5-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-one | 124688-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-one
• 英文别名: 2,2-dimethyl-5-methoxyindan-1-one；5-methoxy-2,2-dimethyl-1-indanone；5-Methoxy-2,2-dimethylindanone；5-methoxy-2,2-dimethyl-3H-inden-1-one
• CAS: 124688-06-8
• 化学式: C₁₂H₁₄O₂
• mdl: MFCD11219439
• 分子量: 190.242
• InChiKey: ZENPNFPJVPODJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-one 在 三氟甲磺酸 、 二异丁基氢化铝 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 6.0h， 生成 (E)-4-(5-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-ylidene)-1-methyl-3,4-dihydro-2H-pyrrolium chloride
  参考文献：
  名称：

  Toward a Stable α-Cycloalkyl Amino Acid with a Photoswitchable Cationic Side Chain

  摘要：

  The N-alkylated indanylidenepyrroline (NAIP) Schiff base 3 is an unnatural a-amino acid precursor potentially useful for the preparation of semisynthetic peptides and proteins incorporating charged side chains whose structure can be modulated via Z/E photoisomerization. Here we report that the heteroallylic protons of 3 led to partial loss of ethanol accompanied by formation of the novel heterocyclic system 4 during attempted deprotection. We also show that the same protons catalyze the thermal isomerization of 3, making the light-driven conformational control concept ineffective for times longer than a few hours. These problems are not present in the previously unreported compound 5 where the acidic methyl group is replaced by an H atom. Therefore, 5, rather than 3, constitutes a promising prototype for the design of building blocks capable to modulate the electrostatic potential of a protein in specific locations via light irradiation.

  DOI：

  10.1021/jo2022263
• 作为产物：
  描述：

  2,2-dimethyl-5-methhoxyindan-1-ol 在 citrate buffer 、 potassium 12-tungstocobalt(III)ate 作用下， 生成 5-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  立体电子效应对烷基芳族自由基阳离子的侧链断裂的作用。5-甲氧基-2,2-二甲基茚满-1-醇自由基阳离子的反应性

  摘要：

  对2,2-二甲基-5-甲氧基茚满-1-醇（1）自由基阳离子在酸性水溶液（pH≤4）中的反应进行了动力学和产物研究。1 +作为唯一的反应经历CH质子去质子化，k = 4.6×10 4  s -1。动力学数据已与1-（4-甲氧基苯基）乙醇（2）和1-（4-甲氧基苯基）-2,2-二甲基-1-丙醇（3），表明当C–H键被迫形成几乎与π系统对齐的构象时，去质子率增加。1 +和3 +的DFT计算结果也支持了可裂键与π系统重叠是发生键断裂的重要条件的结论。

  DOI：

  10.1016/s0040-4020(02)00468-4

文献信息

• Catalytic C(sp²)–C(sp³) Bond Formation of Methoxyarenes by the Organic Superbase <i>t</i>-Bu-P4
  作者：Masanori Shigeno、Kazutoshi Hayashi、Kanako Nozawa-Kumada、Yoshinori Kondo

  DOI：10.1021/acs.orglett.0c03507

  日期：2020.11.20

  [cyano, nitro, (non)enolizable ketone, chloride, and amide moieties] are allowed on methoxyarenes. Moreover, an array of alkanenitriles with/without an aryl moiety at the nitrile α-position can be employed. The system also features no requirement of a stoichiometric base, MeOH (not salt waste) formation as a byproduct, and the production of congested quaternary carbon centers.

  有机超碱催化剂t -Bu-P4实现了烷烃前亲核体对甲氧基芳烃的亲核芳族取代。在甲氧基芳烃上可以使用各种官能团[氰基，硝基，（不可）烯化的酮，氯和酰胺部分）。此外，可以使用在腈α-位具有/不具有芳基部分的链烷腈的阵列。该系统还不需要化学计量的碱，不需要的副产物MeOH（无盐废料）形成以及拥挤的季碳中心的生产。
• Studies on synthesis and photoreaction of tricycloundecanes endowed with β,γ-enone chromophore: Towards angular triquinanes and annulated bicyclo[4.2.0]octanes
  作者：Raghaba Sahu、Vishwakarma Singh

  DOI：10.1016/j.tet.2017.09.040

  日期：2017.11

  Cycloaddition of annulated cyclohexa-2,4-dienone with electron deficient π-partners leading to tricycloundecanes having a β,γ-enone chromophore has been reported. Studies on the photochemical reaction of the chromophoric systems upon sensitized and direct irradiation has also been presented. A highly unusual behavior of the chromophoric systems upon sensitized irradiation has also been presented.

  已经报道了环状的环己-2，4-二烯酮与缺乏电子的π-伙伴的环加成反应导致具有β，γ-烯酮发色团的三环十一烷。还提出了发色体系在敏化和直接照射下的光化学反应的研究。还提出了发色系统在敏化辐射下的非常不正常的行为。
• Indole derivative having piperidine ring
  申请人：Suzuki Yuichi

  公开号：US20050256103A1

  公开（公告）日：2005-11-17

  The present invention relates to a compound represented by the following formula, a pharmacologically acceptable salt thereof, or a use thereof as a pharmaceutical: wherein R 1 and R 2 are substituents adjacent to each other, and together with two carbon atoms to each of which they attach, form a 5- to 7-membered non-aromatic carbocyclic group or the like, which may be substituted by 1 to 4 substituents selected from (1) an oxo group, (2) a hydroxyl group, and the like; R 3 represents a hydrogen atom or the like; and R 6 represents a hydrogen atom or the like. It is an object of the present invention to discover an agent for treating or preventing lower urinary tract symptoms, and particularly symptoms regarding urinary storage, which has a superior strength of binding to a 5-HT1A receptor and an antagonism to the receptor.

  本发明涉及以下公式所代表的化合物，其药学上可接受的盐，或其作为药物的用途： 其中R1和R2是相邻的取代基，与它们各自连接的两个碳原子一起形成一个5-至7-成员非芳香碳环基或类似物，该基可能被1至4个取代基所取代，所述取代基选自（1）氧代基，（2）羟基等；R3代表氢原子或类似物；R6代表氢原子或类似物。 本发明的目的是发现一种用于治疗或预防下尿道症状，特别是涉及尿液储存的症状的药剂，该药剂具有优越的结合力与5-HT1A受体结合并对该受体具有拮抗作用。
• FLUOROALLYLAMINE DERIVATIVE AND USE THEREOF
  申请人：Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd.

  公开号：EP3617186A1

  公开（公告）日：2020-03-04

  The present invention relates to a fluoroallylamine derivative and use thereof. In particular, the present invention relates to a compound as shown in Formula I, a prodrug, an isomer, an isotope-labeled compound, a solvate or a pharmaceutically acceptable salt thereof, which has VAP-1/SSAO inhibitory activity, and can be used for treating a disease associated with VAP-1/SSAO overactivity.

  本发明涉及一种氟烯丙胺衍生物及其用途。具体而言，本发明涉及一种如化学式I所示的化合物，一种前药、异构体、同位素标记化合物、溶剂合物或其药学上可接受的盐，具有VAP-1/SSAO抑制活性，并可用于治疗与VAP-1/SSAO过度活性相关的疾病。
• Synthesis of 1,4-Naphthoquinone Methides via Acid-Catalyzed Cascade Cyclizations of Benzannulated Enediynyl Alcohols
  作者：Bo Wen、Jeffrey L. Petersen、Kung K. Wang

  DOI：10.1021/ol102793a

  日期：2011.1.7

  benzannulated enediynyl alcohols with trifluoroacetic acid at room temperature promoted a cascade sequence of cyclization reactions, leading to 1,4-naphthoquinone methides. The transformation involved an unusual two-carbon ring expansion from the cyclic alcohols and the construction of the p-quinone methide ring from an acyclic system along the reaction pathway.

  在室温下用三氟乙酸处理苯并二烯化炔醇可以促进环化反应的级联序列，从而生成1,4-萘醌甲基化物。该转化涉及从环醇中不寻常的二碳环膨胀和沿着反应路径从无环系统构建对苯二甲酰甲基环。