(3R)-3-氟-4-氧杂哌啶-1-羧酸叔丁酯 | 1266339-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (3R)-3-氟-4-氧杂哌啶-1-羧酸叔丁酯
• 英文名称: tert-butyl (3R)-3-fluoro-4-oxopiperidine-1-carboxylate
• 英文别名: (R)-N-Boc-3-fluoro-4-oxopiperidine；1-Boc-3R-fluoropiperidin-4-one；(+)-1-(tert-butoxycarbonyl)-3-fluoro-4-piperidone
• CAS: 1266339-10-9
• 化学式: C₁₀H₁₆FNO₃
• 分子量: 217.24
• InChiKey: JZNWQLLPLOQGOI-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  跨叔丁基-3-氟-4-羟基哌啶-1-羧酸	tert-butyl (3R,4R)-3-fluoro-4-hydroxypiperidine-1-carboxylate	1174020-43-9	C10H18FNO3	219.256
  N-叔丁氧羰基-4-哌啶酮	N-tert-butyloxycarbonylpiperidin-4-one	79099-07-3	C10H17NO3	199.25

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  (3R,4S)-3-氟-4-羟基哌啶-1-羧酸叔丁酯	tert-butyl (3R,4S)-3-fluoro-4-hydroxypiperidine-1-carboxylate	955028-88-3	C10H18FNO3	219.256

反应信息

• 作为反应物：
  描述：

  (3R)-3-氟-4-氧杂哌啶-1-羧酸叔丁酯 在 tetramethylammonium borohydride 作用下， 以 甲醇 为溶剂， 反应 4.33h， 以50%的产率得到(3R,4S)-3-氟-4-羟基哌啶-1-羧酸叔丁酯
  参考文献：
  名称：

  Enantioselective Synthesis of cis-3-Fluoropiperidin-4-ol, a Building Block for Medicinal Chemistry

  摘要：

  The first enantioselective route to both enantiomers of cis-1-Boc-3-fluoropiperidin-4-ol, a highly prized building block for medicinal chemistry, is reported. An enantioselective fluorination is employed, taking advantage of the methodology reported by MacMillan, which uses a modified cinchona alkaloid catalyst. In studying the fluorination reaction, we have shown that the catalyst can be replaced by commercially available primary amines, including α-methylbenzylamine, with similar levels of enantioselectivity. The piperidinols are readily crystallized to obtain enantiopure material.

  DOI：

  10.1021/jo401352z
• 作为产物：
  描述：

  N-叔丁氧羰基-4-哌啶酮 在 (S)-(-)- α-甲基苄胺 、 sodium carbonate 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以71%的产率得到(3R)-3-氟-4-氧杂哌啶-1-羧酸叔丁酯
  参考文献：
  名称：

  Enantioselective Synthesis of cis-3-Fluoropiperidin-4-ol, a Building Block for Medicinal Chemistry

  摘要：

  The first enantioselective route to both enantiomers of cis-1-Boc-3-fluoropiperidin-4-ol, a highly prized building block for medicinal chemistry, is reported. An enantioselective fluorination is employed, taking advantage of the methodology reported by MacMillan, which uses a modified cinchona alkaloid catalyst. In studying the fluorination reaction, we have shown that the catalyst can be replaced by commercially available primary amines, including α-methylbenzylamine, with similar levels of enantioselectivity. The piperidinols are readily crystallized to obtain enantiopure material.

  DOI：

  10.1021/jo401352z

文献信息

• [EN] METHODS AND COMPOUNDS FOR RESTORING MUTANT p53 FUNCTION<br/>[FR] MÉTHODES ET COMPOSÉS POUR LA RESTAURATION DE LA FONCTION DU P53 MUTANT
  申请人：PMV PHARMACEUTICALS INC

  公开号：WO2021061643A1

  公开（公告）日：2021-04-01

  Mutations in oncogenes and tumor suppressors contribute to the development and progression of cancer. The present disclosure describes compounds and methods to recover wild-type function to p53 mutants. The compounds of the present invention can bind to mutant p53 and restore the ability of the p53 mutant to bind DNA and activate downstream effectors involved in tumor suppression. The disclosed compounds can be used to reduce the progression of cancers that contain a p53 mutation.

  癌基因和肿瘤抑制基因的突变促成了癌症的发展和进展。本公开披露描述了一种恢复p53突变体野生型功能的化合物和方法。本发明的化合物可以结合突变型p53，并恢复p53突变体结合DNA并激活参与肿瘤抑制的下游效应子的能力。所披露的化合物可用于减少含有p53突变的癌症的进展。
• [EN] THIADIAZOLE IRAK4 INHIBITORS<br/>[FR] INHIBITEURS DE THIADIAZOLE IRAK4
  申请人：GILEAD SCIENCES INC

  公开号：WO2020036986A1

  公开（公告）日：2020-02-20

  A compound of Formula (I): (I) pharmaceutically acceptable salts thereof, deuterated analogs thereof, compositions thereof, and methods of treating disease using a compound thereof are disclosed.

  公开了化合物Formula (I)的复合物：(I)的药用盐，其氘代物，其组合物，以及使用其化合物治疗疾病的方法。
• AMPK-activating heterocyclic compounds and methods for using the same
  申请人：Rigel Pharmaceuticals, Inc.

  公开号：US10377742B2

  公开（公告）日：2019-08-13

  Disclosed are substituted pyridine compounds as well as pharmaceutical compositions and methods of use. One embodiment is a compound having the structure wherein E, J, T, the ring system denoted by “B”, T, R3, R4, w and x are as described herein. In certain embodiments, a compound disclosed herein activates the AMPK pathway, and can be used to treat metabolism-related disorders and conditions.

  所公开的是取代的吡啶化合物以及药物组合物和使用方法。其中一种化合物具有如下结构 其中 E、J、T、以 "B "表示的环系、T、R3、R4、w 和 x 如本文所述。在某些实施方案中，本文公开的化合物可激活 AMPK 通路，并可用于治疗与代谢相关的疾病和病症。
• Thiadiazole IRAK4 compounds
  申请人：Gilead Sciences, Inc.

  公开号：US11046686B2

  公开（公告）日：2021-06-29

  A compound of Formula (I): pharmaceutically acceptable salts thereof, deuterated analogs thereof, compositions thereof, and methods of treating disease using a compound thereof are disclosed.

  式 (I) 的化合物： 公开了其药学上可接受的盐、其氚代类似物、其组合物以及使用其化合物治疗疾病的方法。
• Enantioselective Organocatalytic α-Fluorination of Cyclic Ketones
  作者：Piotr Kwiatkowski、Teresa D. Beeson、Jay C. Conrad、David W. C. MacMillan

  DOI：10.1021/ja111163u

  日期：2011.2.16

  The first highly enantioselective alpha-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone alpha-fluorination via enamine activation has been overcome via high-throughput evaluation of a new library of amine catalysts. The optimal system, a primary amine functionalized Cinchona alkaloid, allows the direct and asymmetric a-fluorination of a variety of carbo- and heterocyclic substrates. Furthermore, this protocol also provides diastereo-, regio-, and chemoselective catalyst control in fluorinations involving complex carbonyl systems.