(E)-2-Methoxy-2-buten | 25125-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2-Methoxy-2-buten
• 英文别名: (E)-2-Methoxy-2-butene；(E)-2-methoxy-but-2-ene；2-Methoxy-cis-buten-(2)；2-Methoxybut-2-ene；(E)-2-methoxybut-2-ene
• CAS: 25125-84-2
• 化学式: C₅H₁₀O
• 分子量: 86.1338
• InChiKey: JWBPCSXRWORRAI-SNAWJCMRSA-N

物化性质

• 沸点：
  67.0±9.0 °C(Predicted)
• 密度：
  0.777±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2-Methoxy-2-buten 在 氧气 作用下， 生成 2-methoxy-1-methyl-allyl hydroperoxide
  参考文献：
  名称：

  On the relative reactivity of 1Σ vs. 1Δ02: Reactions of laser generated singlet oxygen with methoxy-olefins

  摘要：

  DOI：

  10.1016/s0040-4039(01)93959-0
• 作为产物：
  描述：

  (+/-)-erythro-2-Brom-3-methoxy-butan 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 (E)-2-Methoxy-2-buten
  参考文献：
  名称：

  Unsaturated carbenes from primary vinyl triflates. II. Spin multiplicity via the stereochemistry of addition to olefins

  摘要：

  DOI：

  10.1021/ja00839a030
• 作为试剂：
  描述：

  4-甲氧基吲哚-3-甲醛 在 sodium dihydrogenphosphate dihydrate 作用下， 以 (E)-2-Methoxy-2-buten 、 水 、 叔丁醇 为溶剂， 反应 48.0h， 以91%的产率得到4-甲氧基-1H-吲哚-3-甲酸
  参考文献：
  名称：

  Interaction of cruciferous phytoanticipins with plant fungal pathogens: Indole glucosinolates are not metabolized but the corresponding desulfo-derivatives and nitriles are

  摘要：

  Glucosinolates represent a large group of plant natural products long known for diverse and fascinating physiological functions and activities. Despite the relevance and huge interest on the roles of indole glucosinolates in plant defense, little is known about their direct interaction with microbial plant pathogens. Toward this end, the metabolism of indolyl glucosinolates, their corresponding desulfo-derivatives, and derived metabolites, by three fungal species pathogenic on crucifers was investigated. While glucobrassicin, 1-methoxyglucobrassicin, 4-methoxyglucobrassicin were not metabolized by the pathogenic fungi Alternaria brassicicola, Rhizoctonia solani and Sclerotinia sclerotiorum, the corresponding desulfo-derivatives were metabolized to indolyl-3-acetonitrile, caulilexin C (1-methoxyindolyl-3-acetonitrile) and arvelexin (4-methoxyindolyl-3-acetonitrile) by R. solani and S. sclerotiorum, but not by A. brassicicola. That is, desulfo-glucosinolates were metabolized by two non-host-selective pathogens, but not by a host-selective. Indolyl-3-acetonitrile, caulilexin C and arvelexin were metabolized to the corresponding indole-3-carboxylic acids. Indolyl-3-acetonitriles displayed higher inhibitory activity than indole desulfo-glucosinolates. Indolyl-3-methanol displayed antifungal activity and was metabolized by A. brassicicola and R. solani to the less antifungal compounds indole-3-carboxaldehyde and indole-3-carboxylic acid. Diindolyl-3-methane was strongly antifungal and stable in fungal cultures, but ascorbigen was not stable in solution and displayed low antifungal activity; neither compound appeared to be metabolized by any of the three fungal species. The cell-free extracts of mycelia of A. brassicicola displayed low myrosinase activity using glucobrassicin as substrate, but myrosinase activity was not detectable in mycelia of either R. solani or S. sclerotiorum. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2011.08.018

文献信息

• Generation and Reaction of Tungsten-Containing Carbonyl Ylides:  [3 + 2]-Cycloaddition Reaction with Electron-Rich Alkenes
  作者：Hiroyuki Kusama、Hideaki Funami、Masahide Shido、Yoshihiro Hara、Jun Takaya、Nobuharu Iwasawa

  DOI：10.1021/ja044194k

  日期：2005.3.1

  7c. Examination using (E)- or (Z)- vinyl ether revealed that the [3 + 2]-cycloaddition reaction proceeded in a concerted manner and that the facial selectivity of the reaction differed considerably depending on the presence or absence of triethylsilane. These results clarified the reversible nature of this [3 + 2]-cycloaddition reaction.

  新型含钨羰基叶立德 7，由邻炔基苯基羰基衍生物 1 与催化量的 W(CO)(5)(thf) 反应生成，与烯烃反应生成多环化合物 5 至 [3 + 2] -环加成反应，随后产生的不稳定的卡宾配合物中间体 8 的分子内 CH 插入。在三乙基硅烷的存在下，这些含钨的卡宾中间体 8 被三乙基硅烷顺利地分子间捕获，得到含硅的环加合物 17，同时 W(CO )(5) 种。通过该程序，可用于该反应的烯烃的范围得到澄清。通过直接观察邻乙炔基苯基酮 1c 和 W(CO)(5)(thf-d(8)) 的混合物，证实了含钨羰基叶立德 7c 的存在。通过 2D NMR 对中间体进行仔细分析，并观察到使用 (13)C 标记底物与钨 183 的直接偶联，证实了叶立德 7c 的结构。使用 (E)- 或 (Z)- 乙烯基醚的检查表明 [3 + 2]- 环加成反应以协同方式进行，并且反应的表面选择性因三乙基硅烷的存在或不存在而显着不同。这些结果阐明了这种
• Kinetics of the gas-phase thermal decompositions of 1-methoxy-1-methylcyclopropane and cis- and trans-1-methoxy-2-methylcyclopropane
  作者：Iftikhar A. Awan、Michael C. Flowers

  DOI：10.1039/f19858101415

  日期：——

  In the temperature range 665–737 K the thermal decomposition of 1-methoxy-1-methylcyclopropane follows first-order kinetics with a rate constant given by the equation, k/s–1= 1014.76±0.81 exp(–252±10 kJ mol–1/RT). The presence of the 1-methyl substituent destabilises the transition state for reaction. Secondary decomposition of the initially formed isomeric products precludes the determination of their

  在665–737 K的温度范围内，1-甲氧基-1-甲基环丙烷的热分解遵循一级动力学，其速率常数由方程式k / s –1 = 10 14.76±0.81 exp（–252±10 kJ摩尔–1 / R T）。1-甲基取代基的存在破坏了反应的过渡态。最初形成的异构体产物的二次分解使得无法确定其单独的形成速率。
• Heterogeneous chirality transfer on photooxygenation
  作者：Raymond Gerdil、Giacomo Barchietto、Charles W. Jefford

  DOI：10.1021/ja00337a077

  日期：1984.12

  Etude d'un nouveau cas d'induction dans lequel les cavites dissymetriques a l'interieur de cristaux de tri-o-thy-motide communique l'asymetrie a la reaction d'une substance euclathratee les methoxy-2 butenes-2 cis et trans

  Etude d'un nouveau cas d'induction dans lequel les cavites dissymetriques a l'interieur de cristaux de tri-o-thy-motide 公报 l'asymetrie a la反应 d'une 物质 euclathratee les methoxy-2 butenes-2 cis et trans
• Kirmse, Wolfgang; Rode, Jutta; Rode, Klaus, Chemische Berichte, 1986, vol. 119, # 12, p. 3672 - 3693
  作者：Kirmse, Wolfgang、Rode, Jutta、Rode, Klaus

  DOI：——

  日期：——
• Asymmetric hydroboration of [ E ]- and [ Z ]-2-methoxy-2-butenes. Synthesis of (−)-[2 R ,3 R ]-butane-2,3-diol in >97% ee
  作者：Dhanabalan Murali、Bakthan Singaram、Herbert C. Brown

  DOI：10.1016/s0957-4166(00)00485-7

  日期：2000.12

  Asymmetric hydroboration of [E]- and [Z]-2-methoxy-2-butene, using (-)-diisopinocampheylborane at -25 degreesC in THF solvent, followed by oxidation using H2O2/NaOH, gave (-)-[2R,3R]- and (+)-[2R,3S]-3-methoxy-2-butanols in >97 and 90% ee, respectively. (-)-[2R,3R]-3-Methoxy-2-butanol was converted to (-)-[2R,3R]-butane-2,3-diol (>97% ee, in an overall yield of 65%). (C) 2001 Elsevier Science Ltd. All rights reserved.