2-methylbuta-2,3-dien-1-yl acetate | 172791-35-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-methylbuta-2,3-dien-1-yl acetate
• 英文别名: 4-acetoxy-3-methyl-buta-1,2-diene；1-acetoxy-2-methyl-2,3-butadiene；4-Acetoxy-3-methyl-butadien-(1,2)
• CAS: 172791-35-4
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: LSGLQEGUKKGUSU-UHFFFAOYSA-N

物化性质

• 沸点：
  162.1±10.0 °C(Predicted)
• 密度：
  0.893±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  2-methylbuta-2,3-dien-1-yl acetate 在 NaOH 、 NaBH₄ 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3-methyl-1,3-butadien-2-yl)[4-(dimethylamino)pyridine]bis(dimethylglyoximato)cobalt(III)
  参考文献：
  名称：

  Stokes, Heather L.; Matthew Richardson; Wright, Marcus W., Organometallics, 1995, vol. 14, # 12, p. 5520 - 5532

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-1-丁烯-3-炔 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 生成 2-methylbuta-2,3-dien-1-yl acetate
  参考文献：
  名称：

  Traynard,J.-C., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1960, vol. 250, p. 1504 - 1506

  摘要：

  DOI：

文献信息

• Preparation and Subsequent Reaction Chemistry of Cyclopentadienyl Molybdenum Dicarbonyl η³-2-Alkylidene Cyclobutanonyl Complexes
  作者：N. Ariane Vinson、Cynthia S. Day、Mark E. Welker

  DOI：10.1021/om000546u

  日期：2000.10.1

  cyclobutanonyl and/or η3-butadienyl complexes. The 2-alkylidene cyclobutanone can be synthetically modified, while still complexed to molybdenum, by nucleophilic addition to the carbonyl or via enolate chemistry. The cyclobutanone can then be removed from the metal via oxidative demetalation. Several of the new complexes reported here have been characterized by X-ray crystallography.

  与各种亲电子丙二烯的阴离子Cyclopentadienylmolybdenumtricarbonyl反应产生η 3 -2-亚烷基cyclobutanonyl和/或η 3个-butadienyl络合物。通过将亲核加成到羰基上或通过烯醇盐化学反应，可以将2-亚烷基环丁酮合成修饰，同时仍与钼络合。然后可以通过氧化脱金属从金属中除去环丁酮。X射线晶体学表征了这里报道的几种新的复合物。
• Photoredox cobalt-catalyzed stereodivergent synthesis of 1,4-dienes
  作者：Xing-Yu Ren、Jia-Jun Liu、Shi-Qi Zhang、Yan-Lin Li、Kun Cui、Jing Li、Zheng-Yang Gu、Ji-Bao Xia

  DOI：10.1016/s1872-2067(24)60031-8

  日期：2024.6

  report a highly efficient method for the straightforward synthesis of 1,4-dienes regio- and stereoselective reductive coupling of alkynes and allenes, catalyzed by visible-light photoredox cobalt. In contrast to the conventional -alkene products, both (,) and (,)-1,4-dienes were synthesized with good regio- and stereoselectivities under mild conditions. In this photoredox reaction, Hünig’s base and

  1,4-二烯是广泛用于天然产物和药物化合物的重要支架。在此，我们报告了一种在可见光光氧化还原钴催化下直接合成炔烃和丙二烯的1,4-二烯区域选择性和立体选择性还原偶联的高效方法。与传统的α-烯烃产物相比，(,)和(,)-1,4-二烯在温和条件下合成具有良好的区域选择性和立体选择性。在该光氧化还原反应中，使用 Hünig 碱和水作为氢源，而不是常用的 Hantzsch 酯。机理和密度泛函理论研究表明，该反应经历了钴环戊烯中间体的质子分解和(,)-1,4-二烯的光催化→异构化为(,)-1,4-二烯的能量转移过程。
• Chromium(III) catalyzed synthesis of allenes from propargyl derivatives via a carbometalation–elimination sequence
  作者：Gary A. Molander、Erin M. Sommers

  DOI：10.1016/j.tetlet.2005.01.143

  日期：2005.3

  The syn-carbometalation/syn-elimination of propargyl substrates to form allenes has been achieved using cationic chromium(III) catalysts activated by alkylaluminums. The mechanism and scope of this transformation are presented. (c) 2005 Elsevier Ltd. All rights reserved.
• Iridium-Catalyzed Hydrocarboxylation of 1,1-Dimethylallene:  Byproduct-Free Reverse Prenylation of Carboxylic Acids
  作者：In Su Kim、Michael J. Krische

  DOI：10.1021/ol702914p

  日期：2008.2.1

  Exposure of carboxylic acids 1a-12a to commercially available 1,1-dimethylallene in the presence of substoichiometric quantities of an iridium catalyst prepared in situ from [ir(cod)Cl](2) and BIPHEP provides the corresponding 1,1-dimethylallyl (reverse prenyl) esters 1b-12b in 74-92% isolated yield. This protocol represents the first branch-regioselective allene hydrocarboxylation. Stoichiometric byproducts are not generated in this process and protecting groups are not required for alcohols, phenols, and indolic amines.
• Preparation and Characterization of Molybdenum Tris(pyrazolyl)borate Dicarbonyl η³-Dienyl Complexes
  作者：Dean R. Lantero、Anne G. Glenn、Cynthia S. Day、Mark E. Welker

  DOI：10.1021/om030114u

  日期：2003.5.1

  Treatment of allenic electrophiles with Mo(CO)(3)(py)(3) followed by potassium hydrotris(l-pyrazolyl)borate (KTp) or treatment of an enyne with TpMo(CO)(3)H followed by decarbonylation cleanly produced stable, new eta(3)-dienyl complexes.