1-Benzyl-isatin-3-yliden-cyanessigsaeure-ethylester | 26960-51-0

• 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: 1-Benzyl-isatin-3-yliden-cyanessigsaeure-ethylester
• 英文别名: ethyl (E)-2-(1-benzyl-2-oxoindolin-3-ylidene)-2-cyanoacetate；(E)-Cyano(1-benzyl-2-oxoindoline-3-ylidene)acetic acid ethyl ester；ethyl (2E)-2-(1-benzyl-2-oxoindol-3-ylidene)-2-cyanoacetate
• CAS: 26960-51-0
• 化学式: C₂₀H₁₆N₂O₃
• 分子量: 332.359
• InChiKey: ILSBZJQRTQRMSR-FBMGVBCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  1-Benzyl-isatin-3-yliden-cyanessigsaeure-ethylester 、 3-丁炔-2-酮 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以93%的产率得到ethyl 3-acetyl-9-benzyl-4-cyano-4,9-dihydropyrano[2,3-b]indole-4-carboxylate
  参考文献：
  名称：

  Phosphorus-containing Lewis base catalyzed highly regioselective cyclization of isatin derived electron-deficient alkenes with but-3-yn-2-one

  摘要：

  In this paper, we reported that phosphorus-containing Lewis bases catalyzed [4+2] cyclization of N-protected isatin derived electron-deficient alkenes with but-3-yn-2-one could proceed smoothly to give the corresponding dihydropyrano[2,3-b]indoles in good to excellent yields under mild conditions. The substrate scope has been carefully examined and the plausible reaction mechanism has been also proposed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.036
• 作为产物：
  描述：

  靛红 在 哌啶 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-Benzyl-isatin-3-yliden-cyanessigsaeure-ethylester
  参考文献：
  名称：

  Phosphorus-containing Lewis base catalyzed highly regioselective cyclization of isatin derived electron-deficient alkenes with but-3-yn-2-one

  摘要：

  In this paper, we reported that phosphorus-containing Lewis bases catalyzed [4+2] cyclization of N-protected isatin derived electron-deficient alkenes with but-3-yn-2-one could proceed smoothly to give the corresponding dihydropyrano[2,3-b]indoles in good to excellent yields under mild conditions. The substrate scope has been carefully examined and the plausible reaction mechanism has been also proposed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.036

文献信息

• Iron-catalyzed cross-dehydrogenative coupling of indolin-2-ones with active methylenes for direct carbon–carbon double bond formation
  作者：Zhi-Yu Tan、Ke-Xin Wu、Lu-Shan Huang、Run-Shi Wu、Zheng-Yu Du、Da-Zhen Xu

  DOI：10.1039/c9gc03639c

  日期：——

  The iron-catalyzed cross-dehydrogenative coupling (CDC) of C(sp3)–H/C(sp3)–H bonds to afford olefins by 4H elimination is described. This method employs air (molecular oxygen) as an ideal oxidant, and is performed under mild, ligand-free and base-free conditions. H2O is the only byproduct. Good tolerance of functional groups and high yields have also been achieved. Preliminary mechanistic investigations

  描述了铁催化的C（sp 3）–H / C（sp 3）–H键的交叉脱氢偶联（CDC），可通过4H消除得到烯烃。该方法使用空气（分子氧）作为理想的氧化剂，并且在温和，无配体和无碱的条件下进行。H 2 O是唯一的副产物。还获得了对官能团的良好耐受性和高产率。初步的机械研究表明，目前的转变涉及一个根本过程。
• Organocatalytic Enantioselective Synthesis of Polysubstituted Spirooxindoles using a Tandem Michael-Michael Reaction
  作者：Santhi Abbaraju、Naresh Ramireddy、Nirmal K. Rana、Hadi Arman、John C.-G. Zhao

  DOI：10.1002/adsc.201500298

  日期：2015.8.24

  A highly efficient stereoselective method for the synthesis of functionalized spirooxindole derivatives with four contiguous stereogenic centers, including two adjacent quaternary stereogenic centers, was realized through an organocatalytic tandem Michael–Michael reaction. By employing a quinidine‐derived thiourea organocatalyst, the reaction between (E)‐2‐cyano‐2‐(2‐oxo‐1‐tritylindolin‐3‐ylidene)acetates

  通过有机催化串联迈克尔-迈克尔反应实现了一种高效的立体选择性方法，该方法用于合成具有四个连续的立体中心（包括两个相邻的季立体中心）的功能化螺恶灵吲哚衍生物。通过使用奎尼丁衍生的硫脲有机催化剂，（E）-2-氰基-2-（2-氧代-1-三苯并噻唑啉-3-亚基）乙酸酯与（E）-1-烷基-6-硝基己基之间的反应‐‐2 ‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐__________________®的螺恶诺吲哚产物具有良好的收率（高达90％）和良好的立体选择性（高达95：5 dr和98％ee）。