(1-naphthylacetyl)diazomethane | 91822-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1-naphthylacetyl)diazomethane
• 英文别名: 1-Diazo-3-naphthalen-1-ylpropan-2-one
• CAS: 91822-58-1
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: UOGMBVJHSLUKPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  19.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1-naphthylacetyl)diazomethane 以 乙醚 、 乙腈 为溶剂， 反应 72.5h， 生成 1H-cyclopenta[a]naphthalen-2(3H)-one
  参考文献：
  名称：

  Nitric Oxide Cheletropic Traps (NOCTs) with Improved Thermal Stability and Water Solubility

  摘要：

  The search for nitric oxide cheletropic traps (NOCTs) of the 7,7,8,8-tetraalkyl-o-quinodimethane type which would have properties appropriate for monitoring the formation of nitric oxide in cell cultures and in vivo by magnetic resonance techniques is described. In addition to the necessary condition that a NOCT reacts rapidly with NO to yield a persistent nitroxide radical, two additional properties were sought: (i) thermal stability at the temperature of interest (37 degrees C) and (ii) water solubility. To these ends, a number of 1,1,3,3-tetraalkyl-2-indanones (and a related naphthalene derivative) were synthesized and subjected to UV photolysis in solution, a procedure which generally (though not in all cases) caused the elimination of carbon monoxide and formation of the corresponding o-quinodimethane. The thermal instability of many of these compounds is due to a 1,5-sigmatropic hydrogen atom transfer which, for example, converts 7,7,8,8-tetramethyl-o-quinodimethane (1) to o-isopropyll-alpha-methylstyrene(1P) with a half-life of only ca. 140 s at 37 degrees C. Several o-quinodimethanes were discovered which were, for all practical purposes, completely stable at 37 degrees C. The most suitable lipid-soluble NOCT discovered was 7-(2-indenyl)-7,8,8-trimethyl-o-quinodimethane (5), which is stable and reacts very rapidly with NO to form a persistent nitroxide. Various derivatives of 5 were also examined and found to be equally, or almost equally, effective NOCTs. Water solubility was explored by addition of water-solubilizing groups to the ring of 1. The carboxylic acid group, 13, was found to be particularly suitable, since the carboxylate anion 14 conferred excellent water solubility without,interfering with either the nitric oxide trapping reaction or the necessary photoelimination of carbon monoxide from the starting indanone. Of even greater importance, the carboxylate group had no apparent effect on the rate of the thermal 1,5-sigmatropic rearrangement; i.e., the rates of decay of 14 and 1 were equal within experimental error. It is concluded that NOCTs of the o-quinodimethane class having long lifetimes and a high reactivity toward NO can now be prepared with appropriate lipophilic, hydrophilic, or amphiphilic properties. These NOCTs should prove suitable for exploratory use in biological systems.

  DOI：

  10.1021/ja00086a010
• 作为产物：
  描述：

  1-萘乙酸 在 氯化亚砜 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 18.0h， 生成 (1-naphthylacetyl)diazomethane
  参考文献：
  名称：

  Nitric Oxide Cheletropic Traps (NOCTs) with Improved Thermal Stability and Water Solubility

  摘要：

  The search for nitric oxide cheletropic traps (NOCTs) of the 7,7,8,8-tetraalkyl-o-quinodimethane type which would have properties appropriate for monitoring the formation of nitric oxide in cell cultures and in vivo by magnetic resonance techniques is described. In addition to the necessary condition that a NOCT reacts rapidly with NO to yield a persistent nitroxide radical, two additional properties were sought: (i) thermal stability at the temperature of interest (37 degrees C) and (ii) water solubility. To these ends, a number of 1,1,3,3-tetraalkyl-2-indanones (and a related naphthalene derivative) were synthesized and subjected to UV photolysis in solution, a procedure which generally (though not in all cases) caused the elimination of carbon monoxide and formation of the corresponding o-quinodimethane. The thermal instability of many of these compounds is due to a 1,5-sigmatropic hydrogen atom transfer which, for example, converts 7,7,8,8-tetramethyl-o-quinodimethane (1) to o-isopropyll-alpha-methylstyrene(1P) with a half-life of only ca. 140 s at 37 degrees C. Several o-quinodimethanes were discovered which were, for all practical purposes, completely stable at 37 degrees C. The most suitable lipid-soluble NOCT discovered was 7-(2-indenyl)-7,8,8-trimethyl-o-quinodimethane (5), which is stable and reacts very rapidly with NO to form a persistent nitroxide. Various derivatives of 5 were also examined and found to be equally, or almost equally, effective NOCTs. Water solubility was explored by addition of water-solubilizing groups to the ring of 1. The carboxylic acid group, 13, was found to be particularly suitable, since the carboxylate anion 14 conferred excellent water solubility without,interfering with either the nitric oxide trapping reaction or the necessary photoelimination of carbon monoxide from the starting indanone. Of even greater importance, the carboxylate group had no apparent effect on the rate of the thermal 1,5-sigmatropic rearrangement; i.e., the rates of decay of 14 and 1 were equal within experimental error. It is concluded that NOCTs of the o-quinodimethane class having long lifetimes and a high reactivity toward NO can now be prepared with appropriate lipophilic, hydrophilic, or amphiphilic properties. These NOCTs should prove suitable for exploratory use in biological systems.

  DOI：

  10.1021/ja00086a010

文献信息

• Synthesis, pharmacology, and molecular modeling of novel 4-alkyloxy indole derivatives related to cannabimimetic aminoalkyl indoles (AAIs)
  作者：A.K Dutta、W Ryan、B.F Thomas、M Singer、D.R Compton、B.R Martin、R.K Razdan

  DOI：10.1016/s0968-0896(97)00111-9

  日期：1997.8

  Several novel 4-alkyloxy-aminoalkyl indole derivatives 3 were synthesized from 4-benzyloxyindole (1). Alkylation of 1 with 4-(2-chloroethyl)morpholine (NaH/HMPA) formed 2. Deprotection using palladium hydroxide on carbon/hydrogen followed by alkylation with the appropriate alkyl bromide gave the target compounds 3b-3j. In the synthesis of 3i and 3j, the appropriate alkyl bromides 13 and 17 were prepared

  由4-苄氧基吲哚（1）合成了几种新颖的4-烷氧基-氨基烷基吲哚衍生物3。用4-（2-氯乙基）吗啉（NaH / HMPA）将1烷基化。2.在碳/氢上用氢氧化钯脱保护，然后用适当的烷基溴烷基化，得到目标化合物3b-3j。在3i和3j的合成中，使用如方案3所示的加长序列，由市售的1-萘基溴化物9制备适当的烷基溴化物13和17。在受体结合测定和体内测试中，长链烷氧基化合物3g和3h（Ki = 127 nM）对CB1受体的亲和力比WIN 55,225低约16-35倍。但是，3h的药理特性与WIN 55,212相似。对这些类似物的SAR的检查表明，AAI中的萘基通过氧（醚键）从C-3位置移位到C-4会降低活性，这与以前的发现相反，即C-4上的萘羰基保留了活动。本工作指出了酮基在与受体相互作用中的作用的重要性。分子建模工作表明，尽管可以在δ9-THC和AAI之间进行关键结构特征的合理叠加，但是覆盖并不容
• Antiangiogenic and antitumor agents
  作者：Aleem Gangjee、Jie Yang、Michael A. Ihnat、Shekhar Kamat

  DOI：10.1016/j.bmc.2003.08.034

  日期：2003.11

  containing tyrosine kinases (RTK) are directly or indirectly involved in angiogenesis. Inhibition of these RTKs has provided a new paradigm in the treatment of tumors by restricting their growth and metastasis. We have designed, synthesized and evaluated eleven novel 2-amino-4-(3-bromoanilino)-6-substituted benzyl pyrrolo[2,3-d]pyrimidines as the first in a series of RTK inhibitors. These analogues were

  包含酪氨酸激酶（RTK）的几种不同类别的生长因子受体直接或间接参与血管生成。抑制这些RTKs通过限制其生长和转移为肿瘤的治疗提供了新的范例。我们设计，合成和评估了11种新颖的2-氨基-4-（3-溴苯胺基）-6-取代的苄基吡咯并[2,3-d]嘧啶，这是一系列RTK抑制剂中的第一个。通过与2，6-二氨基-4-嘧啶酮进行环缩合反应，由合适的α-溴甲基苄基酮合成这些类似物，得到2-氨基-4-氧代-6-取代的苄基吡咯并[2，3-d]嘧啶。将4-位氯化，然后用3-溴苯胺置换，得到目标化合物。在某些情况下，吡咯并[2，在氯化和置换然后脱保护之前，对3-d]嘧啶进行保护。这些化合物被评估为血管内皮生长因子受体VEGFR-2（Flk-1，KDR）和VEGFR-1（Flt-1）的抑制剂。表皮生长因子受体（EGFR）; 和血小板衍生的生长因子受体-β（PDGFR-beta）。还评估了选定的化合物对培养物中A43
• Rapid Interception of CnF2n+1(O)SO• Radical with Copper‐Based Carbene: A Novel Access to Perfluoroalkanesulfinate Ester
  作者：Xiaobing Wan、Hanghang Wang、Haiyan Li、Yonggao Zheng、Pengcheng Lian

  DOI：10.1002/chem.201805639

  日期：——

  established. Distinguished by wide substrate scopes and mild reaction conditions, this novel radical–carbene coupling reaction (RCC reaction) provides a fundamentally different and mechanistically interesting strategy for the synthesis of perfluoroalkanesulfinate esters.

  在此通信中，C n F 2 n +1（O）SO受到前所未有的拦截。已经建立了带有铜基卡宾的自由基。由于具有宽泛的底物范围和温和的反应条件，这种新颖的自由基-卡宾偶联反应（RCC反应）为全氟烷烃亚磺酸酯的合成提供了根本不同且机制有趣的策略。
• A New and Mild Heterogeneous Catalytic Decomposition of α-Diazo Carbonyl Compounds Using Montmorillonite or Zeolite
  作者：Sengodagounder Muthusamy、Srinivasarao Arulananda Babu、Chidambaram Gunanathan、Raksh Vir Jasra

  DOI：10.1055/s-2002-20452

  日期：——

  A very mild method of decomposition of various α-diazo carbonyl compounds 1 in the presence of environmentally attractive solid acids such as montmorillonite K-10 or zeolite H-Y in a heterogeneous manner to furnish α-hydroxy/alkoxy ketones in very good yield is reported. Interestingly, novel bicycloalkane-1,3-diones and 3-furanones were obtained as unusual products in the case of aliphatic/alicyclic α-diazo carbonyl compounds.

  报告采用一种非常温和的方法，在对环境有吸引力的固体酸（如蒙脱石 K-10 或沸石 H-Y）存在下，以异构方式分解各种δ-重氮羰基化合物 1，从而以非常好的收率得到δ-羟基/烷氧基酮。有趣的是，在脂肪族/脂环族 δ-重氮羰基化合物中，作为不常见的产物，获得了新型双环烷-1,3-二酮和 3-呋喃酮。
• Indium triflate: a mild and efficient Lewis acid catalyst for O–H insertion reactions of α-diazo ketones
  作者：Sengodagounder Muthusamy、Srinivasarao Arulananda Babu、Chidambaram Gunanathan

  DOI：10.1016/s0040-4039(02)00489-6

  日期：2002.4

  Facile O-H insertion reactions of alpha-diazo ketones with alcohols or benzenethiol have been developed in the presence of indium triflate as a catalyst. These reactions provided good yields of alpha-alkoxy ketones. A comparative study with other Lewis acids establishes the reactivity of indium triflate in O-H insertion reactions of alpha-diazo ketones. (C) 2002 Elsevier Science Ltd. All rights reserved.