3-methyl-3,4-pentadien-2-ol | 37077-92-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-3,4-pentadien-2-ol
• 英文别名: 3-methylpenta-3,4-dien-2-ol；3-methyl-penta-3,4-dien-2-ol；3-Methyl-1,2-pentadien-4-ol
• CAS: 37077-92-2
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: DFZWAUZLJJZQLX-UHFFFAOYSA-N

物化性质

• 沸点：
  139.1±8.0 °C(Predicted)
• 密度：
  0.824±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-3,4-pentadien-2-ol 在 四(三苯基膦)钯 4-二甲氨基吡啶 、 四丁基溴化铵 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 乙醚 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 50.0h， 生成 trans-1,1-bis(methoxycarbonyl)-2-methyl-2-(1'-phenylethenyl)-3-methylcyclopropane
  参考文献：
  名称：

  Highly Regio- and Stereoselective Synthesis of Polysubstituted Cyclopropane Compounds via the Pd(0)-Catalyzed Coupling−Cyclization Reaction of 2-(2‘,3‘-Allenyl)malonates with Organic Halides

  摘要：

  A new method for highly regio- and stereoselective synthesis of polysubstituted cyclopropane compounds via the Pd(0)-catalyzed coupling-cyclization reaction of 2-(2',3'-allenyl)malonates with organic halides is described. In these reactions, the starting materials are easily available and the operation is convenient. The ratios of trans-isomer/ cis-vinylic cyclopropanes are up to 98:2.

  DOI：

  10.1021/jo049323u
• 作为产物：
  描述：

  1-(2,2-Dibrom-1-methyl-cyclopropyl)aethanol 在 甲基锂 作用下， 生成 3-methyl-3,4-pentadien-2-ol
  参考文献：
  名称：

  Selective reactions of alkylated 1-acyl-2,2-dibromocyclopropanes

  摘要：

  DOI：

  10.1016/s0040-4039(00)91081-5

文献信息

• Maurin,R.; Bertrand,M., Bulletin de la Societe Chimique de France, 1972, p. 2349 - 2355
  作者：Maurin,R.、Bertrand,M.

  DOI：——

  日期：——
• Efficient Synthesis of 4-(2‘-Alkenyl)-2,5-dihydrofurans and 5,6-Dihydro-2<i>H</i>-pyrans via the Pd-Catalyzed Cyclizative Coupling Reaction of 2,3- or 3,4-Allenols with Allylic Halides
  作者：Shengming Ma、Wenzhong Gao

  DOI：10.1021/jo0163997

  日期：2002.8.1

  In the absence of a base, palladium(II) catalysts, such as PdCl2, PdCl2(CH3CN)(2), Pd(OAc)(2), and [(pi-C3H5)PdCl](2), can catalyze the cyclizative coupling reaction of 2,3- or 3,4-allenols with allylic halides in DMA at room temperature to provide 2,5-dihydrofurans and 5,6-dihydro-2H-pyrans, respectively, in moderate to good yields. Under similar reaction conditions, nonsubstituted 2,3-allenol 1s affords bimolecular cyclizative coupling product 5s as the major product. The scope of the reaction and its mechanism have been studied briefly. On the basis of the experimental results, the transformation was believed to proceed via a divalent palladium-catalyzed pathway.
• Efficient synthesis of 4-(2′-alkenyl)-2,5-dihydrofurans via PdCl2-catalyzed coupling–cyclization reaction of 2,3-allenols with allylic halides
  作者：Shengming Ma、Wenzhong Gao

  DOI：10.1016/s0040-4039(00)01585-9

  日期：2000.11

  4-(2'-Alkenyl)-2, 5-dihydrofurans can be efficiently synthesized via the PdCl2-catalyzed coupling-cyclization of allylic halides with 2,3-allenols in DMA at rt in moderate to good yields. The regioselectivity is different from that of the Pd(0)-catalyzed coupling-cyclization of organic halides with 2,3-allenols. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Nilsen, Nils O.; Skattebol, Lars; Sydnes, Leiv K., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 9, p. 587 - 592
  作者：Nilsen, Nils O.、Skattebol, Lars、Sydnes, Leiv K.

  DOI：——

  日期：——
• Maurin,R.; Bertrand,M., Bulletin de la Societe Chimique de France, 1970, p. 2261 - 2270
  作者：Maurin,R.、Bertrand,M.

  DOI：——

  日期：——