O-allyl 2-(2-bromobenzylideneamino)-2,2-diphenylacetate | 1086429-63-1

• 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: O-allyl 2-(2-bromobenzylideneamino)-2,2-diphenylacetate
• CAS: 1086429-63-1
• 化学式: C₂₄H₂₀BrNO₂
• 分子量: 434.332
• InChiKey: SWNNUDISTWFQGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  O-allyl 2-(2-bromobenzylideneamino)-2,2-diphenylacetate 在 四(三苯基膦)钯 、 silver sulfate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.16h， 以85%的产率得到C₂₃H₁₉N
  参考文献：
  名称：

  One-Pot Tandem Decarboxylative Allylation−Heck Cyclization of Allyl Diphenylglycinate Imines: Rapid Access to Polyfunctionalized 1-Aminoindanes

  摘要：

  1-Aminoindanes are generated from allyl diphenylglycinate imines employing a "one-pot" palladium-catalyzed decarboxylative allylation-Heck cyclization cascade. Variation of both the aryl and allyl moieties leads to a diverse range of polycyclic imines, amenable to the synthesis of natural products and other biologically relevant small molecules.

  DOI：

  10.1021/ol801986m
• 作为产物：
  描述：

  allyl 2,2-diphenylglycinate 、 邻溴苯甲醛 以 苯 为溶剂， 反应 27.0h， 以75%的产率得到O-allyl 2-(2-bromobenzylideneamino)-2,2-diphenylacetate
  参考文献：
  名称：

  One-Pot Tandem Decarboxylative Allylation−Heck Cyclization of Allyl Diphenylglycinate Imines: Rapid Access to Polyfunctionalized 1-Aminoindanes

  摘要：

  1-Aminoindanes are generated from allyl diphenylglycinate imines employing a "one-pot" palladium-catalyzed decarboxylative allylation-Heck cyclization cascade. Variation of both the aryl and allyl moieties leads to a diverse range of polycyclic imines, amenable to the synthesis of natural products and other biologically relevant small molecules.

  DOI：

  10.1021/ol801986m

文献信息

• Nickel-Catalyzed Decarboxylative Generation and Asymmetric Allylation of 2-Azaallyl Anions
  作者：Chenlu Liu、Changfeng Deng、Han Yang、Xiaoyan Qian、Shaojian Tang、Michal Poznik、Jason J. Chruma

  DOI：10.1021/acs.joc.9b01293

  日期：2019.8.16

  The first nickel-catalyzed asymmetric decarboxylative allylation (DcA) of allyl 2,2-diarylglycinate imines is reported. This transformation utilizes a chiral ferrocenyl bidentate ligand and a Ni(0) precatalyst to mediate the decarboxylative generation and asymmetric allylation of 2-azaallyl anions, affording α-aryl homoallylic imines in modest-to-high yields and moderate-to-high enantiomeric ratios

  报道了2，2-二芳基甘氨酸烯丙基烯丙基亚胺的第一个镍催化的不对称脱羧烯丙基化（DcA）。此转化利用手性二茂铁二齿双齿配体和Ni（0）预催化剂介导2-氮杂烯丙基阴离子的脱羧生成和不对称烯丙基化，以中等至高收率和中等至高对映体比率提供α-芳基均烯丙基亚胺。 。与我们先前报道的类似的Pd介导的实验方案相比，所产生的Ni催化的转化过程被证明不那么普遍，但是就C–C键形成的区域和对映选择性而言，它仍然表现出一定的优势。
• Tandem C−C Bond-Forming Processes: Interception of the Pd-Catalyzed Decarboxylative Allylation of Allyl Diphenylglycinate Imines with Activated Olefins
  作者：Andrew A. Yeagley、Melissa A. Lowder、Jason J. Chruma

  DOI：10.1021/ol901745x

  日期：2009.9.3

  Interception of the Pd-catalyzed decarboxylative allylation of allyl diphenylglycinate Imines with appropriately functionalized Michael acceptors, followed by Heck cyclization, allows for the efficient construction of relatively complex organoamine frameworks in one reaction vessel. The initial intercepted decarboxylative allylation Is remarkably insensitive toward solvent and catalyst, typically proceeding under ambient conditions.