(3RS)-3-(Acetoxymethyl)-5-(acetylamino)-1-(benzenesulfonyl)-6-(benzyloxy)-4-iodo-2,3-dihydro-1H-indole | 153914-86-4

• 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)-3-(Acetoxymethyl)-5-(acetylamino)-1-(benzenesulfonyl)-6-(benzyloxy)-4-iodo-2,3-dihydro-1H-indole
• 英文别名: [5-Acetamido-1-(benzenesulfonyl)-4-iodo-6-phenylmethoxy-2,3-dihydroindol-3-yl]methyl acetate
• CAS: 153914-86-4
• 化学式: C₂₆H₂₅IN₂O₆S
• 分子量: 620.465
• InChiKey: WBLGGRMEAAEXMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3RS)-3-(Acetoxymethyl)-5-(acetylamino)-1-(benzenesulfonyl)-6-(benzyloxy)-4-iodo-2,3-dihydro-1H-indole 在 palladium diacetate 氢氧化钾 、 camphor-10-sulfonic acid 、 四丁基氯化铵 、 sodium acetate 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.75h， 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 、 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 77.25h， 生成 (3RS)-3-(Acetoxymethyl)-5-(acetylamino)-1-(benzenesulfonyl)-6-(benzyloxy)-4-iodo-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.