N-[1-(benzenesulfonyl)-4-iodo-3-(iodomethyl)-6-methoxy-2,3-dihydroindol-5-yl]-N-prop-2-enylbenzenesulfonamide | 165817-07-2

• 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: N-[1-(benzenesulfonyl)-4-iodo-3-(iodomethyl)-6-methoxy-2,3-dihydroindol-5-yl]-N-prop-2-enylbenzenesulfonamide
• CAS: 165817-07-2
• 化学式: C₂₅H₂₄I₂N₂O₅S₂
• 分子量: 750.417
• InChiKey: QVGZGMFEEKHOMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[1-(benzenesulfonyl)-4-iodo-3-(iodomethyl)-6-methoxy-2,3-dihydroindol-5-yl]-N-prop-2-enylbenzenesulfonamide 在 silver(II) oxide 、 kieselgel 、 水 作用下， 以 丙酮 为溶剂， 反应 24.0h， 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：

  Tietze, Lutz F.; Buhr, Wilm, Angewandte Chemie, 1995, vol. 107, # 12, p. 1485 - 1487

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲氧基-4-硝基-6-溴苯胺 在 吡啶 、 zirconocene methyl chloride 、 碘 、 叔丁基锂 、 三氯化铁 、 四丁基碘化铵 、 sodium hydride 、 甲烷 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 67.0h， 生成 N-[1-(benzenesulfonyl)-4-iodo-3-(iodomethyl)-6-methoxy-2,3-dihydroindol-5-yl]-N-prop-2-enylbenzenesulfonamide
  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

文献信息

• Tietze, Lutz F.; Buhr, Wilm, Angewandte Chemie, 1995, vol. 107, # 12, p. 1485 - 1487
  作者：Tietze, Lutz F.、Buhr, Wilm

  DOI：——

  日期：——
• 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.