2-bromo-5-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine | 214119-24-1

• 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: 2-bromo-5-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine
• 英文别名: N,N'-Dibenzenesulfonyl-5-bromo-2-methoxy-1,4-phenylenediamine；N-[4-(benzenesulfonamido)-2-bromo-5-methoxyphenyl]benzenesulfonamide
• CAS: 214119-24-1
• 化学式: C₁₉H₁₇BrN₂O₅S₂
• 分子量: 497.39
• InChiKey: NHXQMRLHHGNBSV-UHFFFAOYSA-N

物化性质

• 熔点：
  224 °C(Solv: acetic acid (64-19-7))
• 沸点：
  624.1±65.0 °C(Predicted)
• 密度：
  1.615±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-bromo-5-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine 在 zirconocene methyl chloride 、 水 、 碘 、 叔丁基锂 、 silica gel 、 四丁基碘化铵 、 sodium hydride 、 silver(l) oxide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 110.0h， 生成 N-Allyl-N-(1-benzenesulfonyl-3-hydroxymethyl-4-iodo-6-methoxy-2,3-dihydro-1H-indol-5-yl)-benzenesulfonamide
  参考文献：
  名称：

  Efficient Synthesis of the Pharmacophore of the Highly Potent Antitumor Antibiotic CC-1065

  摘要：

  The pharmacophore CPI (3) of the potent antitumor antibiotic CC-1065 (1) was synthesized in a very short reaction sequence of 11 steps with an overall yield of 23 %. The key steps are two consecutive cyclizations mediated by organotransition metal complexes, which form first the pyrroline and then the pyrrole ring in 3. Thus, halogen metal exchange of the N,N'-bisallylbromobenzene with rBuLi and subsequent reaction with Cp2ZrMeCl gave 11 as a single product in 60 % yield after quenching with two equivalents of iodine. Transformation of the iodomethyl group in 11 into an acetoxymethyl group, followed by Heck reaction, isomerization, and reductive cleavage, provided the pyrroloindoline system 4, which was converted into 3.

  DOI：

  10.1002/(sici)1521-3765(19980807)4:8<1554::aid-chem1554>3.0.co;2-j
• 作为产物：
  描述：

  1,4-二氨基-2-甲氧基苯 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 2-bromo-5-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine
  参考文献：
  名称：

  通过两个连续的过渡金属引发的转化合成抗肿瘤抗生素 CC-1065 的环尺寸 seco-类似物

  摘要：

  CC-1065 1 的新型 seco-analogs 是由市售的硝基苯胺通过还原、溴化、双磺化和双烯丙基化，然后与叔丁基锂、二茂锆和碘反应合成的。然后将获得的喹啉 6 转化为 17 和 18，在用 Pd0 处理后，分别产生 21 和 22。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200300077

文献信息

• Efficient Synthesis of the Pharmacophore of the Highly Potent Antitumor Antibiotic CC-1065
  作者：Lutz F. Tietze、Wilm Buhr、Jan Looft、Thomas Grote

  DOI：10.1002/(sici)1521-3765(19980807)4:8<1554::aid-chem1554>3.0.co;2-j

  日期：1998.8.7

  The pharmacophore CPI (3) of the potent antitumor antibiotic CC-1065 (1) was synthesized in a very short reaction sequence of 11 steps with an overall yield of 23 %. The key steps are two consecutive cyclizations mediated by organotransition metal complexes, which form first the pyrroline and then the pyrrole ring in 3. Thus, halogen metal exchange of the N,N'-bisallylbromobenzene with rBuLi and subsequent reaction with Cp2ZrMeCl gave 11 as a single product in 60 % yield after quenching with two equivalents of iodine. Transformation of the iodomethyl group in 11 into an acetoxymethyl group, followed by Heck reaction, isomerization, and reductive cleavage, provided the pyrroloindoline system 4, which was converted into 3.
• Synthesis of Ring Size seco-Analogs of the Antitumor Antibiotic CC-1065 by Two Consecutive Transition Metal-Initiated Transformations
  作者：Lutz F. Tietze、Jan Looft、Tim Feuerstein

  DOI：10.1002/ejoc.200300077

  日期：2003.8

  Novel seco-analogs of CC-1065 1 were synthesized from comercially available nitroaniline by reduction, bromination, bisulfonation and bisallylation followed by reaction with tert-butyllithium, zirconocene and iodine. The obtained quinoline 6 was then transformed into 17 and 18, which, upon treatment with Pd0, led to 21 and 22, respectively. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany

  CC-1065 1 的新型 seco-analogs 是由市售的硝基苯胺通过还原、溴化、双磺化和双烯丙基化，然后与叔丁基锂、二茂锆和碘反应合成的。然后将获得的喹啉 6 转化为 17 和 18，在用 Pd0 处理后，分别产生 21 和 22。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)