oct-1-en-2-yl cinnamate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: oct-1-en-2-yl cinnamate
• 英文别名: oct-1-en-2-yl (E)-3-phenylprop-2-enoate
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: SHJBOANYFBUSPV-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-辛炔 、 肉桂酸 在 六氟磷酸银 、 三苯基膦氯金 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以78%的产率得到oct-1-en-2-yl cinnamate
  参考文献：
  名称：

  Gold(I)-Catalyzed Addition of Carboxylic Acids to Alkynes

  摘要：

  Au(I)-catalyzed hydroacyloxylation of alkynes with carboxylic acids is described PPh3AuCl/AgPF6 catalyst affords the Markonikov addition products, whereas PPh3AuCl/AgOTf catalyst gives the more stable isomerized products via the Markonikov products

  DOI：

  10.1021/jo101543q

文献信息

• Synthesis of enol and vinyl esters catalyzed by an iridium complex
  作者：Hideto Nakagawa、Yoshio Okimoto、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1016/s0040-4039(02)02451-6

  日期：2003.1

  Enol and vinyl esters were successfully synthesized by the use of an iridium complex as a catalyst. The reaction of carboxylic acids with terminal alkynes in the presence of catalytic amounts of [Ir(cod)Cl]2 and Na2CO3 gave the corresponding 1-alkenyl esters. The addition of carboxylic acids to alkynes principally took place in the Markovnikov fashion. In addition, by the use of an Ir complex combined

  通过使用铱配合物作为催化剂成功地合成了烯醇和乙烯基酯。在催化量的[Ir（cod）Cl] 2和Na 2 CO 3的存在下，羧酸与末端炔烃的反应得到相应的1-烯基酯。羧酸向炔烃中的添加主要以马尔可夫尼可夫的方式进行。另外，通过使用与NaOAc结合的Ir配合物，通过羧酸和乙酸乙烯酯之间的转乙烯基，制备了各种乙烯基酯。
• Enantioselective Redox-Neutral Rh-Catalyzed Coupling of Terminal Alkynes with Carboxylic Acids Toward Branched Allylic Esters
  作者：Philipp Koschker、Matthias Kähny、Bernhard Breit

  DOI：10.1021/jacs.5b01131

  日期：2015.3.4

  We report on the first enantioselective variant of the atom-economic and redox-neutral coupling of carboxylic acids with terminal alkynes under rhodium catalysis utilizing the chiral, bidentate (R,R)-Cp-DIOP ligand. This represents the first example of this convenient asymmetric access to valuable branched allylic esters. The utility of this methodology is demonstrated by both a reaction performed on large scale and a short three-step synthesis of two naturally occurring gamma-butyrolactones. A stereochemical model explaining the observed absolute configuration of the products based on DFT calculations is given.
• Gold(I)-Catalyzed Addition of Carboxylic Acids to Alkynes
  作者：Bathoju Chandra Chary、Sunggak Kim

  DOI：10.1021/jo101543q

  日期：2010.11.19

  Au(I)-catalyzed hydroacyloxylation of alkynes with carboxylic acids is described PPh3AuCl/AgPF6 catalyst affords the Markonikov addition products, whereas PPh3AuCl/AgOTf catalyst gives the more stable isomerized products via the Markonikov products