2-(甲硫基)-3-硝基苯甲醛 | 106500-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(甲硫基)-3-硝基苯甲醛
• 英文名称: 2-(methylthio)-3-nitrobenzaldehyde
• 英文别名: 2-Methylsulfanyl-3-nitrobenzaldehyde
• CAS: 106500-59-8
• 化学式: C₈H₇NO₃S
• 分子量: 197.214
• InChiKey: DXWSVWLXHNGXPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(甲硫基)-3-硝基苯甲醛 生成 2,6-Dimethyl-4-(2-methylsulfanyl-3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  BALDWIN J. J.; CLAREMON D. A.; LUMMA P. K.; MCCLURE D. E.; ROSENTHAL S. A+, J. MED. CHEM., 30,(1987) N 4, 690-695

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-3-硝基苯甲酸甲酯 在 manganese(IV) oxide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 76.5h， 生成 2-(甲硫基)-3-硝基苯甲醛
  参考文献：
  名称：

  Diethyl 3,6-dihydro-2,4-dimethyl-2,6-methano-1,3-benzothiazocine-5,11-dicarboxylates as calcium entry antagonists: new conformationally restrained analogs of Hantzsch 1,4-dihydropyridines related to nitrendipine as probes for receptor-site conformation

  摘要：

  The pharmacological activity of rigid analogues of 1,4-dihydropyridine calcium entry antagonists 9-16 is demonstrated by dose-dependent inhibition of the calcium contraction in depolarized rat aortic strips and by a [3H]nitrendipine binding assay in using cardiac sarcolemmal membranes. From the results, a model is proposed as the receptor-bound conformation of the dihydropyridine calcium entry antagonists.

  DOI：

  10.1021/jm00387a019

文献信息

• Method for producing 1,2-benzisothiazol-3-ones
  申请人：SUMITOMO SEIKA CHEMICALS CO., LTD.

  公开号：EP0702008A2

  公开（公告）日：1996-03-20

  A method for producing a 1,2-benzisothiazol-3-one, having the steps of carrying out a reaction of a 2-(alkylthio)benzaldehyde with a hydroxylamine to give a 2-(alkylthio)benzaldehyde oxime and carrying out a reaction of the 2-(alkylthio)benzaldehyde oxime with a halogenating agent; and a method for producing a 1,2-benzisothiazol-3-one, having the steps of carrying out a reaction of a 2-halobenzonitrile with an alkanethiol in a heterogeneous solvent system in the presence of a base to give a 2-(alkylthio)benzonitrile and carrying out a reaction of the 2-(alkylthio)benzonitrile with an halogenating agent in the presence of water.

  一种生产 1,2-苯并异噻唑-3-酮的方法，包括以下步骤：将 2-(烷硫基)苯甲醛与羟胺反应生成 2-(烷硫基)苯甲醛肟，并将 2-(烷硫基)苯甲醛肟与卤化剂反应；以及一种生产 1,2-苯并异噻唑-3-酮的方法，其步骤包括：在异相溶剂体系中，在碱存在下，使 2-卤代苯腈与烷硫醇反应，得到 2-(烷基硫基)苯腈；在水存在下，使 2-(烷基硫基)苯腈与卤化剂反应。
• Calcium Entry Blockers and Activators: Conformational and Structural Determinants of Dihydropyrimidine Calcium Channel Modulators
  作者：George C. Rovnyak、S. David Kimball、Barbara Beyer、Gabriella Cucinotta、John D. DiMarco、Jack Gougoutas、Anders Hedberg、Mary Malley、James P. McCarthy

  DOI：10.1021/jm00001a017

  日期：1995.1

  Dihydropyrimidines 4, 6, and 15, uniquely designed to unambiguously establish structural and conformational determinants for DHP receptor occupation and for modulation of calcium channel function, were prepared and examined for calcium channel modulation. Our results confirm and firmly establish a preference for syn-orientation of an unsymmetrically substituted aryl moiety at the DHP receptor (15d vs 15e). We propose a normal vs capsized DHP boat model to explain structural and conformational requirements for modulation of calcium channel function that requires an obligatory left-hand side alkoxy cis-carbonyl interaction for maximal DHP receptor affinity, the effect on channel function being determined by orientation of the 4-aryl group. Enantiomers having an up-oriented pseudoaxial aryl group (normal DHP boat) will elicit calcium antagonist activity, whereas enantiomers having a down-oriented pseudoaxial aryl group (capsized DHP boat) will elicit calcium agonist activity. Single enantiomers of macrocyclic lactone 15b demonstrate opposite channel activity. Antagonist activity resides in enantiomer 15b-A (S-configuration, left-hand side alkoxy cis-carbonyl with up-oriented pseudoaxial aryl group and normal DHP boat), whereas agonist activity resides in enantiomer 15b-B (R-configuration, left-hand side alkoxy cis-carbonyl with down-oriented pseudoaxial aryl group and capsized DHP boat). Moreover, this model is consistent with and provides a rational explanation of previous literature in this area, most notably the observation of chiral inversion and potency diminution upon replacement of ester by hydrogen in the Bay K 8644 series.
• BALDWIN J. J.; CLAREMON D. A.; LUMMA P. K.; MCCLURE D. E.; ROSENTHAL S. A+, J. MED. CHEM., 30,(1987) N 4, 690-695
  作者：BALDWIN J. J.、 CLAREMON D. A.、 LUMMA P. K.、 MCCLURE D. E.、 ROSENTHAL S. A+

  DOI：——

  日期：——
• US5633384A
  申请人：——

  公开号：US5633384A

  公开（公告）日：1997-05-27
• US5773626A
  申请人：——

  公开号：US5773626A

  公开（公告）日：1998-06-30