2,2-Dimethylbenzo[d][1,3]dioxole-4-carbaldehyde | 134817-17-7

• 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: 2,2-Dimethylbenzo[d][1,3]dioxole-4-carbaldehyde
• 英文别名: 2,2-dimethyl-1,3-benzodioxole-4-carbaldehyde
• CAS: 134817-17-7
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: RMOKRPOMUJFXSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2,2-Dimethylbenzo[d][1,3]dioxole-4-carbaldehyde 以81%的产率得到
  参考文献：
  名称：

  Huang Ded-Shih, Ting Su-Hwa, J. Chem. Res. Synop, (1994) N 12, S 500-501

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2-二甲基-1,3-苯并二恶茂烷 、 N,N-二甲基甲酰胺 在 正丁基锂 作用下， 生成 2,2-Dimethylbenzo[d][1,3]dioxole-4-carbaldehyde
  参考文献：
  名称：

  Preparation of chiral cyanohydrins by an oxynitrilase-mediated transcyanation

  摘要：

  The transcyanation of aromatic and aliphatic aldehydes 1 (RCHO) with acetone cyanohydrin is catalyzed by the enzyme D-oxynitrilase to afford (R)-cyanohydrins 2 (RCH(OH)CN). The biocatalytic method using acetone cyanohydrin gives products of high enantiomeric purity with better consistency than similar conditions using hydrogen cyanide as the cyanide source. The use of an ether-buffer biphasic solvent system is essential for producing products of optimum optical purity, but the solubility properties of the substrate have a pronounced effect on the enantiomeric purity of the final product. A discussion relating the solubility partition coefficient (log P) of a substrate to the enantiomeric purity of the product as a guide for predicting the outcome with new substrates is presented. Application of the method to the preparation of the following cyanohydrins is reported (R, ee): a, C6H5, 92% ee; b, 3,4-(CH2O2)C6H3, 90% ee; c, 2-(CH3O)C6H4, 96% ee; d, C6H5CH2, 88% ee; e, CH3SCH2CH2, 92% ee; f, CH3(CH2)5CH2, 92% ee; g, (CH3)3C, 92% ee; h, c-C6H11, 96% ee; i, CH3O2C(CH2)6CH2, 97% ee; j, (E,E)-CH3CH = CHCH = CH, 96% ee; k, (CH3)2C = CHCH2CH2C(CH3) = CH, 99% ee.

  DOI：

  10.1021/ja00018a042

文献信息

• NOVEL DIAZASPIROALKANES AND THEIR USE FOR TREATMENT OF CCR8 MEDIATED DISEASES
  申请人：Borjesson Lena

  公开号：US20090156575A1

  公开（公告）日：2009-06-18

  The invention provides compounds of general formula wherein A, B, p, w, x, y, and z are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了一般式为的化合物，其中A、B、p、w、x、y和z的定义如规范中所述，以及其制备方法、包含它们的药物组合物和它们在治疗中的应用。
• Increasing Selectivity of CC Chemokine Receptor 8 Antagonists by Engineering Nondesolvation Related Interactions with the Intended and Off-Target Binding Sites
  作者：Igor Shamovsky、Chris de Graaf、Lisa Alderin、Malena Bengtsson、Håkan Bladh、Lena Börjesson、Stephen Connolly、Hazel J. Dyke、Marco van den Heuvel、Henrik Johansson、Bo-Göran Josefsson、Anna Kristoffersson、Tero Linnanen、Annea Lisius、Roope Männikkö、Bo Nordén、Steve Price、Lena Ripa、Didier Rognan、Alexander Rosendahl、Marco Skrinjar、Klaus Urbahns

  DOI：10.1021/jm900713y

  日期：2009.12.10

  The metabolic stability and selectivity of a series of CCR8 antagonists against binding to the hERG ion channel and cytochrome Cyp2D6 are studied by principal component analysis. It is demonstrated that an efficient way of increasing metabolic stability and selectivity of this series is to decrease compound lipophilicity by engineering nondesolvation related attractive interactions with CCR8, as rationalized by three-dimensional receptor models. Although Such polar interactions led to increased compound selectivity, such a strategy could also jeopardize the DMPK profile of compounds. However, once increased potency is found, the lipophilicity can be readjusted by engineering hydrophobic substituents that fit to CCR8 but do not fit to hERG. Several such lipophilic fragments are identified by two-dimensional fragment-based QSAR analysis. Electrophysiological measurements and site-directed mutagenesis studies indicated that the repulsive interactions of these fragments with hERG are caused by steric hindrances with residue F656.
• DING, Y. -S.;SHIUE, C. -Y.;FOWLER, J. S.;WOLF, A. P.;PLENEVAUX, A., J. FLUOR. CHEM., 48,(1990) N, C. 189-206
  作者：DING, Y. -S.、SHIUE, C. -Y.、FOWLER, J. S.、WOLF, A. P.、PLENEVAUX, A.

  DOI：——

  日期：——
• Huang Ded-Shih, Ting Su-Hwa, J. Chem. Res. Synop, (1994) N 12, S 500-501
  作者：Huang Ded-Shih, Ting Su-Hwa

  DOI：——

  日期：——
• US5840997A
  申请人：——

  公开号：US5840997A

  公开（公告）日：1998-11-24