2,2-二甲基-2,3-二氢-1-苯并呋喃-4-甲醛 | 209256-56-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 中文名称: 2,2-二甲基-2,3-二氢-1-苯并呋喃-4-甲醛
• 英文名称: 2,2-dimethyl-2,3-dihydro-benzofuran-4-carboxaldehyde
• 英文别名: 2,2-dimethyl-2,3-dihydro-1-benzofuran-4-carbaldehyde；2,2-dimethyl-3H-1-benzofuran-4-carbaldehyde
• CAS: 209256-56-4
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: LUWDDBYJLRTYOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-二甲基-2,3-二氢-1-苯并呋喃-4-甲醛 、 3-isonicotinoyl-3,9-diazaspiro[5.5]undecane 在 sodium triacetoxyborohydride 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 [9-[(2,2-dimethyl-3H-1-benzofuran-4-yl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-pyridin-4-ylmethanone
  参考文献：
  名称：

  Increasing Selectivity of CC Chemokine Receptor 8 Antagonists by Engineering Nondesolvation Related Interactions with the Intended and Off-Target Binding Sites

  摘要：

  The metabolic stability and selectivity of a series of CCR8 antagonists against binding to the hERG ion channel and cytochrome Cyp2D6 are studied by principal component analysis. It is demonstrated that an efficient way of increasing metabolic stability and selectivity of this series is to decrease compound lipophilicity by engineering nondesolvation related attractive interactions with CCR8, as rationalized by three-dimensional receptor models. Although Such polar interactions led to increased compound selectivity, such a strategy could also jeopardize the DMPK profile of compounds. However, once increased potency is found, the lipophilicity can be readjusted by engineering hydrophobic substituents that fit to CCR8 but do not fit to hERG. Several such lipophilic fragments are identified by two-dimensional fragment-based QSAR analysis. Electrophysiological measurements and site-directed mutagenesis studies indicated that the repulsive interactions of these fragments with hERG are caused by steric hindrances with residue F656.

  DOI：

  10.1021/jm900713y
• 作为产物：
  描述：

  (2,2-dimethyl-2,3-dihydrobenzofuran-4-yI)methanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 氯化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.5h， 以95%的产率得到2,2-二甲基-2,3-二氢-1-苯并呋喃-4-甲醛
  参考文献：
  名称：

  WO2007/30061

  摘要：

  公开号：

文献信息

• [EN] BENZODIOXOLE, BENZOFURAN, DIHYDROBENZOFURAN, AND BENZODIOXANE MELATONERGIC AGENTS<br/>[FR] LES BENZODIOXOLE, BENZOFURAN, DIHYDROBENZOFURAN, ET BENZODIOXANE: DES AGENTS MELATONERGIQUES
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：WO1998025606A1

  公开（公告）日：1998-06-18

  (EN) Novel derivatives of benzodioxole, benzofuran, 2,3-dihydrobenzofuran, and benzodioxane are useful as melatonergic agents.(FR) La présente invention concerne de nouveaux dérivés des benzodioxole, benzofuran, 2,3-dihydrobenzofuran, et benzodioxane qui conviennent particulièrement comme agents mélatonergiques.

  这段话的中文翻译如下： (EN) Novel derivatives of benzodioxole, benzofuran, 2,3-dihydrobenzofuran, and benzodioxane are useful as melatonergic agents. (中) 新型苯并二氧杂环、苯并呋喃、2,3-二氢苯并呋喃和苯并二氧杂环的衍生物可作为褪黑素能药物使用。 (FR) La présente invention concerne de nouveaux dérivés des benzodioxole, benzofuran, 2,3-dihydrobenzofuran, et benzodioxane qui conviennent particulièrement comme agents mélatonergiques. (中) 本发明涉及苯并二氧杂环、苯并呋喃、2,3-二氢苯并呋喃和苯并二氧杂环的新型衍生物，特别适用于作为褪黑素能药物。
• Benzopyran derivatives as melatonergic agents
  申请人：Bristol-Myers Squibb Company

  公开号：US06060506A1

  公开（公告）日：2000-05-09

  Novel derivatives of benzopyran are provided which are useful as melatonergic agents.

  提供了苯并吡喃的新型衍生物，可用作褪黑素受体激动剂。
• Benzofuran and dihydrobenzofuran melatonergic agents
  申请人：Bristol-Myers Squibb Company

  公开号：US05856529A1

  公开（公告）日：1999-01-05

  Novel derivatives of benzofuran and dihydrobenzofuran are provided which are useful as melatonergic agents.

  提供了苯并呋喃和二氢苯并呋喃的新型衍生物，可作为褪黑素受体激动剂。
• Benzodioxa alkylene ethers as melatonergic agents
  申请人：Bristol-Myers Squibb Company

  公开号：US05981571A1

  公开（公告）日：1999-11-09

  Novel derivatives of benzodioxa alkylene ethers are provided which are useful as melatonergic agents.

  提供了苯二氧杂烷醚的新型衍生物，可用作褪黑素受体激动剂。
• ARYLOXYANILIDE IMAGING AGENTS
  申请人：Wadsworth Harry John

  公开号：US20120244073A1

  公开（公告）日：2012-09-27

  The present invention provides a novel radiolabeled aryloxyalinine derivative suitable for in vivo imaging. In comparison to known aryloxyalinine derivative in vivo imaging agents, the in vivo imaging agent of the present invention has better properties for in vivo imaging. The in vivo imaging agent of the present invention demonstrates good selective binding to the peripheral benzodiazepine receptor (PBR), in combination with good brain uptake and in vivo kinetics following administration to a subject.

  本发明提供了一种新型放射性标记的芳氧基丙氨酸衍生物，适用于体内成像。与已知的芳氧基丙氨酸衍生物体内成像剂相比，本发明的体内成像剂具有更好的体内成像性能。本发明的体内成像剂在给予受试者后，表现出良好的选择性结合到周边苯二氮平受体（PBR），并具有良好的脑摄取和体内动力学。