4-methoxy-3-(3-methylbut-3-en-1-ynyl)benzaldehyde | 121007-18-9

• 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)benzaldehyde
• 英文别名: Methyleutypine
• CAS: 121007-18-9
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: SXRUMPFFTDBUEF-UHFFFAOYSA-N

物化性质

• 熔点：
  45.5-48 °C
• 沸点：
  345.1±42.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methoxy-3-(3-methylbut-3-en-1-ynyl)benzaldehyde 在 N,N-二甲基丙烯基脲 、 lithium chloride 作用下， 反应 2.0h， 以50%的产率得到5-formyl-2-isopropenylbenzofuran
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基-3-碘苯甲醛 在 ammonium hydroxide 、 copper(l) iodide 、 盐酸羟胺 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 4-methoxy-3-(3-methylbut-3-en-1-ynyl)benzaldehyde
  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

• Palladium-catalyzed arylation of polar organometallics mediated by 9-methoxy-9-borabicyclo[3.3.1]nonane: Suzuki reactions of extended scope
  作者：Alois Fürstner、Günter Seidel

  DOI：10.1016/0040-4020(95)00677-z

  日期：1995.10

  organometallic reagent RM, and not as usually from a borane and a base. This approach allows cross couplings of aryl halides with e.g. alkynyl-, methyl-, or TMSCH2-groups, which were beyond the scope of the conventional Suzuki reaction. The method is highly chemoselective and turned out to be compatible with aldehyde-, amide-, ketone-, ester- and cyano functions as well as with basic nitrogen atoms

  提出了进行铃木反应的另一种方法。由9-甲氧基-9-硼双环[3.3.1]壬烷（9-OMe-9-BBN）和极性有机金属试剂RM制备这些钯催化的CC键形成中实际的亲核试剂所必需的硼酸盐，而不是通常从硼烷和碱中提取。该方法允许芳基卤化物与例如炔基，甲基或TMSCH 2-基交叉偶联，这超出了常规的Suzuki反应的范围。该方法具有高度的化学选择性，并且与醛，酰胺，酮，酯和氰基官能团以及底物中的碱性氮原子兼容。它被用于合成炔属天然产物朱尼普尔（9a）和奥替平甲基醚（10）。自从11 B NMR研究表明，9-OMe-9-BBN仅用作传递RM试剂的穿梭物，但在反应过程中保持不变，因此有可能将第一个亚化学计量的Suzuki型反应装置硼。该“催化”方案用于制备化合物8，该化合物因其化学发光特性而非常有价值。
• 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.
• 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。
• 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：——