N-benzyloxycarbonyl tryptophan methyl ester | 86961-55-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-benzyloxycarbonyl tryptophan methyl ester
• 英文别名: benzyl 3-[(2S)-2-amino-3-methoxy-3-oxopropyl]indole-1-carboxylate
• CAS: 86961-55-9
• 化学式: C₂₀H₂₀N₂O₄
• 分子量: 352.39
• InChiKey: BUOHWIFKHJDMSI-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl tryptophan methyl ester 在 碳酸氢钠 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  AgNTf2-Mediated Arylation of Bromopyrroloindolines

  摘要：

  The silver(I)-mediated arylation of bromopyrroloindolines was developed. The selection of silver salts was crucial to obtain arylated compounds in high yields. Among the various tested silver(I) salts, AgNTf2 was the most effective agent for arylation. Reactions using various electron-rich aromatic compounds revealed that the developed conditions are suitable for the arylation of a broad range of aromatic compounds, including benzene derivatives, furan, thiophene, and pyrrole.

  DOI：

  10.3987/com-17-13777
• 作为产物：
  描述：

  N-[叔丁氧羰基]-L-色氨酸甲酯 在 四丁基硫酸氢铵 、 三氟乙酸 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 N-benzyloxycarbonyl tryptophan methyl ester
  参考文献：
  名称：

  AgNTf2-Mediated Arylation of Bromopyrroloindolines

  摘要：

  The silver(I)-mediated arylation of bromopyrroloindolines was developed. The selection of silver salts was crucial to obtain arylated compounds in high yields. Among the various tested silver(I) salts, AgNTf2 was the most effective agent for arylation. Reactions using various electron-rich aromatic compounds revealed that the developed conditions are suitable for the arylation of a broad range of aromatic compounds, including benzene derivatives, furan, thiophene, and pyrrole.

  DOI：

  10.3987/com-17-13777

文献信息

• Oxidative Amidation of Nitroalkanes with Amine Nucleophiles using Molecular Oxygen and Iodine
  作者：Jing Li、Martin J. Lear、Yuya Kawamoto、Shigenobu Umemiya、Alice R. Wong、Eunsang Kwon、Itaru Sato、Yujiro Hayashi

  DOI：10.1002/anie.201505192

  日期：2015.10.26

  encumberance, and epimerizable stereocenters. A direct oxidative method was developed to form amide and peptide bonds between amines and primary nitroalkanes simply by using I2 and K2CO3 under O2. Contrary to expectations, a 1:1 halogen‐bonded complex forms between the iodonium source and the amine, which reacts with nitronates to form α‐iodo nitroalkanes as precursors to the amides.

  酰胺和肽的形成通常需要强大而温和的试剂系统。然而，所使用的试剂通常是昂贵且高度复杂的。达到这些目标的新的原子经济和实用的方法是非常可取的。理想情况下，该方法应从易于以手性和非手性形式获得的底物开始，并使用廉价的试剂，这些试剂与多种官能团，空间位阻和可差向立体中心兼容。开发了一种直接氧化方法，只需在O 2下使用I 2和K 2 CO 3即可在胺与伯硝基烷烃之间形成酰胺和肽键。。与预期相反，在碘鎓源和胺之间形成了1：1的卤素键合配合物，该配合物与硝酸盐反应生成α-碘硝基烷烃，作为酰胺的前体。
• Asymmetric synthesis of indolo[2,3-a]quinolizidin-2-ones - congeners to yohimbine-type alkaloids
  作者：Herbert Waldmann、auMatthias Braun、Markus Weymann、Markus Gewehr

  DOI：10.1016/s0040-4020(01)80309-4

  日期：1993.1

  Schiff bases derived from tryptophan methyl ester and tryptamine react with Danishefkys diene in the presence of ZnCl2 to give enaminones which are subsequently transformed into indolo[2,3-a]quinolizidin-2-ones by acid-catalyzed cyclization. These tetracyclic aminoketones serve as viable intermediates in the construction of complex alkaloids, e. g. reserpine and deserpidine, and analogues thereof.
• AgNTf2-Mediated Arylation of Bromopyrroloindolines
  作者：Hidetoshi Tokuyama、Soichiro Sato、Azusa Hirayama、Tohma Adachi、Daichi Kawauchi、Hirofumi Ueda

  DOI：10.3987/com-17-13777

  日期：——

  The silver(I)-mediated arylation of bromopyrroloindolines was developed. The selection of silver salts was crucial to obtain arylated compounds in high yields. Among the various tested silver(I) salts, AgNTf2 was the most effective agent for arylation. Reactions using various electron-rich aromatic compounds revealed that the developed conditions are suitable for the arylation of a broad range of aromatic compounds, including benzene derivatives, furan, thiophene, and pyrrole.