(S)-(E)-4-Acetoxy-1-cyclohexyl-2-nonen-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(E)-4-Acetoxy-1-cyclohexyl-2-nonen-1-one
• 英文别名: [(E,4S)-1-cyclohexyl-1-oxonon-2-en-4-yl] acetate
• 化学式: C₁₇H₂₈O₃
• 分子量: 280.408
• InChiKey: UEWOBSRILLSYLF-DBTPVHCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  、 环己甲酰氯 以83%的产率得到
  参考文献：
  名称：

  Ostwald Roswitha, Chavant Pierre-Yves, Stadtmueller Heinz, Knochel Paul, J. Org. Chem., 59 (1994) N 15, S 4143-4153

  摘要：

  DOI：

文献信息

• Brieden, Walter; Ostwald, Roswitha; Knochel, Paul, Angewandte Chemie, 1993, vol. 105, # 4, p. 629 - 631
  作者：Brieden, Walter、Ostwald, Roswitha、Knochel, Paul

  DOI：——

  日期：——
• Catalytic Asymmetric Addition of Polyfunctional Dialkylzincs to .beta.-Stannylated and .beta.-Silylated Unsaturated Aldehydes
  作者：Roswitha Ostwald、Pierre-Yves Chavant、Heinz Stadtmueller、Paul Knochel

  DOI：10.1021/jo00094a027

  日期：1994.7

  The addition of functionalized dialkylzincs to readily available beta-stannylated or beta-silylated unsaturated aldehydes in the presence of a catalytic amount of (1R,2R)-1,2-bis(trifluorosulfonamido)cyclohexane (8 mol%) provides chiral allylic alcohols in good yields (60-90%) and excellent enantioselectivity (usually in the range of 85-95% ee). The synthetic utility of these allylic alcohols as chiral building blacks is demonstrated. The gamma-stannylated allylic alcohols were submitted to a Stille coupling leading to polyfunctional allylic alcohols and gamma-alkoxy enones. A treatment with CuCN in N-methylpyrrolidone at 130 degrees C provided chiral unsaturated gamma-hydroxy nitriles. Finally, the desilylation of the gamma-silylated alcohols gave chiral allylic alcohols having a terminal double bond. The catalytic asymmetric addition was found to show an important inverse temperature dependance. A mechanism for this addition is proposed.
• Ostwald Roswitha, Chavant Pierre-Yves, Stadtmueller Heinz, Knochel Paul, J. Org. Chem., 59 (1994) N 15, S 4143-4153
  作者：Ostwald Roswitha, Chavant Pierre-Yves, Stadtmueller Heinz, Knochel Paul

  DOI：——

  日期：——