1-(2,6,6-Trimethylcyclohex-2-en-1-yl)but-2-ynyl benzoate | 1277166-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2,6,6-Trimethylcyclohex-2-en-1-yl)but-2-ynyl benzoate
• CAS: 1277166-78-5
• 化学式: C₂₀H₂₄O₂
• 分子量: 296.409
• InChiKey: LDUQEIMATLSXFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  1-(2,6,6-Trimethylcyclohex-2-en-1-yl)but-2-ynyl benzoate 在 [{Au(IPr)}2(μ-OH)][BF4] 、 碘 作用下， 以 水 、 丁酮 、 二氯甲烷 为溶剂， 反应 14.0h， 以70%的产率得到alpha-ionone
  参考文献：
  名称：

  Gold-mediated synthesis of α-ionone

  摘要：

  A simple and convenient synthesis of a-ionone, an important component of flowers and fragrances, is reported. The key step in the formation of the a.,p-unsaturated ketone moiety involves an NHC-Au-1 catalyzed Meyer-Schuster-like rearrangement of readily prepared propargylic esters. The complex [{Au(IPr)}(2)(mu-OH)][BF4] proved to be the most efficient catalyst leading to a-ionone in 70% yield from a propargylic benzoate. This optimized procedure represents a valuable and attractive alternative to classical methods leading to alpha,beta-unsaturated ketones, such as the Wittig or aldol reactions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.010
• 作为产物：
  描述：

  1-(2,6,6-trimethyl-2-cyclohexenyl)-2-butyn-1-ol 、 苯甲酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以73%的产率得到1-(2,6,6-Trimethylcyclohex-2-en-1-yl)but-2-ynyl benzoate
  参考文献：
  名称：

  Gold-mediated synthesis of α-ionone

  摘要：

  A simple and convenient synthesis of a-ionone, an important component of flowers and fragrances, is reported. The key step in the formation of the a.,p-unsaturated ketone moiety involves an NHC-Au-1 catalyzed Meyer-Schuster-like rearrangement of readily prepared propargylic esters. The complex [{Au(IPr)}(2)(mu-OH)][BF4] proved to be the most efficient catalyst leading to a-ionone in 70% yield from a propargylic benzoate. This optimized procedure represents a valuable and attractive alternative to classical methods leading to alpha,beta-unsaturated ketones, such as the Wittig or aldol reactions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.010

文献信息

• Gold-mediated synthesis of α-ionone
  作者：Valentina Merlini、Sylvain Gaillard、Alessio Porta、Giuseppe Zanoni、Giovanni Vidari、Steven P. Nolan

  DOI：10.1016/j.tetlet.2011.01.010

  日期：2011.3

  A simple and convenient synthesis of a-ionone, an important component of flowers and fragrances, is reported. The key step in the formation of the a.,p-unsaturated ketone moiety involves an NHC-Au-1 catalyzed Meyer-Schuster-like rearrangement of readily prepared propargylic esters. The complex [Au(IPr)}(2)(mu-OH)][BF4] proved to be the most efficient catalyst leading to a-ionone in 70% yield from a propargylic benzoate. This optimized procedure represents a valuable and attractive alternative to classical methods leading to alpha,beta-unsaturated ketones, such as the Wittig or aldol reactions. (C) 2011 Elsevier Ltd. All rights reserved.