3-(3’,4’-methylenedioxy-6’-nitro)phenylpropan-1-ol | 189813-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-(3’,4’-methylenedioxy-6’-nitro)phenylpropan-1-ol
• 英文别名: 3-(3',4'-methylenedioxy-6'-nitro)phenyl propan-1-ol；3-(6-nitrobenzo[1,3]dioxol-5-yl)propan-1-ol；3-(6-Nitro-1,3-benzodioxol-5-yl)propan-1-ol
• CAS: 189813-94-3
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: ZPORPASSBNRQGW-UHFFFAOYSA-N

物化性质

• 熔点：
  85.9-87.9 °C
• 沸点：
  383.4±42.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3’,4’-methylenedioxy-6’-nitro)phenylpropan-1-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 3-[(3,4-methylenedioxy)-6-amino]phenyl-1-propanol
  参考文献：
  名称：

  Structure−Activity Relationships of N ²-Aryl-3-(isoxazolylsulfamoyl)-2-thiophenecarboxamides as Selective Endothelin Receptor-A Antagonists

  摘要：

  We report here that N-2-aryl-3-(isoxazolylsulfamoyl)-2-thiophenecarboxamides are potent and selective small molecule ETA receptor antagonists. The aryl group was subjected to extensive structural modification. With monosubstitution, the para position was most useful in increasing potency, with methyl being preferred. With disubstitution, 2,4-disubstitution further enhanced activity with methyl or cyano groups being preferred at the 2-position. In this series, a benzo-[d][1,3]dioxole group is equivalent to a 4-methyl group in in vitro activity and afforded the compounds with both in vivo activity and moderate half-lives.

  DOI：

  10.1021/jm9608366
• 作为产物：
  描述：

  3-[3,4-(亚甲二氧基)苯基]丙酸 在 硼烷四氢呋喃络合物 、 硝酸 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 3-(3’,4’-methylenedioxy-6’-nitro)phenylpropan-1-ol
  参考文献：
  名称：

  Structure−Activity Relationships of N ²-Aryl-3-(isoxazolylsulfamoyl)-2-thiophenecarboxamides as Selective Endothelin Receptor-A Antagonists

  摘要：

  We report here that N-2-aryl-3-(isoxazolylsulfamoyl)-2-thiophenecarboxamides are potent and selective small molecule ETA receptor antagonists. The aryl group was subjected to extensive structural modification. With monosubstitution, the para position was most useful in increasing potency, with methyl being preferred. With disubstitution, 2,4-disubstitution further enhanced activity with methyl or cyano groups being preferred at the 2-position. In this series, a benzo-[d][1,3]dioxole group is equivalent to a 4-methyl group in in vitro activity and afforded the compounds with both in vivo activity and moderate half-lives.

  DOI：

  10.1021/jm9608366

文献信息

• [EN] A PROCESS FOR SYNTHESIS OF CHIRAL 3-SUBSTITUTED TETRAHYDROQUINOLINE DERIVATIVES<br/>[FR] PROCESSUS DE SYNTHÈSE DE DÉRIVÉS TÉTRAHYDROQUINOLINE CHIRAUX 3-SUBSTITUÉS
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2013140419A1

  公开（公告）日：2013-09-26

  The present invention relates to novel and concise process for the construction of chiral 3-substituted tetrahydroquinoline derivatives based on proline catalyzed asymmetric α-functionalization of aldehyde, followed by in situ reductive cyclization of nitro group under catalytic hydrogenation condition with high optical purities. Further the invention relates to conversion of derived chiral 3-substituted tetrahydroquinoline derivatives into therapeutic agents namely (-)-sumanirole (96% ee) and 1-[(S)-3-(dimethylamino)-3,4-dihydro-6,7-dimethoxy-quinolin-1(2H)-yl]propanone[(S)-903] (92% ee).

  本发明涉及一种新颖简洁的过程，用于构建基于脯氨酸催化的不对称α-醛功能化的手性3-取代四氢喹啉衍生物，随后在高光学纯度下在催化氢化条件下进行硝基基团的原位还原环化。此外，该发明涉及将衍生的手性3-取代四氢喹啉衍生物转化为治疗剂，即(-)-苏马尼罗尔（96% ee）和1-[(S)-3-(二甲基氨基)-3,4-二產-6,7-二甲氧基喹啉-1(2H)-基]丙酮[(S)-903]（92% ee）。
• Catalan, Luis Espinoza; Villegas, Alejandro Madrid; Liber, Lautaro Taborga, Journal of the Chilean Chemical Society, 2010, vol. 55, # 2, p. 219 - 222
  作者：Catalan, Luis Espinoza、Villegas, Alejandro Madrid、Liber, Lautaro Taborga、Garcia, Joan Villena、Fritis, Mauricio Cuellar、Altamirano, Hector Carrasco

  DOI：——

  日期：——
• Structure−Activity Relationships of <i>N</i> ²-Aryl-3-(isoxazolylsulfamoyl)-2-thiophenecarboxamides as Selective Endothelin Receptor-A Antagonists
  作者：Chengde Wu、Ming F. Chan、Fiona Stavros、B. Raju、Ilya Okun、Rosario S. Castillo

  DOI：10.1021/jm9608366

  日期：1997.5.1

  We report here that N-2-aryl-3-(isoxazolylsulfamoyl)-2-thiophenecarboxamides are potent and selective small molecule ETA receptor antagonists. The aryl group was subjected to extensive structural modification. With monosubstitution, the para position was most useful in increasing potency, with methyl being preferred. With disubstitution, 2,4-disubstitution further enhanced activity with methyl or cyano groups being preferred at the 2-position. In this series, a benzo-[d][1,3]dioxole group is equivalent to a 4-methyl group in in vitro activity and afforded the compounds with both in vivo activity and moderate half-lives.