、Andrey G. Pokrovskii、Sergey V. Cheresis、Sergey V. Mishinov、Vyacheslav V. Stupak、Elvira E. Shults

  DOI：10.1016/j.steroids.2019.108460

  日期：2019.11

  potent anti-tumor agents from diosgenin, a series of C-6 derived 1,2,3-triazolyl derivatives were designed and synthesized by employing Cu(I) catalyzed Huisgen 1,3-dipolar cycloaddition reaction of novel azides - (22R,25R)-6β-azidospirostan-3β,5α-diol and 6β-azido-7α-hydroxyspirosta-1,4-dien-3-one with aryl(hetaryl)alkynes. All the derivatives were evaluated for cytotoxic activity by MTT assay against

  为了努力从薯os皂甙元开发有效的抗肿瘤药，利用新型叠氮化物的Cu（I）催化的Huisgen 1,3-偶极环加成反应设计并合成了一系列C-6衍生的1,2,3-三唑基衍生物-（22R，25R）-6β-叠氮螺螺-3-3,5α-二醇和6β-叠氮基-7α-羟基螺螺-1,4-dien-3-one与芳基（杂芳基）炔烃。通过MTT分析评估了所有衍生物对八种不同人类癌细胞系的细胞毒活性：T细胞白血病（CEM-13），人类单核细胞（U-937），乳腺（MDA-MB-231，BT-474），前列腺癌（DU-145）和胶质母细胞瘤（U-87MG，SNB-19，T98G）。这项研究的结果表明6-（4'-芳基-1'，2'，3'-三唑基）spirostan-3,5-二醇2、3、4、5和6具有潜在的细胞毒性潜力。相应的6-取代的7-羟基-1，4-spirostadien-3-ones对人类癌细胞的细胞毒性较小。化合物2、
• DBU‐Mediated Synthesis of Aryl Acetylenes or 1‐Bromoethynylarenes from Aldehydes
  作者：Yadagiri Thummala、Galla V. Karunakar、Venkata Ramana Doddi

  DOI：10.1002/adsc.201801334

  日期：2019.2

  sequential manner for the synthesis of arylacetylenes and 1,3‐enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1‐bromoalkynes intermediate

  两种众所周知的合成有机反应Ramirez烯化反应和Corey-fuchs反应以单锅顺序方式进行整合，以直接从市售醛开始合成芳基乙炔和1,3-烯炔。双环am1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）与添加剂NaOH不仅专门从醛中直接提供末端炔烃，而且还提高了反应速率。DBU的动态性质也促进了1-溴代炔烃中间产物的分离。从NaOH和H 2 O中选择添加剂可分别用作合成末端炔烃和1-溴代炔烃的开关。
• Facile Preparation of 2-Arylbenzo[b]furan Molecules and Their Anti-inflammatory Effects
  作者：Jung-Woon Hwang、Da-Hye Choi、Jae-Ho Jeon、Jin-Kyung Kim、Jong-Gab Jun

  DOI：10.5012/bkcs.2010.31.04.965

  日期：2010.4.20

  An efficient and practical preparation of 2-arylbenzo[b]furan molecules including natural egonol, XH-14, ailanthoidol, and unnatural derivatives is demonstrated using Sonogashira coupling, iodine induced cyclization and Wittig reaction. Anti-inflammatory effects of the prepared benzo[b]furans were examined in lipopolysaccharide (LPS)-stimulated RAW 264-7 macrophages. The results showed that ailanthoidol, XH-14 and three other unnatural derivatives (9-10, 13) inhibited significantly the production of inflammatory mediator nitric oxide without showing cytotoxicity.

  展示了一种高效且实用的合成2-芳基苯并[b]呋喃分子的制备方法，包括天然的艾戈诺尔、XH-14、白蜡醇和一些非天然衍生物，采用了SonogashiRA偶联、碘诱导环化和Wittig反应。所制备的苯并[b]呋喃的抗炎作用在脂多糖（LPS）刺激的RAW 264-7巨噬细胞中进行了检测。结果显示，白蜡醇、XH-14和其他三种非天然衍生物（9-10，13）显著抑制了炎性介质一氧化氮的生成，并且未表现出细胞毒性。
• Catalytic Asymmetric Synthesis of the <i>endo</i>-6-Aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one Natural Product from <i>Ligusticum chuanxing</i> via 1,3-Dipolar Cycloaddition of a Formyl-Derived Carbonyl Ylide Using Rh₂(<i>S</i>-TCPTTL)₄
  作者：Naoyuki Shimada、Taiki Hanari、Yasunobu Kurosaki、Koji Takeda、Masahiro Anada、Hisanori Nambu、Motoo Shiro、Shunichi Hashimoto

  DOI：10.1021/jo101175b

  日期：2010.9.3

  The reaction of a six-membered cyclic formyl-carbonyl ylide derived from α-diazo-β-ketoester with phenylacetylene derivatives under the catalysis of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh2(S-TCPTTL)4, provides cycloadducts containing an 8-oxabicyclo[3.2.1]octane ring system in up to 97% ee. This represents the first example of an enantioselective 1,3-dipolar cycloaddition

  六元环状甲酰基羰基叶立德的反应从α重氮基β酮酯与苯乙炔衍生物的二铑的催化下（II）四[ Ñ -tetrachlorophthaloyl-（小号） -叔-leucinate]的Rh 2（S- TCPTTL）4，提供包含高达97％ee的8-氧杂双环[3.2.1]辛烷环系统的环加合物。这代表了环状甲酰基-羰基内酯的对映选择性1，3-偶极环加成的第一个例子。使用该催化过程中，不对称合成内切-6-芳基-8-氧杂双环[3.2.1]辛-3-烯-2-酮的天然产物1从藁传兴园艺。已经实现。