2-(Benzhydrylidene-amino)-hexa-4,5-dienoic acid methyl ester | 122885-25-0

• 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: 2-(Benzhydrylidene-amino)-hexa-4,5-dienoic acid methyl ester
• 英文别名: methyl 2-(benzhydrylideneamino)hexa-4,5-dienoate
• CAS: 122885-25-0
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: RMVMHAQXBCOLKX-UHFFFAOYSA-N

物化性质

• 沸点：
  391.5±42.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  2-(Benzhydrylidene-amino)-hexa-4,5-dienoic acid methyl ester 在 盐酸 、 氢氧化钾 、 ammonium hydroxide 、 sodium hydroxide 、 manganese(II) sulfate 、 Pseudomonas putida ATCC 12633 (whole cells,S-aminopeptidase) 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 反应 62.0h， 生成 (R)-2-{[1-Phenyl-meth-(E)-ylidene]-amino}-hexa-4,5-dienoic acid amide
  参考文献：
  名称：

  A Biocatalytic Route to Enantiomerically Pure Unsaturated α-H-α-Amino Acids

  摘要：

  DOI：

  10.1002/1615-4169(200108)343:6/7<662::aid-adsc662>3.3.co;2-9
• 作为产物：
  描述：

  4-bromo-buta-1,2-diene 、 二苯亚甲基甘氨酸甲酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-(Benzhydrylidene-amino)-hexa-4,5-dienoic acid methyl ester
  参考文献：
  名称：

  A Biocatalytic Route to Enantiomerically Pure Unsaturated α-H-α-Amino Acids

  摘要：

  DOI：

  10.1002/1615-4169(200108)343:6/7<662::aid-adsc662>3.3.co;2-9

文献信息

• Palladium-Catalyzed Synthesis of γ-Allenic α-Amino Acids
  作者：Bernard Cazes、Dariouche Djahanbini、Jacques Goré、Jean-Piere Genêt、Jean-Marc Gaudin

  DOI：10.1055/s-1988-27776

  日期：——

  γ-Allenic α-amino acids can be obtained by a three-step sequence from the phosphates of α-allenic alcohols: i) palladium-catalyzed alkylation of a Schiff base derived from glycine ester by these phosphates, ii) acidic hydrolysis of the imine functionality, and iii) saponification of the resulting amino esters.

  γ-环烯醇-α-氨基酸可以通过三步反应序列从α-环烯醇醇的磷酸盐获得：i) 以这些磷酸盐为催化剂，对由甘氨酸酯衍生的Schiff碱进行钯催化烷基化；ii) 对亚胺官能团进行酸性水解；iii) 对所得氨基酯进行皂化。
• Synthetic Study of Dragmacidin E: Construction of the Core Structure Using Pd-Catalyzed Cascade Cyclization and Rh-Catalyzed Aminoacetoxylation
  作者：Naoya Inoue、Shun-ichi Nakano、Shingo Harada、Yasumasa Hamada、Tetsuhiro Nemoto

  DOI：10.1021/acs.joc.7b00083

  日期：2017.3.3

  We developed a novel synthetic method of the core structure of dragmacidin E bearing a 7-membered ring-fused bis(indolyl)pyrazinone skeleton. Formation of the 7-membered ring-fused tricyclic indole skeleton was accomplished using a palladium-catalyzed Heck insertion–allylic amination cascade. Vicinal difunctionalization of the 7-membered ring was realized via a rhodium-catalyzed aminoacetoxylation

  我们开发了具有7元环稠合双（吲哚基）吡嗪酮骨架的drammacidin E核心结构的新型合成方法。7元环稠合的三环吲哚骨架的形成是通过钯催化的Heck插入-烯丙基胺化级联反应完成的。经由铑催化的氨基乙酰氧基化实现7元环的邻域双官能化。
• Selective Azetidine and Tetrahydropyridine Formation via Pd-Catalyzed Cyclizations of Allene-Substituted Amines and Amino Acids
  作者：Floris P. J. T. Rutjes、Kim C. M. F. Tjen、Larissa B. Wolf、Willem F. J. Karstens、Hans E. Schoemaker、Henk Hiemstra

  DOI：10.1021/ol990700c

  日期：1999.9.1

  [GRAPHICS]By choosing the right substituents either highly functionalized unusual four-membered ring amino acids or the isomeric pipecolic acid derivatives are obtained in enantiomerically pure form. Starting material is a linear allene containing amino acid that has been resolved via biocatalysis.
• Pd-Catalyzed Cascade Cyclization by Intramolecular Heck Insertion of an Allene–Allylic Amination Sequence: Application to the Synthesis of 3,4-Fused Tricyclic Indoles
  作者：Shun-ichi Nakano、Naoya Inoue、Yasumasa Hamada、Tetsuhiro Nemoto

  DOI：10.1021/acs.orglett.5b00973

  日期：2015.6.5

  A novel Pd-catalyzed cascade cyclization by intramolecular Heck insertion of an alleneallylic amination sequence was developed. Allenes tethered to ortho-iodoaniline derivatives at the meta-position were reacted with 5-10 mol % of Pd catalyst and 4 equiv of K2CO3 in DMSO at 90 degrees C, producing 3,4-fused tricyclic 3-alkylidene indoline derivatives in moderate to excellent yield. The reaction products were divergently transformed into three types of 3,4-fused tricyclic indole derivatives, successfully demonstrating the versatile properties of the reaction products.