(S)-tert-butyl 4-((1H-indol-3-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate | 468727-31-3

• 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: (S)-tert-butyl 4-((1H-indol-3-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: (S)-3-Boc-4-[(3-indolyl)methyl]-2,2-dimethyloxazolidine；tert-butyl (4S)-4-(1H-indol-3-ylmethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 468727-31-3
• 化学式: C₁₉H₂₆N₂O₃
• 分子量: 330.427
• InChiKey: YETTVRMOCAVXCG-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯磺酰氯 、 (S)-tert-butyl 4-((1H-indol-3-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到tert-butyl (S)-2,2-dimethyl-4-((1-(phenylsulfonyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate
  参考文献：
  名称：

  Tetrasubstituted pyridines as potent and selective AKT inhibitors: Reduced CYP450 and hERG inhibition of aminopyridines

  摘要：

  The synthesis and evaluation of tetrasubstituted aminopyridines, bearing novel azaindazole hinge binders, as potent AKT inhibitors are described. Compound 14c was identified as a potent AKT inhibitor that demonstrated reduced CYP450 inhibition and an improved developability profile compared to those of previously described trisubstituted pyridines. It also displayed dose-dependent inhibition of both phosphorylation of GSK3b and tumor growth in a BT474 tumor xenograft model in mice. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.061
• 作为产物：
  描述：

  L-色氨酸 在 甲醇 、 乙酰氯 作用下， 生成 (S)-tert-butyl 4-((1H-indol-3-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of a fully protected (2S,3R)-N-(1′,1′-dimethyl-2′- propenyl)-3-hydroxytryptophan from tryptophan

  摘要：

  (2S,3R)-N-(1',1'-二甲基-2'-丙烯基)-3-羟基色氨酸，是抗炎环肽cyclomarin C中的关键氨基酸，已从L-色氨酸首次通过全保护立体选择性地合成。© 2002 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0040-4039(02)01043-2

文献信息

• Total synthesis of tryprostatins A and B
  作者：Takayuki Yamakawa、Eiji Ideue、Yuzo Iwaki、Ayumu Sato、Hidetoshi Tokuyama、Jun Shimokawa、Tohru Fukuyama

  DOI：10.1016/j.tet.2011.05.112

  日期：2011.9

  Three distinct synthetic routes to the 2-prenyl tryptophan core skeleton of tryprostatins and their total syntheses are described. The strategies include a traditional gramine-mediated coupling reaction, Fürstner indole synthesis, and our radical-mediated indole synthesis from o-alkenylphenyl isocyanide. The establishment of reliable conditions for the radical-mediated construction of indoles via a

  描述了三种不同的合成途径，它们连接到胰前列腺素的2-异戊二烯色氨酸核心骨架及其总合成物上。该策略包括传统的禾本科胺介导的偶联反应，Fürstner吲哚合成，以及我们由邻烯基苯基异氰酸酯进行的自由基介导的吲哚合成。通过低温自由基引发剂V-70（2,2'-偶氮二（4-甲氧基-2,4-二甲基戊腈））为吲哚进行自由基介导的结构的建立建立可靠的条件导致了Tryprostatins的高效合成A和B。
• Total Synthesis of Tryprostatins A and B
  作者：Takayuki Yamakawa、Eiji Ideue、Jun Shimokawa、Tohru Fukuyama

  DOI：10.1002/anie.201004963

  日期：2010.11.22

  A reasonable approach to the radical: The establishment of reliable conditions for the radical‐mediated construction of indoles enabled the highly efficient synthesis of tryprostatins A and B. Use of the radical initiator 2,2′‐azobis(4‐methoxy‐2,4‐dimethylvaleronitrile) has allowed to carry out the radical cyclization at just 30 °C, thereby suppressing the formation of by‐products.

  自由基的合理方法：为吲哚进行自由基介导的构建建立可靠的条件，可以高效合成Tryprostatins A和B。自由基引发剂2,2'-偶氮二（4-甲氧基-2,4）的使用-二甲基戊腈）可以在30°C的温度下进行自由基环化，从而抑制了副产物的形成。
• Tetrasubstituted pyridines as potent and selective AKT inhibitors: Reduced CYP450 and hERG inhibition of aminopyridines
  作者：Hong Lin、Dennis S. Yamashita、Ren Xie、Jin Zeng、Wenyong Wang、Jack Leber、Igor G. Safonov、Sharad Verma、Mei Li、Louis LaFrance、Joseph Venslavsky、Dennis Takata、Juan I. Luengo、Jason A. Kahana、Shuyun Zhang、Kimberly A. Robell、Dana Levy、Rakesh Kumar、Anthony E. Choudhry、Michael Schaber、Zhihong Lai、Barry S. Brown、Brian T. Donovan、Elisabeth A. Minthorn、Kristin K. Brown、Dirk A. Heerding

  DOI：10.1016/j.bmcl.2009.11.061

  日期：2010.1

  The synthesis and evaluation of tetrasubstituted aminopyridines, bearing novel azaindazole hinge binders, as potent AKT inhibitors are described. Compound 14c was identified as a potent AKT inhibitor that demonstrated reduced CYP450 inhibition and an improved developability profile compared to those of previously described trisubstituted pyridines. It also displayed dose-dependent inhibition of both phosphorylation of GSK3b and tumor growth in a BT474 tumor xenograft model in mice. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of a fully protected (2S,3R)-N-(1′,1′-dimethyl-2′- propenyl)-3-hydroxytryptophan from tryptophan
  作者：Shi-Jun Wen、Hong-Wang Zhang、Zhu-Jun Yao

  DOI：10.1016/s0040-4039(02)01043-2

  日期：2002.7

  (2S,3R)-N-(1',1'-Dimethyl-2'-propenyl)-3-hydroxytryptophan, a key amino acid of the anti-inflammatory cyclic peptide, cyclomarin C, has been synthesized stereoselectively, With full protection, from L-tryptophan for the first time. (C) 2002 Elsevier Science Ltd. All rights reserved.

  (2S,3R)-N-(1',1'-二甲基-2'-丙烯基)-3-羟基色氨酸，是抗炎环肽cyclomarin C中的关键氨基酸，已从L-色氨酸首次通过全保护立体选择性地合成。© 2002 Elsevier Science Ltd. 保留所有权利。