(E)-3-(3-(tert-butyl)phenyl)acrylaldehyde | 861229-29-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (E)-3-(3-(tert-butyl)phenyl)acrylaldehyde
• 英文别名: 3-tert-butylcinnamaldehyde；3-(3-Tert-butylphenyl)prop-2-enal；(E)-3-(3-tert-butylphenyl)prop-2-enal
• CAS: 861229-29-0
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: GJTGURRFVXNEQK-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  叔丁基苯 、 丙烯醛 在 palladium diacetate 氧气 、 sodium carbonate 、 乙酰丙酮 作用下， 以 丙酸 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 (E)-3-(3-(tert-butyl)phenyl)acrylaldehyde 、 (E)-3-(4-(tert-butyl)phenyl)acrylaldehyde
  参考文献：
  名称：

  Oxidative Coupling of Benzenes with α,β-Unsaturated Aldehydes by the Pd(OAc)₂/Molybdovanadophosphoric Acid/O₂ System

  摘要：

  The oxidative coupling reaction of benzene with an (x,P-unsaturated aldehyde was examined by the combined catalytic system of Pd(OAc)(2) with molybdovanadophosphoric acid (HPMoV) under atmospheric dioxygen. Thus, the reaction of benzene with acrolein under dioxygen (1 atm) by the use of catalytic amounts of Pd(OAc)(2) and H4PMo11VO40 (.) 26H(2)O in the presence of dibenzoylmethane as, a ligand in propionic acid at 90 degrees C for 1.5 h afforded cinnamaldehyde in 59% yield and beta-phenyleinnamaldehyde in 5% yield. This catalytic system was extended to the direct oxidative coupling through the C-H bond activation of various arenes with acrolein and methacrolein.

  DOI：

  10.1021/jo050534o

文献信息

• Isomeric mixture of meta and para tertio-butylphenyl propanal and production thereof
  申请人：O'Laughlin Industries, Co. Ltd.

  公开号：EP2233556A1

  公开（公告）日：2010-09-29

  A product of p-tert-butylphenyl propionaldehyde and m-tert-butylphenyl propionaldehyde, wherein m-tert-butylphenyl propionaldehyde is in an amount from 6% to 60% of the combination of p-tert-butylphenyl propionaldehyde and m-tert-butylphenyl propionaldehyde. Also a method including; adding dropwise an aldehyde solution to a basic solution; and, collecting a fraction of p-tert-butyl cinnamic aldehyde m-tert-butyl cinnamic aldehyde therefrom; and, adding a transition metal catalyst to a solution of the p-tert-butyl cinnamic aldehyde in ethanol, and, collecting therefrom by distillation a product ofp-tert-butylphenyl propionaldehyde and the meta isomer m-tert-butylphenyl propionaldehyde; wherein the product comprises m-tert-butylphenyl propionaldehyde in an amount from 6% to 60% of the combination of p-tert-butylphenyl propionaldehyde and m-tert-butylphenyl propionaldehyde.

  一种由对叔丁基苯丙醛和间叔丁基苯丙醛生成的产品，其中间叔丁基苯丙醛的含量在对叔丁基苯丙醛和间叔丁基苯丙醛的组合中为6%至60%。另外，一种方法包括：将醛溶液滴加到碱性溶液中；收集其中的对叔丁基肉桂醛和间叔丁基肉桂醛的部分；将过渡金属催化剂加入对叔丁基肉桂醛在乙醇中的溶液中，并通过蒸馏从中收集一种由对叔丁基苯丙醛和间异构体间叔丁基苯丙醛生成的产品；其中该产品包含的间叔丁基苯丙醛的含量在对叔丁基苯丙醛和间叔丁基苯丙醛的组合中为6%至60%。
• Propanal Production Methods
  申请人：Gao Zhiguo

  公开号：US20100256421A1

  公开（公告）日：2010-10-07

  A product of p-tert-butylphenyl propionaldehyde and m-tert-butylphenyl propionaldehyde, wherein m-tert-butylphenyl propionaldehyde is in an amount from 6% to 60% of the combination of p-tert-butylphenyl propionaldehyde and m-tert-butylphenyl propionaldehyde. Also a method including; adding dropwise an aldehyde solution to a basic solution; and, collecting a fraction of p-tert-butyl cinnamic aldehyde m-tert-butyl cinnamic aldehyde therefrom; and, adding a transition metal catalyst to a solution of the p-tert-butyl cinnamic aldehyde in ethanol, and, collecting therefrom by distillation a product of p-tert-butylphenyl propionaldehyde and the meta isomer m-tert-butylphenyl propionaldehyde; wherein the product comprises m-tert-butylphenyl propionaldehyde in an amount from 6% to 60% of the combination of p-tert-butylphenyl propionaldehyde and m-tert-butylphenyl propionaldehyde.

  一种由对叔丁基苯基丙醛和间叔丁基苯基丙醛制成的产品，其中间叔丁基苯基丙醛在p-叔丁基苯基丙醛和间叔丁基苯基丙醛的组合中占6%至60%的比例。还包括一种方法：将醛溶液滴加到碱性溶液中；收集p-叔丁基肉桂醛和间叔丁基肉桂醛的部分；将过渡金属催化剂加入乙醇中p-叔丁基肉桂醛的溶液中，并通过蒸馏从中收集一种由对叔丁基苯基丙醛和间异构体间叔丁基苯基丙醛制成的产品；其中该产品包含的间叔丁基苯基丙醛在p-叔丁基苯基丙醛和间叔丁基苯基丙醛的组合中占6%至60%的比例。
• Dehydrogenative β-Arylation of Saturated Aldehydes Using Transient Directing Groups
  作者：Xing-Long Zhang、Gao-Fei Pan、Xue-Qing Zhu、Rui-Li Guo、Ya-Ru Gao、Yong-Qiang Wang

  DOI：10.1021/acs.orglett.9b00695

  日期：2019.4.19

  An unprecedented cross-dehydrogenative-coupling (CDC) reaction of saturated aldehyde beta-C-H with arenes to form cinnamaldehydes via the cleavages of four C-H bonds has been developed. The reaction possesses complete E-stereoselectivity for the C = C double bond. The protocol is featured by atom and step economy, mild reaction conditions, and convenient operation.