5-tosyloxy-pentanal-dimethylacetal | 23068-89-5

• 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: 5-tosyloxy-pentanal-dimethylacetal
• 英文别名: 5,5-dimethoxypentyl 4-methylbenzenesulfonate；5,5-Dimethoxy-1-pentyl-tosylat；5,5-Dimethoxypentyl 4-methylbenzenesulfonate
• CAS: 23068-89-5
• 化学式: C₁₄H₂₂O₅S
• 分子量: 302.392
• InChiKey: ZOUGWFXYAUYIFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  20.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-tosyloxy-pentanal-dimethylacetal 在 正丁基锂 、 lithium bromide 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 、 丙酮 为溶剂， 反应 16.5h， 生成 7-Phenyl-6-heptynal dimethyl acetal
  参考文献：
  名称：

  Domino imine condensation/intramolecular polar [4?+ + 2?]-cycloaddition of anilines and ?-unsaturated aldehydes: A versatile tool for the highly diastereoselective synthesis of 1,2,3,4,4a,9,9a,10-octahydroacridines

  摘要：

  The highly diastereoselective synthesis of substituted 1,2,3,4,4a,9,9a,10-octahydroacridines 7, 8 with five stereogenic centers has been achieved by domino imine condensation/intramolecular polar [4 pi(+)+2 pi]-cycloaddition of anilines 3 and omega-unsaturated aldehydes 4. The transformations which can be performed under mild reaction conditions using 0.3 eq. BF3 . Et(2)O as a Lewis acid give the cycloadducts 7, 8 with yields ranging from 63-76%. The relative configuration of 7, 8 was assigned by H-1- and C-13-NMR spectroscopy. For 7a, an X-ray crystal structure analysis was obtained. Experimental as well as semiempirical results support a polar [4 pi(+) + 2 pi]-cycloaddition under kinetic control. It is assumed that the diastereoselectivity of the process is governed by decalin-like exo-E-anti-transition state structures 24, 25 with equatorial arrangement of the bulky substituents R(2).

  DOI：

  10.1002/prac.19963380189
• 作为产物：
  描述：

  5,5-二甲氧基戊酸甲酯 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 20.0h， 生成 5-tosyloxy-pentanal-dimethylacetal
  参考文献：
  名称：

  Domino imine condensation/intramolecular polar [4?+ + 2?]-cycloaddition of anilines and ?-unsaturated aldehydes: A versatile tool for the highly diastereoselective synthesis of 1,2,3,4,4a,9,9a,10-octahydroacridines

  摘要：

  The highly diastereoselective synthesis of substituted 1,2,3,4,4a,9,9a,10-octahydroacridines 7, 8 with five stereogenic centers has been achieved by domino imine condensation/intramolecular polar [4 pi(+)+2 pi]-cycloaddition of anilines 3 and omega-unsaturated aldehydes 4. The transformations which can be performed under mild reaction conditions using 0.3 eq. BF3 . Et(2)O as a Lewis acid give the cycloadducts 7, 8 with yields ranging from 63-76%. The relative configuration of 7, 8 was assigned by H-1- and C-13-NMR spectroscopy. For 7a, an X-ray crystal structure analysis was obtained. Experimental as well as semiempirical results support a polar [4 pi(+) + 2 pi]-cycloaddition under kinetic control. It is assumed that the diastereoselectivity of the process is governed by decalin-like exo-E-anti-transition state structures 24, 25 with equatorial arrangement of the bulky substituents R(2).

  DOI：

  10.1002/prac.19963380189

文献信息

• [EN] ANDROGEN RECEPTOR MODULATORS AND METHODS FOR USE AS BIFUNCTIONAL DEGRADERS<br/>[FR] MODULATEURS DE RÉCEPTEURS DES ANDROGÈNES ET PROCÉDÉS D'UTILISATION EN TANT QU'AGENTS DE DÉGRADATION BIFONCTIONNELS
  申请人：[en]ESSA PHARMA, INC.

  公开号：WO2023056423A1

  公开（公告）日：2023-04-06

  The present invention relates to bifunctional chemical protein degraders comprising a ligase modulator/binder and a molecule that binds to a protein target of interest, and methods of treating various diseases and conditions with the degrader compounds, including diseases associated with androgen receptors.