4-(1,3-Benzodioxol-5-yl)-6-methyl-3,4-dihydrochromen-2-one | 1071613-68-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 4-(1,3-Benzodioxol-5-yl)-6-methyl-3,4-dihydrochromen-2-one
• CAS: 1071613-68-7
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: ZZHUIWAIHYIBCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二甲基哌啶 、 4-(1,3-Benzodioxol-5-yl)-6-methyl-3,4-dihydrochromen-2-one 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-(1,3-Benzodioxol-5-yl)-1-(3,5-dimethylpiperidin-1-yl)-3-(2-hydroxy-5-methylphenyl)propan-1-one
  参考文献：
  名称：

  Small molecule amides as potent ROR-γ selective modulators

  摘要：

  The structure-activity relationship study of a diphenylpropanamide series of ROR-gamma selective modulators is reported. Compounds were screened using chimeric receptor Gal4 DNA-binding domain (DBD)-NR ligand binding domain cotransfection assay in a two-step format. Three different regions of the scaffold were modified to assess the effects on repression of ROR-gamma transcriptional activity and potency. The lead compound 1 exhibits modest mouse pharmacokinetics and an acceptable in vitro profile which makes it a suitable in vivo probe to interrogate the functions of ROR-gamma in animal models of disease. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.025
• 作为产物：
  描述：

  对甲酚 、 3,4-(亚甲二氧)肉桂酸 在 三氟乙酸 作用下， 反应 0.5h， 生成 4-(1,3-Benzodioxol-5-yl)-6-methyl-3,4-dihydrochromen-2-one
  参考文献：
  名称：

  Small molecule amides as potent ROR-γ selective modulators

  摘要：

  The structure-activity relationship study of a diphenylpropanamide series of ROR-gamma selective modulators is reported. Compounds were screened using chimeric receptor Gal4 DNA-binding domain (DBD)-NR ligand binding domain cotransfection assay in a two-step format. Three different regions of the scaffold were modified to assess the effects on repression of ROR-gamma transcriptional activity and potency. The lead compound 1 exhibits modest mouse pharmacokinetics and an acceptable in vitro profile which makes it a suitable in vivo probe to interrogate the functions of ROR-gamma in animal models of disease. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.025

文献信息

• Stepwise Palladium-Catalyzed 1,4-Addition of Arylboronic Acids to Enones and Regioselective Baeyer–Villiger Oxidation for Enantioselective Synthesis of β-Diaryl Esters and (+)-(<i>R</i>)-Tolterodine
  作者：Kenya Kobayashi、Takashi Nishikata、Yasunori Yamamoto、Norio Miyaura

  DOI：10.1246/bcsj.81.1019

  日期：2008.8.15

  Baeyer-Villiger oxidation of chiral β-diaryl ketones synthesized by 1,4-addition of arylboronic acids to β-aryl-α,β-unsaturated ketones catalyzed by a palladium(2+)-chiraphos complex provided optically active /3-diaryl esters up to 98% ee. The protocol was applied to the synthesis of a potent competitive muscarinic receptor antagonist, (R)-tolterodine (21), which has a chiral center consisting of two

  Baeyer-Villiger 氧化手性 β-二芳基酮，由芳基硼酸 1,4-加成到 β-芳基-α，β-不饱和酮，由钯（2+）-手性磷配合物催化，提供旋光/3-二芳基酯高达 98% ee。该方案用于合成有效的竞争性毒蕈碱受体拮抗剂 (R)-托特罗定 (21)，其具有由两个芳环组成的手性中心。