Indol-2(3H)-one, 3,2'-spiro(5,5-dimethyl-1,3-dioxane)- | 362000-60-0

• 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: Indol-2(3H)-one, 3,2'-spiro(5,5-dimethyl-1,3-dioxane)-
• 英文别名: 5,5-dimethylspiro[1,3-dioxane-2,3'-1H-indole]-2'-one
• CAS: 362000-60-0
• 化学式: C₁₃H₁₅NO₃
• mdl: MFCD02648697
• 分子量: 233.267
• InChiKey: JOPZGFLVJQSJLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Indol-2(3H)-one, 3,2'-spiro(5,5-dimethyl-1,3-dioxane)- 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以60%的产率得到5',5'-dimethylspiro[indoline-3,2'-[1,3]dioxane]-2-thione
  参考文献：
  名称：

  硫辛醇和芳烃的化学选择性芳基化反应合成2-（芳硫基）吲哚胺

  摘要：

  化学选择性S-硫代羟吲哚与arynes的芳基化反应被呈现。该反应在温和的条件下进行，可直接合成2-（芳硫基）吲哚胺，收率良好。此外，这种简单的操作协议不仅可扩展，而且具有良好的功能组兼容性和基板范围。因此，我们的方案应允许通过开发硫代亚氨酸酯的新支架来扩展化学空间，而这些支架否则很难合成。

  DOI：

  10.1002/adsc.202000308
• 作为产物：
  描述：

  靛红 、 2,2-二甲基-1,3-丙二醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 Indol-2(3H)-one, 3,2'-spiro(5,5-dimethyl-1,3-dioxane)-
  参考文献：
  名称：

  Exploring unsymmetrical dyads as efficient inhibitors against the insect β-N-acetyl-d-hexosaminidase OfHex2

  摘要：

  The GH20 beta-N-acetyl-D-hexosaminidase OfHex2 from the insect Ostrinia furnacalis (Guenee) is a target potential for eco-friendly pesticide development. Although carbohydrate-based inhibitors against beta-Nacetyl-D-hexosaminidases are widely studied, highly efficient, non-carbohydrate inhibitors are more attractive due to low cost and readily synthetic manner. Based on molecular modeling analysis of the catalytic domain of OfHex2, a series of novel naphthalimide-scaffold conjugated with a small aromatic moiety by an alkylamine spacer linker were designed and evaluated as efficiently competitive inhibitors against OfHex2. The most potent one containing naphthalimide and phenyl groups spanning by an N-alkylamine linker has a K-i value of 0.37 mu M, which is 6 fold lower than that of M-31850, the most potent non-carbohydrate inhibitor ever reported. The straightforward synthetic manners as well as the presumed binding model in this paper could be advantageous for further structural optimization for developing inhibitors against GH20 beta-N-acetyl-D-hexosaminidases. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2013.10.008

文献信息

• Synthesis of 2‐(Arylthio)indolenines via Chemoselective Arylation of Thio‐Oxindoles with Arynes
  作者：Adi Saputra、Rong Fan、Tuanli Yao、Jian Chen、Jiajing Tan

  DOI：10.1002/adsc.202000308

  日期：2020.7.16

  A chemoselective S‐ arylation reaction of thio‐oxindoles with arynes is presented. The reaction was performed under mild conditions and provided a straightforward synthesis of 2‐(arylthio)indolenines in good to excellent yields. Besides, this simple operational protocol is not only scalable but also has good functional group compatibilities and substrate scope. Thus, our protocol should allow for the

  化学选择性S-硫代羟吲哚与arynes的芳基化反应被呈现。该反应在温和的条件下进行，可直接合成2-（芳硫基）吲哚胺，收率良好。此外，这种简单的操作协议不仅可扩展，而且具有良好的功能组兼容性和基板范围。因此，我们的方案应允许通过开发硫代亚氨酸酯的新支架来扩展化学空间，而这些支架否则很难合成。
• Exploring unsymmetrical dyads as efficient inhibitors against the insect β-N-acetyl-d-hexosaminidase OfHex2
  作者：Qi Chen、Peng Guo、Lin Xu、Tian Liu、Xuhong Qian、Qing Yang

  DOI：10.1016/j.biochi.2013.10.008

  日期：2014.2

  The GH20 beta-N-acetyl-D-hexosaminidase OfHex2 from the insect Ostrinia furnacalis (Guenee) is a target potential for eco-friendly pesticide development. Although carbohydrate-based inhibitors against beta-Nacetyl-D-hexosaminidases are widely studied, highly efficient, non-carbohydrate inhibitors are more attractive due to low cost and readily synthetic manner. Based on molecular modeling analysis of the catalytic domain of OfHex2, a series of novel naphthalimide-scaffold conjugated with a small aromatic moiety by an alkylamine spacer linker were designed and evaluated as efficiently competitive inhibitors against OfHex2. The most potent one containing naphthalimide and phenyl groups spanning by an N-alkylamine linker has a K-i value of 0.37 mu M, which is 6 fold lower than that of M-31850, the most potent non-carbohydrate inhibitor ever reported. The straightforward synthetic manners as well as the presumed binding model in this paper could be advantageous for further structural optimization for developing inhibitors against GH20 beta-N-acetyl-D-hexosaminidases. (C) 2013 Elsevier Masson SAS. All rights reserved.