1-phenethyl-but-3-enyl benzoate

• 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-phenethyl-but-3-enyl benzoate
• 英文别名: 1-phenethylbut-3-enyl benzoate；1-phenylhex-5-en-3-yl benzoate
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: LBQSMMCGJGVXIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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-phenethyl-but-3-enyl benzoate 在 草酰氯 、 二甲基亚砜 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 6-oxo-1-phenylhexan-3-yl benzoate
  参考文献：
  名称：

  通过碘催化脂族醛的非对映选择性氧化α-胺化：合成顺-γ羟基α氨基缩醛†

  摘要：

  醛可以与仲胺反应，得到α -氨基缩醛经由通过碘催化脂族醛的α-胺化。发现在醛的γ-位上存在不对称羟基化中心可诱导立体选择性氨基。该方法代表了γ-羟基醛的立体选择性α-胺化反应，用于在非常温和的条件下以良好的收率和合理的非对映选择性合成合成-γ-羟基-α-氨基乙缩醛。

  DOI：

  10.1039/c3ob42043d
• 作为产物：
  描述：

  苯丙醛 在 sodium hydride 、 氯化铵 、 锌 作用下， 以 四氢呋喃 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 为溶剂， 反应 1.17h， 生成 1-phenethyl-but-3-enyl benzoate
  参考文献：
  名称：

  通过碘催化脂族醛的非对映选择性氧化α-胺化：合成顺-γ羟基α氨基缩醛†

  摘要：

  醛可以与仲胺反应，得到α -氨基缩醛经由通过碘催化脂族醛的α-胺化。发现在醛的γ-位上存在不对称羟基化中心可诱导立体选择性氨基。该方法代表了γ-羟基醛的立体选择性α-胺化反应，用于在非常温和的条件下以良好的收率和合理的非对映选择性合成合成-γ-羟基-α-氨基乙缩醛。

  DOI：

  10.1039/c3ob42043d

文献信息

• Nucleophilic Acyl Substitutions of Anhydrides with Protic Nucleophiles Catalyzed by Amphoteric, Oxomolybdenum Species
  作者：Chien-Tien Chen、Jen-Huang Kuo、Vijay D. Pawar、Yogesh S. Munot、Shieu-Shien Weng、Cheng-Hsiu Ku、Cheng-Yuan Liu

  DOI：10.1021/jo048363v

  日期：2005.2.1

  [GRAPHICS]Among six different group VIb oxometallic species examined, dioxomolybdenum dichloride and oxomolybdenum tetrachloride were the most efficient catalysts to facilitate nucleophilic acyl substitution (NAS) of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. In contrast to the well-recognized redox chemical behaviors associated with oxomolybdenum(VI) species, the catalytic NAS was unprecedented and tolerates virtually all kinds of functional groups. By using benzoic anhydride as a mediator for in situ generation of an incipient mixed anhydride -MoO2Cl2 adduct with a given functional alkanoic acid, one can achieve oleate, dipeptide, diphenylmethyl, N-Fmoc-alpha-amino, pyruvic, and tert-butylthio ester, N-tert-butylamide, and trityl methacrylate syntheses with appropriate protic nucleophiles. The amphoteric character of the Mo=O unit in oxomolybdenum chlorides was found to be responsible for the catalytic NAS profile as supported by a control NAS reaction of using an authentic adduct-MoOCl2(O-2-CBut)(2) between pivalic anhydride and MoO2Cl2 as the catalyst.
• Transesterification catalyzed by iron(III) β-diketonate species
  作者：Shiue-Shien Weng、Chih-Shueh Ke、Fong-Kuang Chen、You-Fu Lyu、Guan-Ying Lin

  DOI：10.1016/j.tet.2011.01.009

  日期：2011.3

  A practical and clean protocol for transesterification catalyzed by a 5 mol % cheap, non-toxic and moisture stable Fe(acac)(3) or other iron(III) beta-diketonate species in solvent, such as heptane under azeotropic condition is developed. A remarkable rate enhancement was observed upon the addition of 5 mol % of an inorganic base, such as Na2CO3, which suggests that faster formation of a dimeric mu-alkoxy-bridged iron (III) species under alkaline conditions facilitates catalytic turnover. This system provides smooth transesterification over a wide range of structurally diverse esters and alcohols without disturbing functional groups. In addition, the use of iron beta-diketonate complexes as catalysts is more environmentally friendly, safer, and economical than other transition-metal catalysts. Preliminary mechanistic studies indicate that the active catalyst is likely a dimeric mu-alkoxy-bridged iron(III) species, as determined by X-ray crystallography of [Fe(dbm)(2)(O-n-Bu)](2) derived from the alcoholysis of Fe(dbm)(3) under alkaline conditions. (C) 2011 Elsevier Ltd. All rights reserved.
• Diastereoselective oxidative α-amination of aliphatic aldehydes catalyzed by iodine: synthesis of syn-γ-hydroxy-α-amino acetals
  作者：Yun-Xiao Zhang、An-Qi Zhang、Jie-Sheng Tian、Teck-Peng Loh

  DOI：10.1039/c3ob42043d

  日期：——

  Aldehydes can react with secondary amines to give α-amino acetals via the α-amination of aliphatic aldehydes catalyzed by iodine. The presence of an asymmetric hydroxylated center at the γ-position of the aldehyde was found to induce the stereoselective amino group. This method represents a stereoselective α-amination of γ-hydroxyaldehydes for the synthesis of syn-γ-hydroxy-α-amino acetals in good

  醛可以与仲胺反应，得到α -氨基缩醛经由通过碘催化脂族醛的α-胺化。发现在醛的γ-位上存在不对称羟基化中心可诱导立体选择性氨基。该方法代表了γ-羟基醛的立体选择性α-胺化反应，用于在非常温和的条件下以良好的收率和合理的非对映选择性合成合成-γ-羟基-α-氨基乙缩醛。