2-benzyl-6-formyl-3,4-dihydro-2H-1-benzopyran | 109209-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-benzyl-6-formyl-3,4-dihydro-2H-1-benzopyran
• 英文别名: (R)-(-)-3,4-Dihydro-6-formyl-2-benzyl-2H-benzopyran；2R-benzyl-chroman-6-carbaldehyde；2-benzyl-3,4-dihydro-2H-chromene-6-carbaldehyde
• CAS: 109209-98-5
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: PAFQCPYHHJGCHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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-benzyl-6-formyl-3,4-dihydro-2H-1-benzopyran 在 palladium on activated charcoal 氢气 、 sodium acetate 、 溶剂黄146 作用下， 25.0~140.0 ℃ 、344.73 kPa 条件下， 反应 0.42h， 生成 恩格列酮
  参考文献：
  名称：

  Substituted dihydrobenzopyran and dihydrobenzofuran thiazolidine-2,4-diones as hypoglycemic agents

  摘要：

  A series of dihydrobenzofuran and dihydrobenzopyran thiazolidine-2,4-diones (compounds 3-26) was synthesized from the corresponding aryl aldehydes 1 in two steps. These compounds represent conformationally restricted analogues of the novel hypoglycemic ciglitazone. The series was evaluated by hypoglycemic effects in vitro by measuring stimulation of 2-deoxyglucose uptake in L6 myocytes and stimulation of expression of the glucose transporter protein in 3T3-L1 adipocytes. In vivo hypoglycemic effects were evaluated in the genetically obese ob/ob mouse, and structure-activity relationships are discussed. On the basis of this in vivo potency, we have selected the 2(R)-benzylbenzopyran derivative to be further studied in a clinical setting.

  DOI：

  10.1021/jm00105a050

文献信息

• Process and intermediates for 2R-benzyl-chroman-6-carbaldehyde
  申请人：PFIZER INC.

  公开号：EP0448254A2

  公开（公告）日：1991-09-25

  Optically active (C₁-C₃)alkyl 2R-chroman-2-carboxylates are prepared by partial hydrolysis of the corresponding racemic ester using a microbial lipase as catalyst. Said 2R-chromancarboxylate is converted via novel 2R-(hydroxymethyl)chroman, 2R-(trifluoromethylsulfonyloxymethyl)chroman and 2R-benzylchroman intermediates into 2R-benzylchroman-6-carbaldehyde, a compound of known utility in the manufacture of certain hypoglycemic agents.

  以微生物脂肪酶为催化剂，通过部分水解相应的外消旋酯，制备光学活性（C₁-C₃）烷基 2R-色满-2-羧酸酯。所述 2R-色烷羧酸酯通过新型 2R-(羟甲基)色烷、2R-(三氟甲基磺酰氧甲基)色烷和 2R-苄基色烷中间体转化为 2R-苄基色烷-6-甲醛，这是一种已知可用于制造某些降糖药的化合物。
• J. Med. Chem. 1991, 34, 319-325
  作者：

  DOI：——

  日期：——
• CLARK, DAVID A.;GOLDSTEIN, STEVEN W.;VOLKMANN, ROBERT A.;EGGLER, JAMES F.+, J. MED. CHEM., 34,(1991) N, C. 319-325
  作者：CLARK, DAVID A.、GOLDSTEIN, STEVEN W.、VOLKMANN, ROBERT A.、EGGLER, JAMES F.+

  DOI：——

  日期：——
• Hypoglycemic thiazolidinediones
  申请人：PFIZER INC.

  公开号：EP0207605B1

  公开（公告）日：1990-02-07
• US4703052A
  申请人：——

  公开号：US4703052A

  公开（公告）日：1987-10-27