N,N-diethylindoline-1-carboxamide | 61589-12-6

• 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: N,N-diethylindoline-1-carboxamide
• 英文别名: N-(N',N'-diethylcarbamyl)indoline；N,N-diethylcarbamoylindoline；1-(Diethylaminocarbonyl)indoline；N-(Diethylcarbamoyl)-indolin；N-Diethylcarbamoyl-indolin；N,N-diethyl-1-indolinecarboxamide；N,N-diethyl-2,3-dihydroindole-1-carboxamide
• CAS: 61589-12-6
• 化学式: C₁₃H₁₈N₂O
• mdl: MFCD07067418
• 分子量: 218.299
• InChiKey: ZWMBWNRAUWHCID-UHFFFAOYSA-N

物化性质

• 沸点：
  324.1±25.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-diethylindoline-1-carboxamide 在 manganese triacetate 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以82%的产率得到N n-二乙基-1H-吲哚-1-羧酰胺
  参考文献：
  名称：

  The manganese(III) acetate oxidation of N-protected indolines

  摘要：

  DOI：

  10.1016/s0040-4039(00)86696-4
• 作为产物：
  描述：

  (2-(2-(3,3-diethylureido)ethyl)phenyl)(4-fluorophenyl)iodonium p-toluenesulfonate 在 2,2,6,6-四甲基哌啶氧化物 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以70%的产率得到N,N-diethylindoline-1-carboxamide
  参考文献：
  名称：

  Approach to the Synthesis of Indoline Derivatives from Diaryliodonium Salts

  摘要：

  An effective method of constructing the indoline moiety via intramolecular nucleophilic ring closure of a diaryliodonium salt is described. Diacetoxyiodoarene compounds (1a-1e) were converted into intermediate Koser's reagent and coupled with arylstannanes (7-10) to form diaryliodonium salts (11a-14e). Indo line compounds with different N-protecting groups, 15, 16, 17, and 18, were synthesized in higher yields by treating salts (11a-14e) with Cs2CO3 and TEMPO. Regardless of the electronic environment of five para-substituted iodoarenes and the natures of four N-protected arylstannane groups, the conversion proceeded well to afford corresponding indolines in yields of 72-84 and 70-84%, respectively.

  DOI：

  10.1021/jo300874m

文献信息

• Iridium(III)-Catalyzed Direct C-7 Amination of Indolines with Organic Azides
  作者：Kwangmin Shin、Sukbok Chang

  DOI：10.1021/jo5018475

  日期：2014.12.19

  Iridium-catalyzed regioselective C-7 amination of indolines has been achieved with organic azides as a facile nitrogen source. The developed procedure is convenient to perform even at room temperature and applicable to a wide range of substrates with high catalytic activity. Various types of organic azides (sulfonyl, aryl, and alkyl derivatives) were all successfully reacted under the present conditions

  用有机叠氮化物作为方便的氮源，已经完成了铱催化的吲哚的区域选择性C-7胺化反应。所开发的程序即使在室温下也很方便执行，并且适用于具有高催化活性的各种底物。在当前条件下，各种类型的有机叠氮化物（磺酰基，芳基和烷基衍生物）都作为可行的反应物成功地反应了。此外，轴承容易去除二氢吲哚基片Ñ保护基团如ñ -Boc或ñ -Cbz可容易地被采用，突出这种方法的合成的效用。
• Ir(III)-Catalyzed C7-Position-Selective Oxidative CH Alkenylation of Indolines with Alkenes in Air
  作者：Shiguang Pan、Takayuki Wakaki、Naoto Ryu、Takanori Shibata

  DOI：10.1002/asia.201301733

  日期：2014.5

  An efficient method for C7‐position‐selective alkenylation of N‐substituted indolines with alkenes is reported. Various 7‐alkenylindolines were obtained in moderate to excellent yields in air in the presence of catalytic amounts of [Cp*IrCl2]2, AgOTf, and Cu(OAc)2. The protocol relies on the use of a carbonyl or carbamoyl group on the nitrogen atom of indoline as a directing group and is potentially

  报道了一种有效的方法，用于用烯烃对N取代的二氢吲哚进行C7位置选择性烯基化。在催化量的[Cp * IrCl 2 ] 2，AgOTf和Cu（OAc）2的存在下，在空气中以中等至优异的产率获得了各种7-烯基二氢吲哚。该方案依赖于在吲哚啉氮原子上使用羰基或氨基甲酰基作为导向基团，并且可能适用于7-烯基吲哚和7-烷基吲哚的合成。
• Expedient Synthesis of Pyrroloquinolinones by Rh-Catalyzed Annulation of <i>N</i>-Carbamoyl Indolines with Alkynes through a Directed C–H Functionalization/C–N Cleavage Sequence
  作者：Xiao-Fei Yang、Xu-Hong Hu、Teck-Peng Loh

  DOI：10.1021/acs.orglett.5b00355

  日期：2015.3.20

  functionalization of N-carbamoyl indolines with various internal alkynes has been developed. The reaction, which involves the sequential cleavage of the C–H bond of the indoline at the C7-position and the C–N bond of the urea motif, provides a divergent protocol to rapidly assemble fused-ring pyrroloquinolinone analogues by using a direct alkenylation/annulation strategy with high efficiency and selectivity

  已开发了具有各种内部炔烃的Rh催化N-氨基甲酰基二氢吲哚的氧化还原中性C–H功能化。该反应涉及二氢吲哚在C7位的C–H键和尿素基序的C–N键的顺序裂解，提供了通过直接烯基化快速组装稠环吡咯并喹啉酮类似物的协议。 /高效率和选择性的环空策略。
• Rhodium(III)-Catalyzed Direct Regioselective Synthesis of 7-Substituted Indoles
  作者：Zengqiang Song、Rajarshi Samanta、Andrey P. Antonchick

  DOI：10.1021/ol402626t

  日期：2013.11.15

  An efficient, atom-economic one-pot method was developed for the preparation of 7-substituted indoles via rhodium(III)-catalyzed oxidative cross-coupling. Regioselective olefination of indoline derivatives followed by one-pot subsequent oxidation provided the desired products in good to excellent yields.

  开发了一种有效的，原子经济的一锅法，用于通过铑（III）催化的氧化交叉偶联制备7位取代的吲哚。二氢吲哚衍生物的区域选择性烯烃化，然后一锅法随后的氧化，以良好至优异的产率提供了所需的产物。
• 1,3-dihydroindol-2-one derivatives substituted in the 3-position by a
  申请人：Sanofi

  公开号：US05594023A1

  公开（公告）日：1997-01-14

  The present invention relates to compounds of formula (I) and salts thereof, where appropriate: ##STR1## These compounds have an affinity for the vasopressin and/or ocytocin receptors.

  本发明涉及式(I)化合物及其盐，如适用：这些化合物具有对加压素和/或催产素受体的亲和力。