ethyl 5-(1-hydroxycyclohexyl)-5,6-heptadienoate | 141375-91-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 5-(1-hydroxycyclohexyl)-5,6-heptadienoate
• CAS: 141375-91-9
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: OIJOFCPXDWOQTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  γ-(Iodzinkio)buttersaeureethylester 在 chromium dichloride 、 溴 、 三苯基膦 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 3.5h， 生成 ethyl 5-(1-hydroxycyclohexyl)-5,6-heptadienoate
  参考文献：
  名称：

  Preparation of polyfunctional allenic alcohols by the regioselective addition of functionalized propargylic chromium(III) organometallics to carbonyl compounds

  摘要：

  The reaction of propargylic halides 1 (X = Cl, Br) with an aldehyde or ketone (0.67 equiv) in the presence of CrCl2 (2.0 equiv) and LiI (2 equiv, necessary if X = Cl) affords allenic alcohols 3 with excellent regioselectivities (3-6% of the regioisomeric acetylenic alcohol 4 is formed) and in good yields (68-90%). Interestingly, this method allows the generation of highly functionalized intermediate propargylic chromium organometallics contained an ester, cyano, or chloride functionality. The alpha-alkyl-substituted propargylic bromide 10 reacts with benzaldehyde yielding the acetylenic alcohol 11 as a diastereomeric mixture of only one regioisomer (90% yield).

  DOI：

  10.1021/jo00041a006

文献信息

• Preparation of polyfunctional allenic alcohols by the regioselective addition of functionalized propargylic chromium(III) organometallics to carbonyl compounds
  作者：Kevin Belyk、Michael J. Rozema、Paul Knochel

  DOI：10.1021/jo00041a006

  日期：1992.7

  The reaction of propargylic halides 1 (X = Cl, Br) with an aldehyde or ketone (0.67 equiv) in the presence of CrCl2 (2.0 equiv) and LiI (2 equiv, necessary if X = Cl) affords allenic alcohols 3 with excellent regioselectivities (3-6% of the regioisomeric acetylenic alcohol 4 is formed) and in good yields (68-90%). Interestingly, this method allows the generation of highly functionalized intermediate propargylic chromium organometallics contained an ester, cyano, or chloride functionality. The alpha-alkyl-substituted propargylic bromide 10 reacts with benzaldehyde yielding the acetylenic alcohol 11 as a diastereomeric mixture of only one regioisomer (90% yield).