2-[(4-phenylmethoxyphenyl)methyl]-3,4-dihydro-2H-chromene-6-carbaldehyde | 120355-99-9

• 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-[(4-phenylmethoxyphenyl)methyl]-3,4-dihydro-2H-chromene-6-carbaldehyde
• CAS: 120355-99-9
• 化学式: C₂₄H₂₂O₃
• 分子量: 358.437
• InChiKey: CZSPPHQNTCYKIC-UHFFFAOYSA-N

物化性质

• 熔点：
  162-163 °C
• 沸点：
  541.2±38.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(4-phenylmethoxyphenyl)methyl]-3,4-dihydro-2H-chromene-6-carbaldehyde 在 palladium on activated charcoal 氢溴酸 、 氢气 、 sodium acetate 、 溶剂黄146 作用下， 25.0~140.0 ℃ 、344.73 kPa 条件下， 反应 1.92h， 生成 5-<(2-(4-hydroxybenzyl)-3,4-dihydro-2H-1-benzopyran-6-yl)methyl>thiazolidine-2,4-dione
  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
• 作为产物：
  描述：

  6-bromo-2-[(4-phenylmethoxyphenyl)methyl]-3,4-dihydro-2H-chromene 生成 2-[(4-phenylmethoxyphenyl)methyl]-3,4-dihydro-2H-chromene-6-carbaldehyde
  参考文献：
  名称：

  CLARK, DAVID A.

  摘要：

  DOI：

文献信息

• CLARK, DAVID A.
  作者：CLARK, DAVID A.

  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：——
• 3-ARYL-2-HYDROXYPROPIONIC ACID DERIVATIVES AND ANALOGS AS HYPOGLYCEMIC AGENTS
  申请人：PFIZER INC.

  公开号：EP0533781A1

  公开（公告）日：1993-03-31
• US5089514A
  申请人：——

  公开号：US5089514A

  公开（公告）日：1992-02-18
• US5232945A
  申请人：——

  公开号：US5232945A

  公开（公告）日：1993-08-03