(E/Z)-2-methyl-3-undecene | 74630-48-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (E/Z)-2-methyl-3-undecene
• 英文别名: 2-methylundec-3-ene
• CAS: 74630-48-1；74630-51-6
• 化学式: C₁₂H₂₄
• 分子量: 168.323
• InChiKey: FBQHQLXAWUWXCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  4-heptyl-3-isopropyloxetan-2-one 反应 1.0h， 以75%的产率得到(E/Z)-2-methyl-3-undecene
  参考文献：
  名称：

  A practical and efficient method for the synthesis of .beta.-lactones

  摘要：

  This paper describes a convenient one-step preparation of beta-lactones based on the addition of thiol ester enolates to carbonyl compounds. Under the proper conditions the resulting aldolates undergo spontaneous cyclization to produce beta-lactones in good to excellent yield. The new beta-lactone synthesis provides access to 2-oxetanones with a variety of substituents and substitution patterns. In general, thiol ester enolates combine with carbonyl compounds to form the less sterically crowded beta-lactone diastereomers, and in some cases the reaction proceeds with excellent stereoselectivity. In conjunction with the stereospecific decarboxylation of beta-lactones, this chemistry also provides a very attractive approach to the synthesis of substituted alkenes.

  DOI：

  10.1021/jo00003a047

文献信息

• Hindered organoboron groups in organic chemistry. 25. The condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions to give alkenes.
  作者：Andrew Pelter、Keith Smith、Said M.A. Elgendy

  DOI：10.1016/s0040-4020(01)87983-7

  日期：1993.8

  In the presence of protic acids the condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions results in alkenes. In the presence of strong acids such as HCl or CF3SO3H, the products contain > 90% of E-alkenes in all cases tried. When acetic acid is used, then Z-alkenes may result predominantly, particularly in the cases of RsCHO and RtCHO. HX  HCI, CF3SO3H gives E - alkenes in

  在质子酸的存在下，脂族醛与二聚三苯甲基稳定的碳负离子的缩合会生成烯烃。在强酸（例如HCl或CF 3 SO 3 H）的存在下，在所有尝试的情况下，产品均含有> 90％的E-烯烃。当使用乙酸时，则可能主要产生Z-烯烃，特别是在R s CHO和R t CHO的情况下。在所有情况下，HXHCl，CF 3 SO 3 H均会生成E-烯烃。HXCH 3 CO 2 H，使得主要ž -烯烃当Rř秒，R叔。
• A practical and efficient method for the synthesis of .beta.-lactones
  作者：Rick L. Danheiser、James S. Nowick

  DOI：10.1021/jo00003a047

  日期：1991.2

  This paper describes a convenient one-step preparation of beta-lactones based on the addition of thiol ester enolates to carbonyl compounds. Under the proper conditions the resulting aldolates undergo spontaneous cyclization to produce beta-lactones in good to excellent yield. The new beta-lactone synthesis provides access to 2-oxetanones with a variety of substituents and substitution patterns. In general, thiol ester enolates combine with carbonyl compounds to form the less sterically crowded beta-lactone diastereomers, and in some cases the reaction proceeds with excellent stereoselectivity. In conjunction with the stereospecific decarboxylation of beta-lactones, this chemistry also provides a very attractive approach to the synthesis of substituted alkenes.