5,6-dimethoxy-indan-1,2-dione-2-oxime | 2107-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5,6-dimethoxy-indan-1,2-dione-2-oxime
• 英文别名: 5,6-dimethoxy-2-oximino-1-indanone；5,6-dimethoxy-1,2-indanedione 2-oxime；2-(hydroxyimino)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one；2-hydroxyimino-5,6-dimethoxy-3H-inden-1-one
• CAS: 2107-85-9
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: AXBBGHFTZOZJHA-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C
• 沸点：
  437.6±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  5,6-dimethoxy-indan-1,2-dione-2-oxime 在 platinum(IV) oxide 、 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 5,6-dimethoxy-2-(2-propylamino)indan
  参考文献：
  名称：

  Conformationally restricted congeners of dopamine derived from 2-aminoindan

  摘要：

  Two series of N-substituted 2-aminoindan systems have been prepared: 4,5-dihydroxy-2-aminoindan (1) has a hydroxylation pattern analogous to the alpha conformer of dopamine, and 5,6-dihydroxy-2-aminoindan (2) has a hydroxylation pattern of the beta conformer of dopamine. All members of both series demonstrated only extremely weak binding to calf caudate homogenate. Certain N-alkylated 4,5-dihydroxyindans were violent emetics in the dog and were potent in blockade of the effect of stimulation of the cardioaccelerator nerve of the cat. In contrast, the 5,6-dihydroxy series displayed low or no activity/potency in these assays. Conformational analysis of the 2-aminoindan system is described and discussed.

  DOI：

  10.1021/jm00354a010
• 作为产物：
  描述：

  3,4-二甲氧基苯丙酸 在 盐酸 、 PPA 、 亚硝酸乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 5,6-dimethoxy-indan-1,2-dione-2-oxime
  参考文献：
  名称：

  Simchen,G.; Kraemer,W., Chemische Berichte, 1969, vol. 102, p. 3656 - 3665

  摘要：

  DOI：

文献信息

• Cu-catalyzed coupling of indanone oxime acetates with thiols to 2,3-difunctionalized indenones
  作者：Yuanyuan Fu、Xueyan Zhao、Dengfeng Chen、Jinyue Luo、Shenlin Huang

  DOI：10.1039/d1cc04167c

  日期：——

  A Cu-catalyzed coupling reaction of indanone oxime acetates with thiols has been developed for the synthesis of 2,3-functionalized 1-indenones. This protocol has several features including easy mild reaction conditions, stabilized enamine products, good tolerance of functional groups, and no external oxidants. This reaction enables direct derivatization on the indanone ring to provide valuable functionalized

  茚满酮肟乙酸酯与硫醇的 Cu 催化偶联反应已被开发用于合成 2,3-功能化 1-茚酮。该协议有几个特点，包括容易温和的反应条件、稳定的烯胺产品、良好的官能团耐受性和无外部氧化剂。该反应能够在茚满酮环上直接衍生化，从而在室温下提供有价值的官能化茚酮。
• [EN] SMALL MOLECULE AGONISTS OF NEUROTENSIN RECEPTOR 1<br/>[FR] AGONISTES À PETITES MOLÉCULES DE RÉCEPTEUR DE NEUROTENSINE 1
  申请人：SANFORD BURNHAM MED RES INST

  公开号：WO2014100501A1

  公开（公告）日：2014-06-26

  Provided herein are small molecule neurotensin receptor agonists, compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

  提供的是小分子神经降压素受体激动剂，包含这些化合物的组合物，以及使用这些化合物和包含这些化合物的组合物的方法。
• Novel N-benzylpiperidine carboxamide derivatives as potential cholinesterase inhibitors for the treatment of Alzheimer's disease
  作者：Divan G. van Greunen、C. Johan van der Westhuizen、Werner Cordier、Margo Nell、Andre Stander、Vanessa Steenkamp、Jenny-Lee Panayides、Darren L. Riley

  DOI：10.1016/j.ejmech.2019.06.088

  日期：2019.10

  A series of fifteen acetylcholinesterase inhibitors were designed and synthesised based upon the previously identified lead compound 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl 1-benzylpiperidine-4-carboxylate (5) which showed good inhibitory activity (IC50 0.03 ± 0.07 μM) against acetylcholinesterase. A series of compounds were prepared wherein the ester linker in the original lead compound was

  根据先前确定的先导化合物5,6-二甲氧基-1-氧代-2,3-二氢-1H-茚满-2-基-1-苄基哌啶-4-羧酸酯设计并合成了十五种乙酰胆碱酯酶抑制剂系列（5）对乙酰胆碱酯酶显示出良好的抑制活性（IC 50 0.03±0.07μM）。制备了一系列化合物，其中将原始先导化合物中的酯连接基交换为代谢上更稳定的酰胺连接基，并将茚满酮部分交换为一系列芳基和芳族杂环。两个最活性类似物1-苄基- ñ - （5,6-二甲基-8H-茚并[1,2-d]噻唑-2-基）哌啶-4-甲酰胺（28）和1-苄基Ñ-（1-甲基-3-氧代-2-苯基-2,3-二氢-1H-吡唑-4-基）哌啶-4-甲酰胺（20）的体外IC 50值为0.41±1.25和5.94±1.08分别为μM。在计算机筛查中预测20将成为血脑屏障渗透物，分子动力学模拟表明20的结合与美国食品药品监督管理局批准的胆碱酯酶抑制剂多奈哌齐（1）紧密相关。
• Synthesis of 2-(Cyanomethyl)benzoic Esters via Carbon–Carbon Bond Cleavage of Indanones
  作者：Xiangtai Meng、Dengfeng Chen、Rui Liu、Ping Jiang、Shenlin Huang

  DOI：10.1021/acs.joc.1c01131

  日期：2021.8.6

  A novel synthesis of 2-(cyanomethyl)benzoic esters from indanone derivatives has been established. This reaction proceeds via a deprotonation of alcohols with a chemical base, followed by a nucleophilic addition to indanones and Beckmann fragmentation. In addition, this reaction could also work under electrochemical conditions, and no external chemical bases were needed. This mild method offers a novel

  已经建立了一种从茚满酮衍生物合成 2-(氰甲基) 苯甲酸酯的新方法。该反应通过醇与化学碱的去质子化进行，然后是茚满酮的亲核加成和贝克曼断裂。此外，该反应还可以在电化学条件下进行，不需要外部化学碱。这种温和的方法为各种天然醇的后期功能化提供了一种新策略。
• Synthesis and Biological Evaluation of 9-Oxo-9<i>H</i>-indeno[1,2-<i>b</i>]pyrazine-2,3-dicarbonitrile Analogues as Potential Inhibitors of Deubiquitinating Enzymes
  作者：Matteo Colombo、Stefania Vallese、Ilaria Peretto、Xavier Jacq、Jean-Christophe Rain、Frédéric Colland、Philippe Guedat

  DOI：10.1002/cmdc.200900409

  日期：2010.4.6

  (1) as an active inhibitor of ubiquitin‐specific proteases (USPs), a family of hydrolytic enzymes involved in the removal of ubiquitin from protein substrates. The chemical behavior of compound 1 was examined. Moreover, the synthesis and in vitro evaluation of new compounds, analogues of 1, led to the identification of potent and selective inhibitors of the deubiquitinating enzyme USP8.

  高通量筛选突出-9-氧代9 ħ -茚并[1,2 b ]吡嗪-2,3-二腈（1）作为泛素特异性蛋白酶的活性抑制剂（USPS），一个家庭参与水解酶的从蛋白质底物中去除泛素。检查了化合物1的化学行为。此外，新化合物（1的类似物）的合成和体外评估还导致了去泛素化酶USP8的有效和选择性抑制剂的鉴定。