5,5'-dichloro­-3-­methoxy­-1H,1'H-2,2'­-bisindole | 1422958-00-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5,5'-dichloro­-3-­methoxy­-1H,1'H-2,2'­-bisindole
• 英文别名: 5,5'-dichloro-3-methoxy-1H,1'H-2,2'-bisindole；5,5'-dichloro-3-methoxy-1H,1'H-2,2'-biindole；5-chloro-2-(5-chloro-1H-indol-2-yl)-3-methoxy-1H-indole
• CAS: 1422958-00-6
• 化学式: C₁₇H₁₂Cl₂N₂O
• 分子量: 331.201
• InChiKey: AAVXFXDKGLEUQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,5'-dichloro­-3-­methoxy­-1H,1'H-2,2'­-bisindole 在 乙酸乙酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 2-­(5,5'-­dichloro­‐3'‐methoxy­‐1H,1'H‐2,2'­‐bisindol­‐3‐yl)‐2‐hydroxy-­N1,N3­‐dimethylmalonamide
  参考文献：
  名称：

  Total Synthesis of Cladoniamide G

  摘要：

  The total synthesis of cladoniamide G, a cytotoxic compound against MCF-7 breast cancer cells (10 mu g/mL), was accomplished. Key steps in the sequence include oxidative dimerization of 3-acetoxy-5-chloroindole and a tandem process incorporating three steps: bimolecular carbonyl addition, lactam formation, and carbamate removal.

  DOI：

  10.1021/ol400055v
• 作为产物：
  描述：

  3-乙酰氧基-5-氯吲哚 在 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 20.0h， 生成 5,5'-dichloro­-3-­methoxy­-1H,1'H-2,2'­-bisindole
  参考文献：
  名称：

  Total Synthesis of Cladoniamide G

  摘要：

  The total synthesis of cladoniamide G, a cytotoxic compound against MCF-7 breast cancer cells (10 mu g/mL), was accomplished. Key steps in the sequence include oxidative dimerization of 3-acetoxy-5-chloroindole and a tandem process incorporating three steps: bimolecular carbonyl addition, lactam formation, and carbamate removal.

  DOI：

  10.1021/ol400055v

文献信息

• Unsymmetrical<i>vic</i>-Tricarbonyl Compounds for the Total Syntheses of Cladoniamide G and Cladoniamide F
  作者：Julia Schütte、Frank Kilgenstein、Michel Fischer、Ulrich Koert

  DOI：10.1002/ejoc.201402531

  日期：2014.8

  A 2-unsubstituted indole adds under Cu-box-catalysis to mesoxalic ester amides with high enantioselectivity, whereas low enantiomeric excess is obtained for 2-substituted indoles. A mesoxalic ester amide is used as key component in the total syntheses of alkaloids cladoniamide G and cladoniamide F. The natural product syntheses involve Suzuki cross-coupling to a 2,2′-biindole, arylation of the vic-tricarbonyl

  2-未取代的吲哚在 Cu-box 催化下以高对映选择性加成到间草酸酯酰胺中，而 2-取代的吲哚获得低对映体过量。中草酸酯酰胺用作生物碱克拉多胺 G 和克拉多胺 F 全合成的关键组分。 天然产物合成涉及 Suzuki 与 2,2'-联吲哚的交叉偶联、vic-三羰基化合物的芳基化和分子内内酰胺形成。
• Formal synthesis of (±)-cladoniamide G
  作者：Paiboon Ngernmeesri、Sarochar Soonkit、Anothai Konkhum、Boonsong Kongkathip

  DOI：10.1016/j.tetlet.2014.01.086

  日期：2014.2

  The formal synthesis of (+/-)-cladoniamide G, a natural product that exhibits cytotoxicity against human breast cancer MCF-7 cells, is presented. Our strategy employed a Suzuki-Miyaura coupling to join the two indole subunits of this natural product. (c) 2014 Elsevier Ltd. All rights reserved.
• Total Synthesis of Cladoniamide G
  作者：Benjamin C. Loosley、Raymond J. Andersen、Gregory R. Dake

  DOI：10.1021/ol400055v

  日期：2013.3.1

  The total synthesis of cladoniamide G, a cytotoxic compound against MCF-7 breast cancer cells (10 mu g/mL), was accomplished. Key steps in the sequence include oxidative dimerization of 3-acetoxy-5-chloroindole and a tandem process incorporating three steps: bimolecular carbonyl addition, lactam formation, and carbamate removal.