(3RS)-1-(Benzenesulfonyl)-6-(benzyloxy)-4-iodo-3-(iodomethyl)-2,3-dihydro-1H-indole | 153914-81-9

• 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: (3RS)-1-(Benzenesulfonyl)-6-(benzyloxy)-4-iodo-3-(iodomethyl)-2,3-dihydro-1H-indole
• 英文别名: 1-(Benzenesulfonyl)-4-iodo-3-(iodomethyl)-6-phenylmethoxy-2,3-dihydroindole
• CAS: 153914-81-9
• 化学式: C₂₂H₁₉I₂NO₃S
• 分子量: 631.273
• InChiKey: MFGYJOUIJDQOHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3RS)-1-(Benzenesulfonyl)-6-(benzyloxy)-4-iodo-3-(iodomethyl)-2,3-dihydro-1H-indole 在 palladium diacetate 吡啶 、 氢氧化钾 、 camphor-10-sulfonic acid 、 四丁基氯化铵 、 硝酸 、 sodium acetate 、 三氯化铁 、 sodium hydride 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 硝基甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.25h， 生成 5-(benzyloxy)-1,2-dihydro-1-(hydroxymethyl)-8-methyl-3-(phenylsulfonyl)-3H-pyrrolo<3,2-e>indole
  参考文献：
  名称：

  Synthesis of (.+-.)-N2-(benzenesulfonyl)-CPI, the protected A-unit of the antitumor antibiotic CC-1065, by two metal-initiated cyclizations

  摘要：

  A new synthetic route to (+/-)-N-2-(Benzenesulfonyl)-CPI (16), the protected A-unit containing a cyclopropylhexadienone moiety of the highly potent antitumor antibiotic CC-1065 (1), from 5-(benzyloxy)-2-bromophenylamine (3) is described. The key steps are a zirconium- and a palladium-initiated cyclization to give the two pyrrole moieties. Reaction of 4a with zirconocene (methyl) chloride leads after workup with I-2 to the 4-iodoindoline 7a, which was transformed into 12 and subsequently via Heck reaction into the pyrroloindoline 15.

  DOI：

  10.1021/jo00080a031
• 作为产物：
  描述：

  5-苄氧基-２-溴苯胺 在 吡啶 、 zirconocene methyl chloride 、 碘 、 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.75h， 生成 (3RS)-1-(Benzenesulfonyl)-6-(benzyloxy)-4-iodo-3-(iodomethyl)-2,3-dihydro-1H-indole
  参考文献：
  名称：

  Synthesis of (.+-.)-N2-(benzenesulfonyl)-CPI, the protected A-unit of the antitumor antibiotic CC-1065, by two metal-initiated cyclizations

  摘要：

  A new synthetic route to (+/-)-N-2-(Benzenesulfonyl)-CPI (16), the protected A-unit containing a cyclopropylhexadienone moiety of the highly potent antitumor antibiotic CC-1065 (1), from 5-(benzyloxy)-2-bromophenylamine (3) is described. The key steps are a zirconium- and a palladium-initiated cyclization to give the two pyrrole moieties. Reaction of 4a with zirconocene (methyl) chloride leads after workup with I-2 to the 4-iodoindoline 7a, which was transformed into 12 and subsequently via Heck reaction into the pyrroloindoline 15.

  DOI：

  10.1021/jo00080a031

文献信息

• Synthesis of (.+-.)-N2-(benzenesulfonyl)-CPI, the protected A-unit of the antitumor antibiotic CC-1065, by two metal-initiated cyclizations
  作者：Lutz F. Tietze、Thomas Grote

  DOI：10.1021/jo00080a031

  日期：1994.1

  A new synthetic route to (+/-)-N-2-(Benzenesulfonyl)-CPI (16), the protected A-unit containing a cyclopropylhexadienone moiety of the highly potent antitumor antibiotic CC-1065 (1), from 5-(benzyloxy)-2-bromophenylamine (3) is described. The key steps are a zirconium- and a palladium-initiated cyclization to give the two pyrrole moieties. Reaction of 4a with zirconocene (methyl) chloride leads after workup with I-2 to the 4-iodoindoline 7a, which was transformed into 12 and subsequently via Heck reaction into the pyrroloindoline 15.