rac-3-(1H-indol-3-yl)-2-(benzoylamino)propionic acid methyl ester | 104331-05-7

• 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: rac-3-(1H-indol-3-yl)-2-(benzoylamino)propionic acid methyl ester
• 英文别名: α-benzamido-β-(3-indolyl) propionate de methyle；Bz-Trp-OMe；rac-N-benzoyl-tryptophan methyl ester；N-benzoyl-tryptophan methyl ester；Benzoyl-tryptophanmethylester；Methyl benzoyltryptophanate；methyl 2-benzamido-3-(1H-indol-3-yl)propanoate
• CAS: 104331-05-7
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: WGDLCGXLYAWHCR-UHFFFAOYSA-N

物化性质

• 沸点：
  604.8±50.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rac-3-(1H-indol-3-yl)-2-(benzoylamino)propionic acid methyl ester 以 氢氧化钾 为溶剂， 以70%的产率得到DL-色氨酸
  参考文献：
  名称：

  合成在β位带有多个取代基的吲哚的一般方法及其在合成l-色氨酸中的应用

  摘要：

  已经利用α-甲氧基化酰胺，内酰胺，氨基甲酸酯和磺酰胺作为关键中间体，开发了β-取代的吲哚如吲哚乙酸，色胺和L-色氨酸的一般合成方法。

  DOI：

  10.1016/s0040-4039(00)81629-9
• 作为产物：
  描述：

  DL-色氨酸 在 氯化亚砜 、 氨 、 sodium carbonate 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 rac-3-(1H-indol-3-yl)-2-(benzoylamino)propionic acid methyl ester
  参考文献：
  名称：

  Lakhlifi, Takar; An, Nguyen Dinh; Schmitt, Gerard, Bulletin des Societes Chimiques Belges, 1994, vol. 103, # 4, p. 169 - 176

  摘要：

  DOI：

文献信息

• A new method for the preparation of 3,4-dihydro - and 1,2,3,4-tetrahydro-.BETA.-carbolines.
  作者：AKIHIKO ISHIDA、TOHRU NAKAMURA、KUNIHIKO IRIE、TOKURO OHISHI

  DOI：10.1248/cpb.33.3237

  日期：——

  N-Alkylthiocarbonyltryptophan (2a-i) and tryptamine (2j-m) derivatives can be converted into the corresponding 3, 4-dihydro-β-carbolines (3) under mild conditions by the use of alkylating or acylating agents. The NaBH4 reduction of 1, 3-disubstituted 3, 4-dihydro-β-carbolines (3a-i) gave cis- (5) or trans-1, 2, 3, 4-tetrahydro-β-carbolines (6) with satisfactory stereoselectivity. The synthesis of optically active 3a, b and 5a, b is also described.

  N-烷基硫羰基色氨酸（2a-i）和色氨酸（2j-m）衍生物可以在温和条件下通过烷基化或酰基化剂转化为相应的3, 4-二氢-β-氨基吲哚（3）。1, 3-二取代的3, 4-二氢-β-氨基吲哚（3a-i）经过NaBH4还原，得到了具有满意立体选择性的顺式（5）或反式-1, 2, 3, 4-四氢-β-氨基吲哚（6）。本文还描述了外消旋活性3a, b和5a, b的合成。
• Mild Reductive Cleavage of Tryptophan and Histidine Side-Chain Protecting Groups
  作者：Hernani L. S. Maia、Luís S. Monteiro、Joana Sebastião

  DOI：10.1002/1099-0690(200105)2001:10<1967::aid-ejoc1967>3.0.co;2-x

  日期：2001.5

  The activation potentials of the p-toluenesulfonyl and benzoyl groups as determined by cyclic voltammetry when they are linked to indole or imidazole are less negative than when these groups are linked to aliphatic amines. This makes them most suitable for side-chain protection of tryptophan and histidine, as it allows mild selective cleavage not only by controlled-potential electrolysis but also by

  当对甲苯磺酰基和苯甲酰基与吲哚或咪唑相连时，通过循环伏安法测定的对甲苯磺酰基和苯甲酰基的活化电位比这些基团与脂肪胺相连时的负性小。这使它们最适合色氨酸和组氨酸的侧链保护，因为它不仅可以通过控制电位电解而且可以通过使用无水甲醇中的镁或汞活化的铝进行化学还原来进行温和的选择性裂解。
• A MILD AND EFFICIENT METHOD FOR RACEMIZATION OF α-AMINO ESTERS
  作者：Uma Ramachandran、Sudhanshu Kumar、H. P. S. Chawla

  DOI：10.1080/00304940309355363

  日期：2003.12
• Intramolecular Alkylation of Aromatic Compounds XXXVI [1]. Stereoselective Synthesis of C/D-cis-Configured Ergolines
  作者：Eberhard Reimann、Wolfgang Erdle、Eugen Hargasser、Hermann Lotter

  DOI：10.1007/s007060200071

  日期：2002.7

  The stereoselective synthesis of cis-ergoline is presented. Starting from rac-N-benzoyl tryptophan methyl ester, the key compound indolinylmethylpyridin-3-one was prepared via a seven-step reaction in good yield. Since its cyclization to the desired ergolinone failed, the key compound was reduced to yield the two diastereomeric pyridin-3-ols; only one of them cyclized in trifluoromethanesulfonic acid, affording cis-ergoline. Catalytic hydrogenation of the latter gave N,N'-dimethyldihydroergoline, the X-ray crystallography of which revealed both the correct structure and identical relative configurations at C-5a and C-6a (SS or RR). Hydroboration and subsequent perruthenate oxidation of the Delta(9)-ergoline provided access to the regioisomeric ergolinols and ergolinones.
• Oikawa,Y. et al., Heterocycles, 1979, vol. 12, p. 1457 - 1462
  作者：Oikawa,Y. et al.

  DOI：——

  日期：——