1-Dodecyl-1H-indole-2,3-dione | 201990-39-8

• 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: 1-Dodecyl-1H-indole-2,3-dione
• 英文别名: 1-dodecyl-2,3-dihydro-1H-indole-2,3-dione；1-dodecyl-indoline-2,3-dione；N-dodecanylisatin；1-dodecyl-isatin；N-dodecylisatin；1-Dodecylindoline-2,3-dione；1-dodecylindole-2,3-dione
• CAS: 201990-39-8
• 化学式: C₂₀H₂₉NO₂
• 分子量: 315.456
• InChiKey: GQEQKTGRIPEAKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Dodecyl-1H-indole-2,3-dione 在 六乙基亚磷酸胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Novel isoindigo derivatives bearing long-chain N-alkyl substituents: Synthesis and self-assemble behavior

  摘要：

  A mild, catalyst-free and simple synthesis of 1,1'-di(n-alkyl)-isoindigo via the reaction of substituted isatins with tris(diethylamino) phosphine is reported. Their self-assembly in water-DMF (50% v/v) solution was investigated. Unexpectedly, no surface activity was observed for compound 2h. Spectrophotometry and fluorimetry allowed determining critical micelle concentration (0.1 mM and 0.8 mM respectively). Aggregation numbers of 8 and sizes of aggregates were determined. (C) 2014 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.cplett.2014.01.026
• 作为产物：
  描述：

  1-dodecyl-1H-indole 在 叔丁基过氧化氢 作用下， 以 水 为溶剂， 反应 5.0h， 以82%的产率得到1-Dodecyl-1H-indole-2,3-dione
  参考文献：
  名称：

  TBHP介导的吲哚将底物控制的氧化脱芳香化为C2 / C3-季吲哚啉酮

  摘要：

  据报道，吲哚能有效地进行无金属氧化脱芳香化反应，从而合成各种C2 / C3季吲哚啉酮。吲哚氮原子上取代基的性质决定了反应中形成的产物的类型。

  DOI：

  10.1002/ejoc.201800167

文献信息

• Catalytic asymmetric synthesis of 3-hydroxyl-2-oxindoles via enantioselective Morita–Baylis–Hillman reaction of isatins
  作者：Ci-Ci Wang、Xin-Yan Wu

  DOI：10.1016/j.tet.2011.02.045

  日期：2011.4

  The enantioselective Morita–Baylis–Hillman reaction of acrylates to isatins was investigated for the first time, employing bifunctional phosphinothiourea organocatalysts based on chiral cyclohexane scaffold. The 3-hydroxyl-2-oxindole derivatives were obtained in excellent yields with moderate enantioselectivity (up to 69% ee) in the presence of 10 mol % catalyst 1b.

  首次使用基于手性环己烷骨架的双官能膦硫脲有机催化剂，研究了丙烯酸酯与靛红的对映选择性Morita-Baylis-Hillman反应。在10mol％催化剂1b的存在下，以优异的产率和适度的对映选择性（高达69％ee）获得了3-羟基-2-氧吲哚衍生物。
• Design and synthesis of N-alkyl oxindolylidene acetic acids as a new class of potent Cdc25A inhibitors
  作者：Rumiko Shimazawa、Masami Kuriyama、Ryuichi Shirai

  DOI：10.1016/j.bmcl.2008.04.027

  日期：2008.6

  The oxindolylidene acetic acids having long N-alkyl chains exhibited strong inhibitory activity toward dual specificity phosphatase Cdc25A.

  具有长N-烷基链的二氧杂环丁烯乙酸对双特异性磷酸酶Cdc25A表现出强抑制活性。
• Copper-catalyzed tandem oxidative cyclization of arylacetamides: efficient access to N-functionalized isatins
  作者：Jie Sun、Bingxin Liu、Bin Xu

  DOI：10.1039/c3ra40657a

  日期：——

  An efficient copper-catalyzed synthesis of N-substituted isatins has been developed in good yields from easily accessible arylacetamides. A wide range of electronically and structurally varied nitrogen fragments could be assembled through this tandem C–O/C–N bond-forming process by tuning the reaction conditions.

  已经开发出一种高效的铜催化合成N-取代异烟酸的反应，能够从易于获得的芳基乙酰胺中以良好的产率合成。通过调整反应条件，可以组装多种电子和结构各异的氮基片段，采用这种串联C–O/C–N键形成的过程。
• Driving NHC organocatalysis on water through hydrophobic hydration for the synthesis of diverse heterocycles and carbocycles
  作者：Pavithira Suresh、Subbiah Thamotharan、Subramaniapillai Selva Ganesan

  DOI：10.1016/j.catcom.2018.03.024

  日期：2018.6

  Unprecedented acceleration in the rate of the N-heterocyclic carbene (NHC) organocatalysis was observed while performing the reaction in water medium with NaCl as an additive during the synthesis of diverse spirooxindole-γ-butyrolactone derivatives. The seminal role of hydrophobic hydration effect for the acceleration of the reaction was further proved by performing the reaction with antihydrophobic

  在水介质中与NaCl作为添加剂的合成过程中，在水介质中进行反应时，观察到N杂环卡宾（NHC）有机催化速率的前所未有的加速。通过与抗疏水添加剂LiClO 4进行反应并使用更稠密的D 2 O溶剂进一步证明了疏水水合作用对促进反应的重要作用。
• [EN] HYDRAZONE MODULATORS OF CANNABINOID RECEPTORS<br/>[FR] HYDRAZONES MODULATEURS DE RÉCEPTEURS CANNABINOÏDES
  申请人：UNIV TEXAS

  公开号：WO2009012227A1

  公开（公告）日：2009-01-22

  Hydrazone compounds which modulate cannabinoid receptors are presented. Pharmaceutical compositions containing these compounds, methods of using these compounds as modulators of cannabinoid receptors and processes for synthesizing these compounds are also described herein.

  呈现了调节大麻素受体的腙类化合物。本文还描述了含有这些化合物的药物组合物、使用这些化合物作为大麻素受体调节剂的方法以及合成这些化合物的过程。