ethyl (2-azidomethyl)phenylacetate | 428501-02-4

• 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: ethyl (2-azidomethyl)phenylacetate
• 英文别名: ethyl 2-(2-(azidomethyl)phenyl)acetate；Ethyl 2-[2-(azidomethyl)phenyl]acetate
• CAS: 428501-02-4
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: PVOUFCCAALAXDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2-azidomethyl)phenylacetate 在 草酰氯 、 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 71.5h， 生成 1-苄基-3H-吲哚-2-酮
  参考文献：
  名称：

  ω-叠氮基戊酰氯的Schmidt反应，随后进行重排离子的分子间捕获：Assoanine和相关的吡咯并菲啶生物碱的合成

  摘要：

  探索了在存在其他亲核试剂的情况下ω-叠氮基戊酰氯的Schmidt反应。证明了芳烃，醇和胺是施密特重排中异氰酸酯离子和N-酰基亚胺离子的分子间捕获剂，从而以中等至极好的收率提供了相应的产物。来自该反应的两个2-氧代吲哚被成功地转化为四种天然生物碱，即，伴生素，脱水赖氨酸，氧代伴嘌呤和脱水赖皮酮。

  DOI：

  10.1021/acs.joc.8b03018
• 作为产物：
  描述：

  3-异色酮 在 sodium azide 、 三溴化磷 作用下， 以 甲醇 、 水 为溶剂， 反应 5.5h， 生成 ethyl (2-azidomethyl)phenylacetate
  参考文献：
  名称：

  ω-叠氮基戊酰氯的Schmidt反应，随后进行重排离子的分子间捕获：Assoanine和相关的吡咯并菲啶生物碱的合成

  摘要：

  探索了在存在其他亲核试剂的情况下ω-叠氮基戊酰氯的Schmidt反应。证明了芳烃，醇和胺是施密特重排中异氰酸酯离子和N-酰基亚胺离子的分子间捕获剂，从而以中等至极好的收率提供了相应的产物。来自该反应的两个2-氧代吲哚被成功地转化为四种天然生物碱，即，伴生素，脱水赖氨酸，氧代伴嘌呤和脱水赖皮酮。

  DOI：

  10.1021/acs.joc.8b03018

文献信息

• An Intramolecular Schmidt Reaction of δ-Azido <i>N</i>-Acylbenzotriazoles
  作者：Chun-Fang Liu、Zhi-Qi Cao、Shao-Lei Ding、Jing Zhu、Peiming Gu

  DOI：10.1021/acs.orglett.1c00200

  日期：2021.2.5

  A Lewis acid promoted intramolecular Schmidt reaction of N-acylbenzotriazoles with alkyl azides was designed and realized. The benzotriazole was not only employed as an efficient activator for initiating the Schmidt rearrangement but also used as a powerful terminator for the subsequent nucleophilic trapping of the isocyanate ion and/or N-acyliminium ion from the rearrangement. Thirteen δ-azido N-acylbenzotriazoles

  设计并实现了路易斯酸促进的N-酰基苯并三唑与烷基叠氮化物的分子内Schmidt反应。苯并三唑不仅用作引发施密特重排的有效活化剂，而且还用作强力终止剂，用于随后从重排中异氰酸酯离子和/或N-酰基亚胺离子的亲核捕获。研究了十三种δ-叠氮基N-酰基苯并三唑，该转化以良好或优异的收率提供了所需的苯并三唑-1-羧酰胺和内酰胺。
• Synthesis of Isoindoles from Intramolecular Condensation of Benzyl Azides with α-Aryldiazoesters
  作者：Jing Zhu、Rui Li、Yan Su、Peiming Gu

  DOI：10.1021/acs.joc.8b03180

  日期：2019.5.3

  Rh-catalyzed intramolecular condensation of the benzyl azides with α-aryldiazoesters was explored. The reaction proceeded through the nucleophilic attack of the organic azide onto a rhodium carbenoid, while releasing nitrogen gas, affording the α-imino esters as the primary product. Tautomerization of the imino esters efficiently gave 13 desired isoindoles with good to excellent yields.

  探索了Rh催化的叠氮化物与α-芳基重氮酯的分子内缩合。反应通过有机叠氮化物对铑类胡萝卜素的亲核攻击而进行，同时释放氮气，得到α-亚氨基酯作为主要产物。亚氨基酯的互变异构有效地以良好至优异的产率得到13种所需的异吲哚。
• Ligands to the (IRAP)/AT4 receptor encompassing a 4-hydroxydiphenylmethane scaffold replacing Tyr2
  作者：Hanna Andersson、Heidi Demaegdt、Georges Vauquelin、Gunnar Lindeberg、Anders Karlén、Mathias Hallberg

  DOI：10.1016/j.bmc.2008.05.046

  日期：2008.7

  Analogues of the hexapeptide angiotensin IV (Ang IV, Val(1)-Tyr(2)-Ile(3)-His(4)-Pro(5)-Phe(6)) encompassing a 4-hydroxydiphenylmethane scaffold replacing Tyr(2) and a phenylacetic or benzoic acid moiety replacing His4-Pro5-Phe6 have been synthesized and evaluated in biological assays. The analogues inhibited the proteolytic activity of cystinyl aminopeptidase ( CAP), frequently referred to as the insulin-regulated aminopeptidase ( IRAP), and were found less efficient as inhibitors of aminopeptidase N (AP-N). The best Ang IV mimetics in the series were approximately 20 times less potent than Ang IV as IRAP inhibitors. Furthermore, it was found that the ligands at best exhibited a 140 times lower binding affinity to the membrane-bound IRAP/AT4 receptor than Ang IV. Although the best compounds still exert lower activities than Ang IV, it is notable that these compounds comprise only two amino acid residues and are considerably less peptidic in character than the majority of the Ang IV analogues previously reported as IRAP inhibitors in the literature. (c) 2008 Elsevier Ltd. All rights reserved.
• (2-Azidomethyl)phenylacetyl as a new, reductively cleavable protecting group for hydroxyl groups in carbohydrate synthesis
  作者：Jinghua Xu、Zhongwu Guo

  DOI：10.1016/s0008-6215(01)00292-0

  日期：2002.2

  The (2-azidomethyl)phenylacetyl group (AMPA) is described as a new protecting group for carbohydrates, AMPA was introduced to carbohydrate hydroxyl groups in the presence of DCC, while its removal was conveniently achieved via Lindlar catalyst-catalyzed hydrogenation that had no influence on other protecting groups including benzyl, acyl, acetal and ketal. (C) 2002 Elsevier Science Ltd. All rights reserved.