6-chloro-2-oxo-2H-1-benzopyran-4-yl toluene-4-sulfonate | 345948-97-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-chloro-2-oxo-2H-1-benzopyran-4-yl toluene-4-sulfonate
• 英文别名: 6-chloro-4-tosyloxycoumarin；6-chloro-4-tosylatecoumarin；toluene-4-sulfonic acid 6-chloro-2-oxo-2H-1-benzopyran-4-yl ester；(6-chloro-2-oxochromen-4-yl) 4-methylbenzenesulfonate
• CAS: 345948-97-2
• 化学式: C₁₆H₁₁ClO₅S
• 分子量: 350.779
• InChiKey: CGVYMFAVQXBSCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-chloro-2-oxo-2H-1-benzopyran-4-yl toluene-4-sulfonate 在 二氯双(三邻甲苯膦)合钯(II) 、 氢气 、 镍 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 生成 4-(4-aminobutyl)-6-chloro-1-benzopyran-2-one acetate
  参考文献：
  名称：

  Design, synthesis and characterization of a novel class of coumarin-based inhibitors of inducible nitric oxide synthase

  摘要：

  Inducible nitric oxide synthase (iNOS) has been implicated in various central and peripheral pathophysiological diseases. Our high throughput screening initially identified a weak inhibitor of iNOS, thiocoumarin 13. From this lead, a number of potent derivatives were prepared that demonstrate favorable potency, selectivity and kinetics. Compound 30 has an IC50 of 60 nM for mouse iNOS and 185-fold and 9-fold selectivity for bovine eNOS and rat nNOS, respectively. In cellular assays for iNOS, this compound has micromolar potency. Furthermore, two compounds (16 and 30) demonstrate a reasonable pharmacokinetic profile in rodents. The synthesis, SAR, and biological activity of this novel class of compounds is described.

  DOI：

  10.1016/j.bmc.2005.02.036
• 作为产物：
  描述：

  2-羟基-5-氯苯乙酮 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 6-chloro-2-oxo-2H-1-benzopyran-4-yl toluene-4-sulfonate
  参考文献：
  名称：

  使用二硒化物作为硒源，方便的迈克尔加成/β消除方法合成4-苄基和4-芳基-硒基香豆素

  摘要：

  据报道，从容易获得的4-羟基香豆素中制备4-有机硒烯香豆素衍生物的简洁有效的两步方法。合成基于常规的甲苯磺酸化，然后在相应的4-甲苯磺酰香豆素上进行串联的selena-Michael加成/β-消除芳基-/苄基-硒代硒酸酯阴离子。通过将相应的二硒化物暴露于NaBH 4可以方便地在原位生成硒酸根阴离子。所选化合物在小鼠皮质和海马中表现出抗氧化性能。

  DOI：

  10.1016/j.tetlet.2017.01.084

文献信息

• 4-Thio coumarins
  申请人：——

  公开号：US20040002538A1

  公开（公告）日：2004-01-01

  4-thio substituted coumarin derivatives and coumarin dimers are provided, as well as processes for their preparation. A synthetic process for the preparation of 4-thio substituted coumarin derivatives is provided using mild reaction conditions, which maintains a high substituent tolerance and is appropriate for use in solid phase syntheses for producing a library of 4-thio substituted coumarin derivatives for biological screening.

  提供4-硫代取代香豆素衍生物和香豆素二聚体，以及它们的制备方法。提供了一种使用温和反应条件的合成方法，用于制备4-硫代取代香豆素衍生物，该方法具有高取代基耐受性，并适用于固相合成，以生产用于生物筛选的4-硫代取代香豆素衍生物库。
• Palladium-catalyzed Suzuki–Miyaura couplings of potassium aryl trifluoroborates with 4-tosyloxycoumarins or 4-tosyloxyquinolin-2(1H)-one
  作者：Jie Wu、Liang Zhang、Hong-Guang Xia

  DOI：10.1016/j.tetlet.2006.01.020

  日期：2006.3

  Pd(PPh3)4 catalyzed Suzuki–Miyaura cross-coupling reactions of 4-tosyloxycoumarins or 4-tosyloxyquinolin-2(1H)-one with various potassium aryl trifluoroborates afforded the corresponding 4-substituted coumarins or 4-substituted quinolin-2(1H)-ones in good to excellent yield.

  Pd（PPh 3）4催化4-甲苯磺酰香豆素或4-甲苯磺酰喹啉-2（1 H）-之一与各种芳基三氟硼酸钾盐的Suzuki-Miyaura交叉偶联反应，得到相应的4-取代香豆素或4-取代喹啉-2（ 1 H）-良至优异的收率。
• RhCl(PPh3)3/DPPF: A Useful and Efficient Catalyst for Cross-Coupling Reactions of Activated Alkenyl Tosylates with Arylboronic Acids
  作者：Jie Wu、Liang Zhang、Ke Gao

  DOI：10.1002/ejoc.200600469

  日期：2006.12

  Suzuki–Miyaura cross-coupling of activated alkenyl tosylates is described. The results not only represent the first examples of the rhodium-catalyzed Suzuki–Miyaura coupling of activated alkenyl tosylates with arylboronic acids under mild conditions, but also provide an efficient route for the synthesis of some natural product-like compounds, such as furan-2(5H)-one, coumarin, pyrone, and quinolin-2(1H)-one

  描述了一种有用且有效的铑催化剂体系 - [RhCl(PPh3)3/DPPF] - 用于活化甲苯磺酸烯基酯的 Suzuki-Miyaura 交叉偶联。该结果不仅代表了在温和条件下活化的甲苯磺酸烯基与芳基硼酸在铑催化下 Suzuki-Miyaura 偶联的第一个例子，而且还为合成一些天然产物类化合物（如呋喃-2）提供了有效途径。 (5H)-one、香豆素、吡喃酮和喹啉-2(1H)-one 衍生物。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006）
• Coumarins as iNOS inhibitors
  申请人：Jackson Sharon

  公开号：US20050054681A1

  公开（公告）日：2005-03-10

  The present invention relates to coumarins of the formula (I): that are useful as inhibitors of nitric oxide synthase. Pharmaceutical compositions and methods of using these compounds as inhibitors of nitric oxide synthase are described herein.

  本发明涉及一种具有以下结构的香豆素（I）：这些化合物可作为一氧化氮合酶的抑制剂。本文描述了这些化合物作为一氧化氮合酶抑制剂的药物组合物和使用方法。
• Rh(I)-catalyzed cross-coupling reactions of alkenyl tosylates with potassium aryltrifluoroborates
  作者：Jie Wu、Liang Zhang、Yong Luo

  DOI：10.1016/j.tetlet.2006.07.085

  日期：2006.9

  RhCl(PPh3)3/DPPF was successfully employed as an efficient catalyst in the Suzuki–Miyaura cross-coupling reactions of potassium aryltrifluoroborates with alkenyl tosylates, affording the corresponding products in good to excellent yields.

  RhCl（PPh 3）3 / DPPF已成功地用作芳基三氟硼酸钾与烯基甲苯磺酸盐的Suzuki-Miyaura交叉偶联反应的有效催化剂，以良好的收率获得了相应的产物。