5-bromo-4-methyl-3-ethyl-2-tosyl-pyrrole | 250380-42-8

• 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: 5-bromo-4-methyl-3-ethyl-2-tosyl-pyrrole
• 英文别名: 2-bromo-4-ethyl-3-methyl-5-(4-methylphenyl)sulfonyl-1H-pyrrole
• CAS: 250380-42-8
• 化学式: C₁₄H₁₆BrNO₂S
• 分子量: 342.257
• InChiKey: KRCGWTCNNVUHQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-4-methyl-3-ethyl-2-tosyl-pyrrole 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 4-乙基-3-甲基-3-吡咯啉-2-酮
  参考文献：
  名称：

  以 2-甲苯磺酰基-3,4-二取代吡咯为原料，方便且区域选择性地合成 3,4-二取代 Δ3-Pyrrolin-2-one 衍生物

  摘要：

  通过 5-tosyl-Δ3-pyrrolin-2-ones (4) 从 2-tosylpyrroles 开始区域选择性地制备 3,4-二取代的 Δ3-pyrrolin-2-ones。发现化合物4是用于制备多种Δ3-吡咯啉-2-酮衍生物的有用中间体。描述了 4 与各种亲核试剂和带有适当离去基团的活性亚甲基化合物的反应。

  DOI：

  10.1246/cl.1993.1437
• 作为产物：
  描述：

  2-硝基戊烷-3-醇 在 4-二甲氨基吡啶 、 溴 、 四甲基胍 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 为溶剂， 反应 70.17h， 生成 5-bromo-4-methyl-3-ethyl-2-tosyl-pyrrole
  参考文献：
  名称：

  Synthesis of a 10-Oxo-Bilirubin:  Effects of the Oxo Group on Conformation, Transhepatic Transport, and Glucuronidation

  摘要：

  Bilirubin, the yellow pigment of jaundice, is a linear tetrapyrrole with a methylene group at its center, C(10), a position of crucial importance to its conformation and metabolism. The presence of the central methylene group allows the bilirubin to fold into an intramolecularly hydrogen-bonded conformation. This paper describes the first synthesis of a bilirubin analogue with an oxo group at C(10). The change from CH2 to C=O, from sp(3) to sp(2), is designed to stress the molecule at its hinge and relax its conformation. Such compounds have been suggested as potential oxidative metabolites of bilirubin in vivo. 10-Oxo-mesobilirubin-XIII alpha (1) is a red crystalline solid, unlike its parent, mesobilirubin-XIII alpha, which is a bright yellow solid. It is surprisingly polar, relative to the parent, yet it does not exhibit a significantly larger bicarbonate/chloroform partition coefficient. Like the parent, 1 appears to adopt an intramolecularly hydrogen-bonded ridge-tile-like conformation. In normal rats, 1 is metabolized to acylglucuronides, which are secreted into bile, but a portion of the administered dose is secreted into bile intact. In mutant rats (Gunn rats) lacking bilirubin glucuronyl transferase, 1 was excreted efficiently in bile in unchanged form, unlike the parent with a methylene group at C(10). Thus, introduction of the oxygen function at C(10) has little effect on hepatic uptake but a dramatic effect on canalicular secretion into bile.

  DOI：

  10.1021/ja991814m

文献信息

• Convenient and Regioselective Syntheses of 3,4-Disubstituted Δ³-Pyrrolin-2-one Derivatives Starting from 2-Tosyl-3,4-Disubstituted Pyrroles
  作者：Hideki Kinoshita、Yoshio Hayashi、Yasue Murata、Katsuhiko Inomata

  DOI：10.1246/cl.1993.1437

  日期：1993.8

  3,4-Disubstituted Δ3-pyrrolin-2-ones were prepared in high yields via 5-tosyl-Δ3-pyrrolin-2-ones (4) starting from 2-tosylpyrroles regioselectively. The compounds 4 were found to be useful intermediates for the preparation of a variety of Δ3-pyrrolin-2-one derivatives. The reactions of 4 with various nucleophiles and active methylene compounds bearing an appropriate leaving group are described.

  通过 5-tosyl-Δ3-pyrrolin-2-ones (4) 从 2-tosylpyrroles 开始区域选择性地制备 3,4-二取代的 Δ3-pyrrolin-2-ones。发现化合物4是用于制备多种Δ3-吡咯啉-2-酮衍生物的有用中间体。描述了 4 与各种亲核试剂和带有适当离去基团的活性亚甲基化合物的反应。
• Synthesis of a 10-Oxo-Bilirubin:  Effects of the Oxo Group on Conformation, Transhepatic Transport, and Glucuronidation
  作者：Qingqi Chen、Michael T. Huggins、David A. Lightner、Wilma Norona、Antony F. McDonagh

  DOI：10.1021/ja991814m

  日期：1999.10.1

  Bilirubin, the yellow pigment of jaundice, is a linear tetrapyrrole with a methylene group at its center, C(10), a position of crucial importance to its conformation and metabolism. The presence of the central methylene group allows the bilirubin to fold into an intramolecularly hydrogen-bonded conformation. This paper describes the first synthesis of a bilirubin analogue with an oxo group at C(10). The change from CH2 to C=O, from sp(3) to sp(2), is designed to stress the molecule at its hinge and relax its conformation. Such compounds have been suggested as potential oxidative metabolites of bilirubin in vivo. 10-Oxo-mesobilirubin-XIII alpha (1) is a red crystalline solid, unlike its parent, mesobilirubin-XIII alpha, which is a bright yellow solid. It is surprisingly polar, relative to the parent, yet it does not exhibit a significantly larger bicarbonate/chloroform partition coefficient. Like the parent, 1 appears to adopt an intramolecularly hydrogen-bonded ridge-tile-like conformation. In normal rats, 1 is metabolized to acylglucuronides, which are secreted into bile, but a portion of the administered dose is secreted into bile intact. In mutant rats (Gunn rats) lacking bilirubin glucuronyl transferase, 1 was excreted efficiently in bile in unchanged form, unlike the parent with a methylene group at C(10). Thus, introduction of the oxygen function at C(10) has little effect on hepatic uptake but a dramatic effect on canalicular secretion into bile.