diethyl (2,3-dihydro-2-oxo-3-indolylidene)propanedioate | 14003-26-0

• 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: diethyl (2,3-dihydro-2-oxo-3-indolylidene)propanedioate
• 英文别名: diethyl 2-(2-oxoindolin-3-ylidene)malonate；2-oxoindolin-3-ylidene diethylmalonate；(2-oxo-indolin-3-ylidene)-malonic acid diethyl ester；(2-Oxo-indolin-3-yliden)-malonsaeure-diaethylester；Isatinyliden-malonsaeure-diethlester；diethyl 2-(2-oxo-1H-indol-3-ylidene)propanedioate
• CAS: 14003-26-0
• 化学式: C₁₅H₁₅NO₅
• 分子量: 289.288
• InChiKey: LBKJPPYCDSYSAC-UHFFFAOYSA-N

物化性质

• 沸点：
  435.7±45.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (2,3-dihydro-2-oxo-3-indolylidene)propanedioate 在 二氢吡啶 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.0h， 以92%的产率得到diethyl 2-(2-oxo-2,3-dihydro-1H-3-indolyl)malonate
  参考文献：
  名称：

  Synthetic and Theoretical Studies on the Reduction of Electron Withdrawing Group Conjugated Olefins Using the Hantzsch 1,4-Dihydropyridine Ester

  摘要：

  The Hantzsch 1,4-dihydropyridine ester (1) has been observed to be a useful selective reducing agent for the reduction of electron-withdrawing conjugated double bonds. The rate of this reaction was observed to be dependent upon the nature of the conjugated substituents and, consequently, the electronic nature of the unsaturated double bond. Theoretical calculations confirmed the importance of the HOMO-LUMO gap for this reaction and implicated a hydride transfer, agreeing with the experimentally observed reaction rate order. The calculations also revealed the importance of a boatlike structure of the 1,4-dihydropyridine nucleus as well as a trans arrangement of the ester groups to facilitate the hydride transfer.

  DOI：

  10.1021/jo034921e
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 aluminum(III) sulfate 、 乙醇 、 硫酸 作用下， 生成 diethyl (2,3-dihydro-2-oxo-3-indolylidene)propanedioate
  参考文献：
  名称：

  Yokoyama, Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1936, vol. 57, p. 251,253

  摘要：

  DOI：

文献信息

• Synthesis and evaluation of oxindoles as promising inhibitors of the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1
  作者：Saurav Paul、Ashalata Roy、Suman Jyoti Deka、Subhankar Panda、Gopal Narayan Srivastava、Vishal Trivedi、Debasis Manna

  DOI：10.1039/c7md00226b

  日期：——

  oxindoles from L-Trp, tryptamine and isatin. Compounds with C3-substituted oxindole moieties showed moderate inhibitory activity against the purified human IDO1 enzyme. Their optimization led to the identification of potent compounds, 6, 22, 23 and 25 (IC50 = 0.19 to 0.62 μM), which are competitive inhibitors of IDO1 with respect to L-Trp. These potent compounds also showed IDO1 inhibition potencies in

  吲哚胺2,3-二加氧酶1（IDO1）被认为是治疗癌症，慢性感染和其他与免疫抑制有关的疾病的重要治疗靶标。在理解IDO1酶的催化机理方面的最新进展表明，L-色氨酸（L- Trp ）向N-甲酰基kynurenine的转化通过环氧化物中间态进行。因此，我们从L -Trp，色胺和靛红合成了一系列3-取代的羟吲哚。具有C3取代的羟吲哚基团的化合物对纯化的人IDO1酶表现出中等的抑制活性。他们的优化导致了鉴定有效的化合物的，6，22，23和25（IC 50 = 0.19至0.62μM），它们是IDO1相对于L -Trp的竞争性抑制剂。这些有效的化合物还在MDA-MB-231细胞中的低微摩尔范围（IC 50 = 0.33–0.49μM）中显示出IDO1抑制能力。这些有效化合物在不同模型的癌细胞（MDA-MB-231，A549和HeLa）和巨噬细胞（J774A.1）中的细胞毒性微不足道。对于这些化合物，还
• Knoevenagel condensation products from some cyclic ketones
  作者：G. Jones、W.J. Rae

  DOI：10.1016/s0040-4020(01)82281-x

  日期：1966.1

  NMR spectra are used to determine the stereochemistry of the Knoevenagel condensation products of type I. Correct structures are given for the products of condensation between ethyl cyanoacetate and isatin, indan-1-one, or indan-2-one; and between α-tetralone and cyano-acetamide.

  NMR光谱用于确定I型Knoevenagel缩合产物的立体化学。给出了氰基乙酸乙酯与靛红，茚满-1-酮或茚满-2-酮之间缩合产物的正确结构；在α-四氢萘酮和氰基乙酰胺之间。
• The diels-alder reaction of isoprene with 2-oxoindolin-3-ylidene derivatives
  作者：C.G. Richards、D.E. Thurston

  DOI：10.1016/s0040-4020(01)88693-2

  日期：1983.1

  The Diels-Alder reaction of isoprene with eight 2-oxoindoline-3-ylidene derivatives is discussed and the structure and conformation of the adducts assigned by the use of 270 MHz PMR spectroscopy. Some transformations of the adducts are also described.

  讨论了异戊二烯与八个2-氧代吲哚啉-3-亚烷基衍生物的Diels-Alder反应，并通过使用270 MHz PMR光谱确定了加合物的结构和构象。还描述了加合物的一些转化。
• Reaction of Isatins with Active Methylene Compounds on Neutral Alumina: Formation of Knoevenagel Condensates and Other Interesting Products
  作者：Manas Chakrabarty、Ratna Mukherjee、Shiho Arima、Yoshihiro Harigaya

  DOI：10.3987/com-08-11504

  日期：——

  and 5-nitro derivatives underwent smooth reaction with a variety of acyclic and cyclic active methylene compounds on neutral alumina at rt to efficiently furnish Knoevenagel condensates in the majority of the cases and tandem Knoevenagel condensation-Michael addition products including spiro compounds in two cases.

  在大多数情况下，靛红及其 N-甲基和 5-硝基衍生物在中性氧化铝上与多种无环和环状活性亚甲基化合物顺利反应，在大多数情况下有效地提供 Knoevenagel 缩合物和串联的 Knoevenagel 缩合-迈克尔加成产物，包括螺环两种情况下的复合。
• TiCl₄/DMAP mediated Z-selective knovenagel condensation of isatins with nitroacetates and related compounds
  作者：Luyi Zhu、Peipei Yan、Lvye Zhang、Zhangtao Chen、Xiaofei Zeng、Guofu Zhong

  DOI：10.1039/c7ra09951g

  日期：——

  A highly efficient Z-selective Knovenagel condensation reaction of isatins with nitroacetates mediated by TiCl4 and DMAP was described. The desired 2-nitro-3-ylideneoxindole acetates were obtained in good to excellent stereoselectivities and yields. Other activated methylene derivatives as well as 4-methylbenzenesulfonamide could provide good results too. This method makes it possible to obtain various

  描述了由TiCl 4和DMAP介导的靛红与硝基乙酸的高效Z选择性Knovenagel缩合反应。以良好至优异的立体选择性和产率获得了所需的2-硝基-3-亚硝基氧吲哚乙酸酯。其他活化的亚甲基衍生物以及4-甲基苯磺酰胺也可以提供良好的结果。该方法可以在温和的反应条件下获得各种未报道的3-亚硝基氧吲哚衍生物。