toluene-4-sulfonic acid 6-methyl-pyridin-3-yl ester | 74838-56-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: toluene-4-sulfonic acid 6-methyl-pyridin-3-yl ester
• 英文别名: 6-Methylpyridin-3-yl 4-methylbenzene-1-sulfonate；(6-methylpyridin-3-yl) 4-methylbenzenesulfonate
• CAS: 74838-56-5
• 化学式: C₁₃H₁₃NO₃S
• 分子量: 263.317
• InChiKey: UTWUXTMFSCYGRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  toluene-4-sulfonic acid 6-methyl-pyridin-3-yl ester 在 盐酸 、 manganese(IV) oxide 、 sodium tetrahydroborate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 108.5h， 生成 1-<<5-<(p-tolylsulfonyl)oxy>-2-pyridyl>methyl>imidazole-2-thione hydrochloride
  参考文献：
  名称：

  Inhibitors of dopamine .beta.-hydroxylase. 3. Some 1-(pyridylmethyl)imidazole-2-thiones

  摘要：

  The 1-benzylimidazole-2-thione moiety has been previously shown by Kruse et al. to be broadly associated with dopamine beta-hydroxylase (DBH) inhibitory activity both in vitro and in vivo in spontaneously hypertensive rats (SHR). An extension of structure-activity studies to 1-(pyridylmethyl)- and 1-(oxypyridylmethyl)imidazole-2-thiones is reported here in an attempt to exploit the pH differential that exists across the chromaffin vesicle membrane. We hypothesized that the weakly basic pyridyl compounds would diffuse into the acidic vesicles in their neutral forms where protonation and concentration would occur to enhance their in vivo effectiveness as inhibitors. To test this hypothesis, isomeric 2-, 3- and 4-(1-pyridylmethyl)imidazole-2-thiones were synthesized from the appropriate pyridinecarboxaldehydes by reductive alkylation of aminoacetaldehyde dialkyl acetal followed by imidazole-2-thione formation using acidic potassium thiocyanate. Related oxypyridyl compounds were synthesized by first preparing the appropriate aldehyde intermediate followed by conversion to the imidazole-2-thione by the same procedure. The unsubstituted pyridylmethyl compounds showed modest DBH inhibition in vitro but, consistent with a transport-mediated increase in observed potency, showed significant effects in vivo to increase the vascular ratio of dopamine to norepinephrine and to lower blood pressure.

  DOI：

  10.1021/jm00391a008
• 作为产物：
  描述：

  3-羟基-6-甲基吡啶 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到toluene-4-sulfonic acid 6-methyl-pyridin-3-yl ester
  参考文献：
  名称：

  苄基锌试剂与芳族溴化物，氯化物和甲苯磺酸盐的镍催化交叉偶联反应。

  摘要：

  通过在LiCl的存在下将锌直接插入苄基氯中而制备的苄锌试剂，使用Ni（acac）（2）和PPh（3）作为催化剂体系，与芳香族氯化物，溴化物和甲苯磺酸盐进行平滑的交叉偶联反应。

  DOI：

  10.1039/b803072c

文献信息

• Nickel-catalyzed cross-coupling reactions of benzylic zinc reagents with aromatic bromides, chlorides and tosylates
  作者：Matthias A. Schade、Albrecht Metzger、Stephan Hug、Paul Knochel

  DOI：10.1039/b803072c

  日期：——

  Benzylic zinc reagents prepared by direct insertion of zinc to benzylic chlorides in the presence of LiCl undergo smooth cross-coupling reactions with aromatic chlorides, bromides and tosylates using Ni(acac)(2) and PPh(3) as a catalyst system.

  通过在LiCl的存在下将锌直接插入苄基氯中而制备的苄锌试剂，使用Ni（acac）（2）和PPh（3）作为催化剂体系，与芳香族氯化物，溴化物和甲苯磺酸盐进行平滑的交叉偶联反应。
• THIAZOLIDINE CARBOXAMIDE DERIVATIVES AS MODULATORS OF THE PROSTAGLANDIN F RECEPTOR
  申请人：PAGE Patrick Naxos

  公开号：US20080255094A1

  公开（公告）日：2008-10-16

  The present invention is related to thiazolidine carboxamide derivatives of formula (II) for the treatment and/or prophylaxis of preterm labor, premature birth, dysmenorrhea and for stopping labor prior to cesarean delivery.

  本发明涉及式（II）的噻唑烷羧酰胺衍生物，用于治疗和/或预防早产、早产、痛经以及在剖腹产前停止分娩。
• Dopamine-beta-hydroxylase inhibitors
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0214740A2

  公开（公告）日：1987-03-18

  Compounds of structure (I) in which Y is H, OH, halogen or C1-4 alkoxy; X is H, halogen, halo C1-4 alkyl, n is 1 to 5 and R is H or C1-4 alkyl and phar- maceu- tically acceptable salts or hydrates thereof, processes fortheir preparation, compositions containing them and their use in therapy.

  结构(I)的化合物 其中 Y 为 H、OH、卤素或 C1-4 烷氧基；X 为 H、卤素、卤代 C1-4 烷基，n 为 1 至 5，R 为 H 或 C1-4 烷基，以及它们的可接受盐或水合物。 及其可接受的盐或水合物、其制备工艺、含有它们的组合物以及它们在治疗中的用途。
• ROSS, S. T.;KRUSE, L. I.;OHLSTEIN, E. H.;ERICKSON, R. W.;EZEKIEL, M.;FLAI+, J. MED. CHEM., 30,(1987) N 8, 1309-1313
  作者：ROSS, S. T.、KRUSE, L. I.、OHLSTEIN, E. H.、ERICKSON, R. W.、EZEKIEL, M.、FLAI+

  DOI：——

  日期：——
• KAISER, CARL;KRUSE, LAWRENCE;ROSS, STEPHEN T.
  作者：KAISER, CARL、KRUSE, LAWRENCE、ROSS, STEPHEN T.

  DOI：——

  日期：——