6-chloro-3-oxo-2-phenyl-3H-indole 1-oxide | 74625-87-9

• 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: 6-chloro-3-oxo-2-phenyl-3H-indole 1-oxide
• 英文别名: 6-Chloro-1-oxy-2-phenyl-indol-3-one；3H-Indol-3-one, 6-chloro-2-phenyl-, 1-oxide；6-chloro-1-oxido-2-phenylindol-1-ium-3-one
• CAS: 74625-87-9
• 化学式: C₁₄H₈ClNO₂
• 分子量: 257.676
• InChiKey: YYPUVYPFZAUPRW-UHFFFAOYSA-N

物化性质

• 熔点：
  162 °C
• 沸点：
  466.2±47.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-十二烯十二碳烯α-十二碳烯α-十二碳烯 、 6-chloro-3-oxo-2-phenyl-3H-indole 1-oxide 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 1-金刚烷甲酸 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以71%的产率得到6-chloro-2-(2-oxododecyl)-2-phenylindolin-3-one
  参考文献：
  名称：

  Ru-Catalyzed Redox-Neutral Cleavage of the N–O Bond in Isoxazolidines: Isatogens to Pseudoindoxyls via a One-Pot [3 + 2]-Cycloaddition/N–O Cleavage

  摘要：

  A novel metal-catalyzed oxygen atom transfer reaction onto olefins is reported. By taking isatogens as substrates, a one-pot [3 + 2]-cycloaddition of nitrone with olefins followed by the Ru-catalyzed redox-neutral N-O bond cleavage of intermediate isoxazolidine has been executed as a simple method for the synthesis of 2,2-disubstituted pseudoindoxyls.

  DOI：

  10.1021/acs.orglett.5b00837
• 作为产物：
  描述：

  1-(4-氯-2-硝基苯)乙酮 在 三氟化硼乙醚 、 双氧水 、 sodium acetate 、 potassium carbonate 作用下， 以 乙醇 、 水 、 苯 为溶剂， 生成 6-chloro-3-oxo-2-phenyl-3H-indole 1-oxide
  参考文献：
  名称：

  Sahasrabudhe, A. B.; Kamath, H. V.; Bapat, B. V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 3, p. 230 - 232

  摘要：

  DOI：

文献信息

• Catalytic asymmetric formal [3+2] cycloaddition of isatogens with azlactones to construct indolin-3-one derivatives
  作者：Lihua Xie、Yi Li、Shunxi Dong、Xiaoming Feng、Xiaohua Liu

  DOI：10.1039/d0cc06418a

  日期：——

  A number of enantioenriched indolin-3-one derivatives were readily obtained by chiral guanidine-catalyzed [3+2] cycloaddition of isatogens with azlactones.

  一些手性瓜尼丁催化的异丙基吲哚啉-3-酮衍生物通过异丙基吲哚啉与氮丙烯酮的手性[3+2]环加成反应轻松获得。
• One-Pot Au[III]-/Lewis Acid Catalyzed Cycloisomerization of Nitroalkynes and [3 + 3]Cycloaddition with Donor–Acceptor Cyclopropanes
  作者：Pawan S. Dhote、Chepuri V. Ramana

  DOI：10.1021/acs.orglett.9b02035

  日期：2019.8.16

  tricyclic pseudoindoxyl scaffold from 2-nitroalkynylbenzenes, comprising of an Au(III)-catalyzed nitroalkyne cycloisomerization leading to isatogen and its [3 + 3]-cycloaddition with donor–acceptor cyclopropanes mediated by a suitable Lewis acid, has been developed.

  一锅法从2-硝基炔基苯合成三环假吲哚基骨架的方案，包括Au（III）催化的硝基炔基环异构化反应，导致异构体及其与供体-受体环丙烷的[3 + 3]-环加成反应。路易斯酸，已经开发出来。
• InCl3-Mediated Addition of Indole to Isatogens: An Expeditious Synthesis of 13-deoxy-Isatisine A
  作者：Chepuri V. Suneel Kumar、Vedavati G Puranik、Chepuri V. Ramana

  DOI：10.1002/chem.201103604

  日期：2012.7.27

  has been developed. As a part of this strategy, methods for the addition of indoles to isatogens that lead selectively to either 2,2‐disubstituted N‐hydroxyindolin‐3‐one or 2,2‐disubstituted indolin‐3‐one compounds have been developed by employing InCl3 as a catalyst or as the reagent. The present methods provide the first examples of the additions of indoles to the isatogen nucleus. To demonstrate

  已经开发出了一种针对板蓝根A的全合成的策略，该策略涉及几个后期的金属催化转化，以解决关键的碳-碳和碳-碳杂原子键形成问题。作为该策略的一部分，通过使用InCl，已经开发了将吲哚添加到致突变剂中的方法，这些方法可选择性地导致2,2-二取代的N-羟基吲哚-3-酮或2,2-二取代的吲哚-3-酮化合物。3作为催化剂或试剂。本发明的方法提供了将吲哚添加到致病原核中的第一个例子。为了证明其可行性，已经从已知且易于获得的内酯通过十步完成了13-脱氧-伊司替丁A的合成。
• Rh(III)-Catalyzed C7-Alkylation of Isatogens with Malonic Acid Diazoesters
  作者：Xiang Guan、Wen-Jie Li、Ming-Shan Shuai、Mao Zhang、Chao-Chao Zhou、Xiao-Zhong Fu、Yuan-Yong Yang、Meng Zhou、Bin He、Yong-Long Zhao

  DOI：10.1021/acs.joc.3c02405

  日期：2024.3.1

  Rh(III)-catalyzed C7-alkylation of isatogens (indolin-3-one N-oxides) with malonic acid diazoesters has been developed. This strategy utilizes oxygen anion on the N-oxide group of isatogens as a directing group and successfully achieves the synthesis of a series of C7-alkylated isatogens with moderate to good yields (48–86% yields). Moreover, the N-oxides of isatogens can not only serve as the simple

  已经开发出 Rh(III) 催化的靛红素（二氢吲哚-3-酮N-氧化物）与丙二酸重氮酯的 C7 烷基化反应。该策略利用靛蓝蛋白N-氧化物基团上的氧阴离子作为导向基团，成功合成了一系列C7-烷基化靛蓝蛋白，收率中等至良好（48-86%）。此外，异酪素的N-氧化物不仅可以作为C7-H键断裂的简单导向基团，而且可以脱氧以便于去除。
• AuBr3-catalyzed cyclization of o-(alkynyl)nitrobenzenes. Efficient synthesis of isatogens and anthranils
  作者：Naoki Asao、Kenichiro Sato、Yoshinori Yamamoto

  DOI：10.1016/s0040-4039(03)01357-1

  日期：2003.7

  The cyclization of o-(arylalkynyl)nitrobenzenes was catalyzed by AuBr3 to produce the corresponding isatogens in good to high yields together with small amounts of anthranils. On the other hand, anthranils were obtained selectively when the AuBr3-catalyzed reaction was carried out using o-(alkylalkynyl)nitrobenzenes. (C) 2003 Elsevier Ltd. All rights reserved.