2-ethyl-hept-5-ynal | 874771-09-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-ethyl-hept-5-ynal
• 英文别名: (2R)-2-ethylhept-5-ynal
• CAS: 874771-09-2
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: FFUVBCWQMHGINN-SECBINFHSA-N

物化性质

• 沸点：
  202.0±23.0 °C(Predicted)
• 密度：
  0.874±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  10.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-ethyl-hept-5-ynal 在 bis(1,5-cyclooctadiene)nickel (0) 、 三乙基硼 、 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 15.75h， 生成 8-ethyl-2,4-dimethyl-deca-4,9-dien-3-ol
  参考文献：
  名称：

  Directing effects of tethered alkenes in nickel-catalyzed coupling reactions of 1,6-enynes and aldehydes

  摘要：

  Nickel-catalyzed reductive coupling reactions of aldehydes and 1,6-enynes proceed in excellent regioselectivity in the absence of a phosphine, and the use of a monodentate phosphine additive leads to the formation of the opposite regioisomer with equally high selectivity. Both products are the result of the same fundamental mechanism, with the inversion of regioselectivity being the result of stereospecific ligand substitution at the metal center. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.122
• 作为产物：
  描述：

  (2R)-2-乙基庚-5-炔-1-醇 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到2-ethyl-hept-5-ynal
  参考文献：
  名称：

  Directing effects of tethered alkenes in nickel-catalyzed coupling reactions of 1,6-enynes and aldehydes

  摘要：

  Nickel-catalyzed reductive coupling reactions of aldehydes and 1,6-enynes proceed in excellent regioselectivity in the absence of a phosphine, and the use of a monodentate phosphine additive leads to the formation of the opposite regioisomer with equally high selectivity. Both products are the result of the same fundamental mechanism, with the inversion of regioselectivity being the result of stereospecific ligand substitution at the metal center. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.122

文献信息

• Mechanistic Implications of Nickel-Catalyzed Reductive Coupling of Aldehydes and Chiral 1,6-Enynes
  作者：Ryan M. Moslin、Timothy F. Jamison

  DOI：10.1021/ol052719n

  日期：2006.2.1

  [GRAPHICS]A study of nickel-catalyzed reductive coupling reactions of aldehydes and chiral 1,6-enynes has provided evidence for three distinct mechanistic pathways that govern regioselectivity in this transformation. In the absence of a phosphine additive, high regioselectivity and high diastereoselectivity are obtained as a direct result of coordination of both the alkyne and the olefin to the metal center during the C-C bond-forming step.