2-azido-1-(4'-methoxyphenyl)-propan-1-one | 313692-52-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-1-(4'-methoxyphenyl)-propan-1-one
• 英文别名: (±)-2-azido-1-(4-methoxyphenyl)propan-1-one；4'-methoxy-2-azidopropiophenone；2-azido-1-(4-methoxyphenyl)propan-1-one
• CAS: 313692-52-3
• 化学式: C₁₀H₁₁N₃O₂
• 分子量: 205.216
• InChiKey: SKTIVXVOVZNSBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-azido-1-(4'-methoxyphenyl)-propan-1-one 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 生成 2-氨基-1-(4-甲氧基苯基)-1-丙酮
  参考文献：
  名称：

  Initial Structure–Activity Relationship Studies of a Novel Series of Pyrrolo[1,2-a]pyrimid-7-ones as GnRH Receptor Antagonists

  摘要：

  Initial SAR studies on 1-aminomethyl-2-aryl-3-cyano-pyrrolo[1,2-a]pyrimid-7-one-6-carboxylates as human GnRH receptor antagonists were discussed. 2-(2-Methylaminoethyl)pyridine was discovered to be a key feature for generating active compounds. The best compound from the series had 25 nM (K-i) binding affinity to human GnRH receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00779-x
• 作为产物：
  描述：

  2-溴-1-(4-甲氧苯基)丙酮 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以89%的产率得到2-azido-1-(4'-methoxyphenyl)-propan-1-one
  参考文献：
  名称：

  Au（III）和Bi（III）催化的苯甲酰化反应中的动力学非对映异构体分化：2-氨基-1,1-二芳基烷烃的简明和立体控制合成

  摘要：

  携带在烷烃链的相邻α硝基或α-叠氮基苄醇被转化成顺式-1,1-二芳基-2-硝基-和2- azidoalkanes与由布朗斯台德酸和路易斯酸催化的立体选择性反应的富电子的芳烃。发现氯化金（III）和三氟甲磺酸铋（III）作为催化剂特别有效，在非对映异构体α-取代的苄醇的反应性中表现出动力学控制的差异。预计将其用于治疗相关的顺式和反式2-氨基-1,1-二芳基烷烃。

  DOI：

  10.1021/ol500902p

文献信息

• Catalytic Lewis and Brønsted acid <i>syn</i>-diastereoselective benzylic substitutions of <i>α</i>-hydroxy-<i>β</i>-nitro- and <i>α</i>-hydroxy-<i>β</i>-azido-alkyl arenes
  作者：Raphaël Hensienne、Jean-Philippe Cusson、Étienne Chénard、Stephen Hanessian

  DOI：10.1139/cjc-2020-0016

  日期：2020.6

  A series of alkyl and alkenyl p-methoxy arenes containing α,β-disubstituted diamino and amino alcohol groups were synthesized from β-nitro and β-azido benzylic alcohols in the presence of AuCl₃ as catalyst. The formation of predominantly syn-disubstituted products were rationalized on the basis of mechanistic considerations and transition state models relying on A^1,3-allylic strain. The products could have utility in the design of medicinally relevant compounds and as chiral ligands for asymmetric catalysis. A new synthesis of (+)-sertraline (Zoloft) was achieved.

  一系列含有α,β-二取代二胺和氨基醇基团的烷基和烯基对甲氧基苯被合成出来，这些化合物是从β-硝基和β-叠氮苄基醇在AuCl₃存在下作为催化剂的条件下合成的。基于机理考虑和依赖于A^1,3-烯基应变的过渡态模型，主要形成了同构二取代产物。这些产物可能在设计药用相关化合物和作为手性配体用于不对称催化方面具有实用价值。一种新的合成方法合成了（+）-去甲丙丁胺（Zoloft）。
• Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
  申请人：Neurocrine Biosciences, Inc.

  公开号：US06346534B1

  公开（公告）日：2002-02-12

  GnRH receptor antagonists are disclosed which have utility in the treatment of a variety of sex-hormone related conditions in both men and women. The compounds of this invention have the structure: including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein Ar, B, R1, R2, R3a, R3b, R4, R5, R6 and m are as defined herein.

  GnRH受体拮抗剂已被披露，可用于治疗男性和女性的各种与性激素相关的疾病。该发明的化合物具有以下结构：包括立体异构体、前药和其药用盐，其中Ar、B、R1、R2、R3a、R3b、R4、R5、R6和m的定义如本文所述。
• Estrogenic diazenes: heterocyclic non-steroidal estrogens of unusual structure with selectivity for estrogen receptor subtypes
  作者：Usha Ghosh、Deshanie Ganessunker、Viswajanani J Sattigeri、Kathryn E Carlson、Deborah J Mortensen、Benita S Katzenellenbogen、John A Katzenellenbogen

  DOI：10.1016/s0968-0896(02)00309-7

  日期：2003.2

  Estrogens regulate many biological functions, often acting in a tissue-selective manner. Their tissue-selective action is believed to involve differential estrogen action through the two estrogen receptor (ER) subtypes, ERalpha and ERbeta, as well as differential interaction of the ligand-receptor complexes with promoters and coregulator proteins. In the latter case, selectivity is based on the induction of specific conformations of the ligand-ER complex, conformations that are influenced by the structure of the ligand. Estrogen pharmaceuticals having an ideal balance of tissue-selective activity are being sought for menopausal hormone replacement, breast cancer prevention and therapy, and other actions. To expand on the structural diversity of ER ligands that might show such tissue selectivity, we have prepared a series of diazenes (pyrazines, pyrimidines, and pyridazines) substituted with two to four aryl groups and various short-chain aliphatic substituents. All of the pyrazine and pyrimidines bind to ER, some with high affinity and with a considerable degree of preferential binding to either ERalpha or ERbeta. One pyrimidine and one pyrazine have ERalpha affinity preferences as high as 23 and 9, respectively, and one pyrimidine has an ERP affinity preference of 8. The pyridazines, by contrast, are quite polar and have only very low binding affinity for the ER. In cell-based transcription assays, several of the pyrimidines and a pyrazine were found to be considerably more agonistic on ERalpha than on ERbeta. Because these triaryl diazenes have the largest volumes among the ER ligands so far investigated, their high affinity demonstrates the flexibility of the ligand binding pocket of the ERs and its tolerance for large substituents. Thus, these novel heterocyclic ligands expand the repertoire of chemical structures that bind to the estrogen receptor, and they could prove to be useful in elucidating the biological behavior of the two ER subtypes and in forming the basis for new estrogen pharmaceuticals having desirable tissue selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.
• An Effective Synthesis of α-Azido Ketones From Ketones
  作者：Jong Chan Lee、Sehyun Kim、Woo Choul Shin

  DOI：10.1080/00397910008087049

  日期：2000.12

  One-pot transformation of ketones into alpha -azido ketones has been achieved by successive treatment with HNIB and NaN3 in acetonitrile.
• IMIDAZO- AND PYRROLO[1,2-A]PYRIMID-4-ONES AS GONADOTROPIN-RELEASING HORMONE RECEPTOR ANTAGONISTS
  申请人：Neurocrine Biosciences, Inc.

  公开号：EP1185530A1

  公开（公告）日：2002-03-13