Tert-butyl 2-(benzhydrylideneamino)-2-oxoacetate | 126181-27-9

• 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: Tert-butyl 2-(benzhydrylideneamino)-2-oxoacetate
• CAS: 126181-27-9
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: JOUVBXREOSUACJ-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 °C
• 沸点：
  425.4±28.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-(benzhydrylideneamino)-2-oxoacetate 在 palladium diacetate 、 18-冠醚-6 、 sodium hydride 、 三乙基硼氢化锂 、 potassium carbonate 、 (2S,4S)-4-二苯基膦-2-(二苯基膦甲基)-N-叔丁氧羰基-吡咯烷 作用下， 以 乙腈 为溶剂， 反应 10.25h， 生成 (S)-3-(Benzhydrylidene-amino)-2-benzyl-2-methoxycarbonyl-succinic acid 4-tert-butyl ester 1-methyl ester
  参考文献：
  名称：

  Preparation of optically active β-carboxyaspartic acid derivatives via Pd(0)-catalyzed asymmetric substitution of Schiff base acetates

  摘要：

  Optically active beta-carboxyaspartic acid derivative 6 (77% ee) was obtained in 48% total yield from the coupling of Schiff base acetate 3 with sodium dimethyl malonate in the presence of 5% Pd(OAc)(2)-(2S,4S)-BPPM followed by a single recrystallization. Phase-transfer catalyzed alkylation of malonates 6 affords beta-substituted ASA derivatives 7 in excellent yield without racemization at the alpha-carbon. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00048-1
• 作为产物：
  描述：

  二苯甲酮亚胺 、 2-氯-2-氧代乙酸叔丁酯 在 2,3,5-三甲基吡啶 作用下， 以 乙醚 为溶剂， 反应 0.17h， 以89%的产率得到Tert-butyl 2-(benzhydrylideneamino)-2-oxoacetate
  参考文献：
  名称：

  α-酮氨基酸衍生物的制备和Wittig反应

  摘要：

  DOI：

  10.1016/s0040-4039(00)94358-2

文献信息

• New synthesis of DL-α- aminoacids from t-butyl N(diphenylmethylene) oxamate
  作者：J.P. Bazureau、D. Person、M. Le Corre

  DOI：10.1016/s0040-4039(00)99404-8

  日期：1989.1
• Efficient Catalytic Enantioselective Reaction of a Glycine Cation Equivalent with Malonate Anions <i>via</i> Palladium Catalysis
  作者：Martin J. O'Donnell、Ning Chen、Changyou Zhou、Angela Murray、Clifford P. Kubiak、Fan Yang、George G. Stanley

  DOI：10.1021/jo961869w

  日期：1997.6.13

  The enantioselective alkylation of Schiff base acetates 1 with malonate types of stabilized carbon nucleophiles in the presence of a stable palladium source Pd(OAc)(2) and the chiral ligand (+)-BINAP was developed. The product 2, a protected beta-carboxyaspartic acid (ASA), was obtained in up to 85% enantiomeric excess by varying the ester protecting group on the substrate. The nature of the nucleophile has a significant effect on the enantioselectivity in this (2-aza-pi-allyl)palladium system. While a rapid chemical conversion was achieved with Schiff base benzoates 5, the enantioselectivity was insensitive to the leaving group used. An optically active substrate (51% ee) gave the same level of enantioselectivity as that obtained from the racemate. Temperature effects on the reaction were also studied; the best selectivity was obtained at 0 degrees C. A laboratory-scale reaction of the reactive nucleophile KCH(COOCH3)(2) with the tert-butyl ester substrate 1c gave, following a single recrystallization, product 2c with 95.5% ee in an overall chemical yield of 62%.
• BAZUREAU, J. P.;PERSON, D.;LE, CORRE M., TETRAHEDRON LETT., 30,(1989) N3, C. 3065-3068
  作者：BAZUREAU, J. P.、PERSON, D.、LE, CORRE M.

  DOI：——

  日期：——
• ODONNELL, MARTIN J.;ARASAPPAN, ASHOK;HORNBACK, WILLIAM J.;HUFFMAN, JOHN C+, TETRAHEDRON LETT., 31,(1990) N, C. 157-160
  作者：ODONNELL, MARTIN J.、ARASAPPAN, ASHOK、HORNBACK, WILLIAM J.、HUFFMAN, JOHN C+

  DOI：——

  日期：——
• Preparation and Wittig reactions of an α-keto amino acid derivative
  作者：Martin J. O'Donnell、Ashok Arasappan、William J. Hornback、John C. Huffman

  DOI：10.1016/s0040-4039(00)94358-2

  日期：1990.1