Benzyl 3-[2-(phenylmethoxycarbonylamino)ethyl]indole-1-carboxylate | 258883-21-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Benzyl 3-[2-(phenylmethoxycarbonylamino)ethyl]indole-1-carboxylate
• CAS: 258883-21-5
• 化学式: C₂₆H₂₄N₂O₄
• 分子量: 428.488
• InChiKey: GJHUGIUUONLNPV-UHFFFAOYSA-N

物化性质

• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzyl 3-[2-(phenylmethoxycarbonylamino)ethyl]indole-1-carboxylate 在 偶氮二异丁腈 、 三正丁基氢锡 、 对甲苯磺酸 、 丙烯酸甲酯（MA） 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (3aR,8aS)-2,3,3a,8a-Tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid dibenzyl ester
  参考文献：
  名称：

  Total Synthesis of 5-N-Acetylardeemin and Amauromine:  Practical Routes to Potential MDR Reversal Agents

  摘要：

  The total synthesis of the title compounds has been accomplished. The key step involves the kinetic stereoselective conversion of 19 --> 20. The synthesis of 20 represents for the first time a direct method for constructing exo-pyrroloindoles from protected tryptophans in a highly diastereoselective manner. This step was followed by reverse prenylation (see conversion of 20 --> 27). Using the methodology worked out for the titled compounds, a practical synthesis of several promising MDR reversal agents was possible. Biological data that provided the basis for selection of candidates for advanced study are presented. Preliminary profiling of the zones of the molecules that are responsive to changes while still retaining MDR reversal ability are described. On the basis of these findings, compounds 2, 50, and 51 were selected for more extensive biological follow-up.

  DOI：

  10.1021/ja991558d
• 作为产物：
  描述：

  色胺 、 氯甲酸苄酯 在 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到Benzyl 3-[2-(phenylmethoxycarbonylamino)ethyl]indole-1-carboxylate
  参考文献：
  名称：

  Total Synthesis of 5-N-Acetylardeemin and Amauromine:  Practical Routes to Potential MDR Reversal Agents

  摘要：

  The total synthesis of the title compounds has been accomplished. The key step involves the kinetic stereoselective conversion of 19 --> 20. The synthesis of 20 represents for the first time a direct method for constructing exo-pyrroloindoles from protected tryptophans in a highly diastereoselective manner. This step was followed by reverse prenylation (see conversion of 20 --> 27). Using the methodology worked out for the titled compounds, a practical synthesis of several promising MDR reversal agents was possible. Biological data that provided the basis for selection of candidates for advanced study are presented. Preliminary profiling of the zones of the molecules that are responsive to changes while still retaining MDR reversal ability are described. On the basis of these findings, compounds 2, 50, and 51 were selected for more extensive biological follow-up.

  DOI：

  10.1021/ja991558d

文献信息

• An extension of nickel-catalyzed reductive coupling between tertiary alkyl halides with allylic carbonates
  作者：Yingying Yu、Haifeng Chen、Qun Qian、Ken Yao、Hegui Gong

  DOI：10.1016/j.tet.2018.07.057

  日期：2018.9

  The nickel catalyzed reductive coupling of allylic carbonates with chloro-cyclotryptamine analogs to construct sterically congested all C(sp3) quaternary centers has been achieved with emphasis on the substrate scope. And the using of dienyl methyleneyl carbonates coupling with a variety of tertiary alkyl halides furnished the dienylated products improved the reaction's applicability.

  镍催化的烯丙基碳酸酯与氯-环色胺类似物的还原催化偶联，以建立空间上所有C（sp 3）四元中心的拥挤，并着重于底物范围。并且使用碳酸二烯基亚甲基酯与各种叔烷基卤化物偶合，提供了二烯基化产物，提高了反应的适用性。
• Organocatalytic asymmetric selenofunctionalization of tryptamine for the synthesis of hexahydropyrrolo[2,3-<i>b</i>]indole derivatives
  作者：Qiang Wei、Ya-Yi Wang、Yu-Liu Du、Liu-Zhu Gong

  DOI：10.3762/bjoc.9.177

  日期：——

  A chiral phosphoric acid-catalyzed selenofunctionalization of tryptamine derivatives provides access to 3a-(phenylselenyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole derivatives in high yields and with synthetically useful levels of enantioselectivity (up to 89% ee).

  手性磷酸催化的色胺衍生物硒功能化提供了高产率和合成有用水平的 3a-(苯基硒基)-1,2,3,3a,8,8a-六氢吡咯并[2,3-b]吲哚衍生物对映选择性（高达 89% ee）。
• Deprotection of benzyl-derived groups via photochemically mesolytic cleavage of C–N and C–O bonds
  作者：Kangjiang Liang、Xipan Li、Delian Wei、Cuihua Jin、Chuanwang Liu、Chengfeng Xia

  DOI：10.1016/j.chempr.2022.11.001

  日期：2023.2

  easily removed via visible light irradiation under mild conditions. We found that an excited phenolate-type photocatalyst efficiently transfers an electron to the benzene ring of benzyl-derived protecting groups to generate a phenyl radical anion. The benzyl C–N or C–O bond is then mesolytically cleaved by releasing a benzyl radical. This method enables efficient deprotection of the benzyl group on amides

  苄基及其衍生物是有机合成中最常用和最广泛使用的保护基团，通常通过传统的过渡金属催化氢解或 Birch 还原来去除。氢解受到官能团相容性以及氢的易燃性和易爆性的限制，而 Birch 还原则受到易燃碱和苛刻条件的限制。在这里，我们报告在温和条件下通过可见光照射很容易去除苄基衍生的保护基团。我们发现激发的酚盐型光催化剂有效地将电子转移到苄基衍生保护基团的苯环上以产生苯基阴离子。苄基 C-N 或 C-O 键然后通过释放苄基自由基被分解裂解。该方法能够有效地脱保护酰胺、芳基胺、醚、酯和氨基甲酸酯上的苄基。具体而言，该方法在碳水化合物、肽、药物和具有多种功能的天然产物中显示出出色的化学和区域选择性。
• Total Synthesis of 5-<i>N</i>-Acetylardeemin and Amauromine:  Practical Routes to Potential MDR Reversal Agents
  作者：Kristopher M. Depew、Stephen P. Marsden、Danuta Zatorska、Andrzej Zatorski、William G. Bornmann、Samuel J. Danishefsky

  DOI：10.1021/ja991558d

  日期：1999.12.1

  The total synthesis of the title compounds has been accomplished. The key step involves the kinetic stereoselective conversion of 19 --> 20. The synthesis of 20 represents for the first time a direct method for constructing exo-pyrroloindoles from protected tryptophans in a highly diastereoselective manner. This step was followed by reverse prenylation (see conversion of 20 --> 27). Using the methodology worked out for the titled compounds, a practical synthesis of several promising MDR reversal agents was possible. Biological data that provided the basis for selection of candidates for advanced study are presented. Preliminary profiling of the zones of the molecules that are responsive to changes while still retaining MDR reversal ability are described. On the basis of these findings, compounds 2, 50, and 51 were selected for more extensive biological follow-up.