4-methoxy-3-(3-methylbut-3-en-1-ynyl)benzyl alcohol | 121007-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methoxy-3-(3-methylbut-3-en-1-ynyl)benzyl alcohol
• 英文别名: Methyleutypinol；[4-methoxy-3-(3-methylbut-3-en-1-ynyl)phenyl]methanol
• CAS: 121007-15-6
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: DHEWMSAMJLJBQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲基-N-(三甲基硅烷基)三氟乙酰胺 、 4-methoxy-3-(3-methylbut-3-en-1-ynyl)benzyl alcohol 在 吡啶 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  Dying-Arm Disease in Grapevines:  Diagnosis of Infection with Eutypa lata by Metabolite Analysis

  摘要：

  Dying-arm disease in grapevines, produced by infection with the ascomycete Eutypa lata, is responsible for major production losses in vineyards. Dieback of the shoots and cordon is believed to be due to acetylenic phenol metabolites produced by the fungus. To identify specific metabolites that could potentially be used for diagnosis of infection, eight E lata isolates were grown in vitro on hot water extracts from grape varieties with various degrees of tolerance to the foliar symptoms of E lata dieback. HPLC analysis showed that eutypinol was consistently produced in large amounts, together with smaller amounts of methyleutypinol and eulatachromene; eutypine, the putative toxin, was produced solely on Sauvignon Blanc extract and then in only barely detectable amounts. When E lata isolates from Cabernet Sauvignon and Merlot were grown on identical media, the amounts of metabolites produced differed significantly between isolates but the pattern of metabolites was quite similar, with eutypinol again predominating. The consistent production of eutypinol indicated that this was the most suitable metabolite for which to analyze in order to diagnose the presence of E lata. Extraction and analysis of grapevine tissues exhibiting symptoms of dieback failed to show the presence of any metabolites. However, when infected cordon sections were placed in water and cultured for 5 days, eutypinol was readily detected in the aqueous solution; metabolites were not produced from uninfected tissue. This provides a method for detection of infected tissue and indicates that the toxic metabolites react at the point of production, disrupting the vascular structure and inhibiting transport of nutrients, rather than being translocated to tissues that exhibit symptoms.

  DOI：

  10.1021/jf0510236
• 作为产物：
  描述：

  2-甲基-1-丁烯-3-炔 在 ammonium hydroxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 copper(l) iodide 、 盐酸羟胺 作用下， 反应 5.0h， 生成 4-methoxy-3-(3-methylbut-3-en-1-ynyl)benzyl alcohol
  参考文献：
  名称：

  从Eutypa lata（Pers; F.）TUL合成天然乙炔化合物

  摘要：

  一系列新炔属化合物的合成1 - 7，最近从真菌中分离Eutypa LATA，进行说明。关键步骤是受保护的芳基卤化物与炔属链之间的偶联反应，即乙炔化亚铜（流程1）。还成功地使用了双（三苯基膦）二氯化钯（[Pd（PPh 3）2 Cl 2 ]）作为催化剂，效率更高。

  DOI：

  10.1002/hlca.19930760126

文献信息

• Hiroya, Kou; Hashimura, Kazuya; Ogasawara, Kunio, Heterocycles, 1994, vol. 38, # 11, p. 2463 - 2472
  作者：Hiroya, Kou、Hashimura, Kazuya、Ogasawara, Kunio

  DOI：——

  日期：——
• TSOUPRAS, G.;DE, ANGELIS P.;ZESIGER, T.;RENAUD, J. M.;TABACCHI, R., CHEM. AND BIOL. NATURALLY OCCURING ACETYLENES AND RELAT. COMPOUNDS (NOARC+
  作者：TSOUPRAS, G.、DE, ANGELIS P.、ZESIGER, T.、RENAUD, J. M.、TABACCHI, R.

  DOI：——

  日期：——
• The Synthesis of Natural Acetylenic Compounds fromEutypa lata (Pers; F.) TUL
  作者：Eric Defranq、Thierry Zesiger、Rattaele Tabacchi

  DOI：10.1002/hlca.19930760126

  日期：1993.2.10

  The synthesis of a series of novel acetylenic compounds 1–7, isolated recently from the fungus Eutypa lata, is described. The crucial step is the coupling reaction between a protected aryl halogenide and the acetylenic chain as a cuprous acetylide (Scheme 1). A more efficient method using bis(triphenylphosphine)palladium dichloride ([Pd(PPh3)2Cl2]) as catalyst was also carried out with success.

  一系列新炔属化合物的合成1 - 7，最近从真菌中分离Eutypa LATA，进行说明。关键步骤是受保护的芳基卤化物与炔属链之间的偶联反应，即乙炔化亚铜（流程1）。还成功地使用了双（三苯基膦）二氯化钯（[Pd（PPh 3）2 Cl 2 ]）作为催化剂，效率更高。
• Dying-Arm Disease in Grapevines:  Diagnosis of Infection with <i>Eutypa lata</i> by Metabolite Analysis
  作者：Noreen Mahoney、Russell J. Molyneux、Leverett R. Smith、Thomas K. Schoch、Philippe E. Rolshausen、W. Douglas Gubler

  DOI：10.1021/jf0510236

  日期：2005.10.1

  Dying-arm disease in grapevines, produced by infection with the ascomycete Eutypa lata, is responsible for major production losses in vineyards. Dieback of the shoots and cordon is believed to be due to acetylenic phenol metabolites produced by the fungus. To identify specific metabolites that could potentially be used for diagnosis of infection, eight E lata isolates were grown in vitro on hot water extracts from grape varieties with various degrees of tolerance to the foliar symptoms of E lata dieback. HPLC analysis showed that eutypinol was consistently produced in large amounts, together with smaller amounts of methyleutypinol and eulatachromene; eutypine, the putative toxin, was produced solely on Sauvignon Blanc extract and then in only barely detectable amounts. When E lata isolates from Cabernet Sauvignon and Merlot were grown on identical media, the amounts of metabolites produced differed significantly between isolates but the pattern of metabolites was quite similar, with eutypinol again predominating. The consistent production of eutypinol indicated that this was the most suitable metabolite for which to analyze in order to diagnose the presence of E lata. Extraction and analysis of grapevine tissues exhibiting symptoms of dieback failed to show the presence of any metabolites. However, when infected cordon sections were placed in water and cultured for 5 days, eutypinol was readily detected in the aqueous solution; metabolites were not produced from uninfected tissue. This provides a method for detection of infected tissue and indicates that the toxic metabolites react at the point of production, disrupting the vascular structure and inhibiting transport of nutrients, rather than being translocated to tissues that exhibit symptoms.