2,3-二甲基丁-3-烯醛 | 80719-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 中文名称: 2,3-二甲基丁-3-烯醛
• 英文名称: 2,3-Dimethyl-3-butenal
• 英文别名: 2,3-dimethyl-but-3-enal；2,3-Dimethylbut-3-enal
• CAS: 80719-79-5
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: FULBADAVZOAOHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-二甲基丁-3-烯醛 在 三乙胺 、 zinc(II) chloride 作用下， 以 乙酸乙酯 为溶剂， 反应 27.0h， 生成 (2E,6E)-5,9,9-Triethoxy-2,3-dimethyl-nona-2,6-dienal
  参考文献：
  名称：

  Makin, S. M.; Kruglikova, R. I.; Popova, T. P., Journal of Organic Chemistry USSR (English Translation), 1982, p. 1001 - 1003

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二甲基-1,3-丁二烯 在 Nitrate 作用下， 以 gaseous matrix 为溶剂， 24.9 ℃ 、93.33 Pa 条件下， 生成 2,3-二甲基丁-3-烯醛
  参考文献：
  名称：

  Lancar, I. T.; Daele, V.; Le Bras, G., Journal de Chimie Physique et de Physico-Chimie Biologique, 1991, vol. 88, # 9, p. 1777 - 1792

  摘要：

  DOI：

文献信息

• Stereo- and regio-controlled aldol synthesis using relative 1,2-asymmetric induction
  作者：Fumie Sato、Yoshiyuki Takeda、Hiroshi Uchiyama、Yuichi Kobayashi

  DOI：10.1039/c39840001132

  日期：——

  addition of nucleophiles to α-methyl-β-methylene carbonyl compounds combined with the hydromagnesiation reactions of 2-alkyl-substituted 1,3-dienes affords a practical, efficient stereo- and regio-controlled aldol synthesis.

  亲核试剂向α-甲基-β-亚甲基羰基化合物的高度立体选择性加成与2-烷基取代的1,3-二烯的氢磁化反应相结合，提供了一种实用，有效的立体和区域控制的羟醛合成。
• The competitive and non-competitive hydroformylation of conjugated dienes starting with tetrarhodium dodecacarbonyl. An in-situ high-pressure infrared spectroscopic study
  作者：Guowei Liu、Marc Garland

  DOI：10.1016/s0022-328x(00)00369-7

  日期：2000.8

  known that the liquid-phase homogeneous unmodified rhodium catalysed hydroformylation of alkenes is poisoned by the presence of trace quantities of conjugated dienes. Nevertheless, some hydroformylation of conjugated dienes is possible with unmodified rhodium, and this reaction is in general slower than alkene hydroformylations at comparable reaction conditions. In the present contribution, we examined

  众所周知，液相的均相未改性铑催化的烯烃加氢甲酰化会因存在痕量的共轭二烯而中毒。然而，在未改性的铑条件下，共轭二烯的加氢甲酰化反应还是可能的，而且在可比的反应条件下，该反应通常比烯烃的加氢甲酰化反应慢。在本贡献中，我们检查（A）烯烃的痕量的存在下催化性能的共轭二烯的杂质和（B）的各种使用铑二烯烃的催化行为4（CO）12在ñ -己烷溶剂中在293度在1.0-4.0 MPa CO和0.5-2.0 MPa H 2下。分析方法是原位高压红外光谱法。观察到（I）在有毒烯烃的加氢甲酰化中，大多数铑在这种竞争情况下与痕量的共轭二烯发生反应，而不与烯烃发生反应；以及（II）各种二烯加氢甲酰化的金属羰基光谱非常相似。在共轭二烯的加氢甲酰化中观察到的一次吸光度最大值出现在大约2109、2091、2087、2064、2049、2037、2030、2020、2012、1999和1990 cm -1。给出铑的已知化学
• Copper-Catalyzed Rearrangement of Vinyl Oxiranes
  作者：Lindsay A. Batory、Christine E. McInnis、Jon T. Njardarson

  DOI：10.1021/ja067073o

  日期：2006.12.1

  A novel copper-catalyzed vinyl oxirane ring expansion protocol has been developed. A wide range of vinyl oxiranes can be rearranged to 2,5-dihydrofurans in excellent yields in the presence of electrophilic copper(II) acetylacetonate catalysts. Regioisomeric vinyl oxiranes can be converted to a single dihydrofuran product using these conditions. This method uses low catalyst loadings (0.5-5 mol %), has good tolerance of substitution patterns, and can be done in the absence of solvent.
• Prevost, Bulletin de la Societe Chimique de France, 1944, vol. <5>11, p. 223
  作者：Prevost

  DOI：——

  日期：——
• Visible light induced reactions of nitrogen dioxide with conjugated dienes in a low-temperature argon matrix
  作者：Nobuaki Tanaka、Yoshizumi Kajii、Kazuhiko Shibuya、Munetaka Nakata

  DOI：10.1021/j100129a020

  日期：1993.7

  Visible light induced oxygen atom transfer from NO2 to conjugated dienes has been investigated in a low-temperature Ar matrix, where the dienes are 1,3-butadiene (BD), 2-methyl-1,3-butadiene (isoprene), and 2,3-dimethyl-1,3-butadiene (DMB). In each diene/NO2/Ar system, the corresponding nitrite radical, oxirane, aldehyde, and NO were obtained as the photochemical reaction products. The reactions are initiated by the formation of undetectable short-lived oxirane biradical and NO due to visible light induced 0 atom transfer from NO2 to the conjugated dienes. (1) The recombination of oxirane biradicals and neighboring NO gives the nitrite radicals as the photochemical intermediate. (2) The ring closure of the biradicals leads to the formation of oxiranes. (3) The intramolecular H atom transfer of biradicals leads to the formation of aldehydes. The visible photolysis of the nitrite radicals gives rise to oxirane, aldehyde, and NO. The reaction rates are derived by measuring the absorbance changes of the products upon the 582-nm irradiation. The methyl substituent effect on the reactivity is discussed.