2,2-二甲基-3,4-二氢萘-1-酮 | 2977-45-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 2,2-二甲基-3,4-二氢萘-1-酮
• 中文别名: 2,2-二甲基-3,4-2H-1-萘酮
• 英文名称: 2,2-dimethyl-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: 2,2-Dimethyl-1-tetralon；2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one；2,2-Dimethyl-3,4-dihydronaphthalen-1-one
• CAS: 2977-45-9
• 化学式: C₁₂H₁₄O
• mdl: MFCD22565862
• 分子量: 174.243
• InChiKey: XNTNPKXCRBTDTR-UHFFFAOYSA-N

物化性质

• 沸点：
  137 °C
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温且干燥

反应信息

• 作为反应物：
  描述：

  2,2-二甲基-3,4-二氢萘-1-酮 在 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 3-(2,2-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Structure–Activity Relationships, Pharmacokinetics, and in Vivo Activity of CYP11B2 and CYP11B1 Inhibitors

  摘要：

  CYP11B2, the aldosterone synthase, and CYP11B1, the cortisol synthase, are two highly homologous enzymes implicated in a range of cardiovascular and metabolic diseases. We have previously reported the discovery of LCI699, a dual CYP11B2 and CYP11B1 inhibitor that has provided clinical validation for the lowering of plasma aldosterone as a viable approach to modulate blood pressure in humans, as well normalization of urinary cortisol in Cushing's disease patients. We now report novel series of aldosterone synthase inhibitors with single-digit nanomolar cellular potency and excellent physicochemical properties. Structure-activity relationships and optimization of their oral bioavailability are presented. An illustration of the impact of the age of preclinical models on pharmacokinetic properties is also highlighted. Similar biochemical potency was generally observed against CYP11B2 and CYP11B1, although emerging structure-selectivity relationships were noted leading to more CYP11B1-selective analogs.

  DOI：

  10.1021/acs.jmedchem.5b00407
• 作为产物：
  描述：

  2-(o-iodophenyl)ethyl methanesulfonate 在 palladium diacetate 正丁基锂 、 三乙胺 、 二异丙胺 、 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 25.0h， 生成 2,2-二甲基-3,4-二氢萘-1-酮
  参考文献：
  名称：

  腈的Carpalpallading：通过Pd催化ω-（2-碘芳基）烷腈和相关化合物的环化反应合成苯并酮和环戊烯酮。

  摘要：

  已经开发出一种通过腈的分子内碳弹头化合成2，2-二取代的苯并环酮的有效方法。取代的3-（2-碘芳基）丙烷腈的环化以高收率提供茚满酮。该反应与多种官能团相容。该方法已经扩展到四氢萘酮和环戊烯酮的合成。

  DOI：

  10.1021/jo0262006

文献信息

• Photochemistry of 2′-substituted 1,2,3,4-tetrahydronaphthalene-1-spiro-3′oxaziridines. Variable-temperature¹H nuclear magnetic resonance spectroscopy of 1-substituted 1,3,4,5-tetrahydro-2H-1-benzazepin-2-ones
  作者：Graham P. Johnson、Brian A. Marples

  DOI：10.1039/p19880003399

  日期：——

  The lack of regioselectivity of photorearrangement of the title spiro-oxaziridines in which the N-substituent is syn to the aromatic ring suggests that the first formed N–O–bond-cleaved species has a significant lifetime allowing rotation (inversion) to compete with rearrangement. The energy barrier to ring inversion of the title tetrahydro-1-benzazepin-2-ones is significantly influenced by the steric

  缺少其中的标题螺-氧氮环丙烷的photorearrangement的区域选择性ñ -取代的顺式与芳香环表明先形成N-O键裂解物种具有显著寿命允许的旋转（反转）与重排竞争。N-取代基与周围氢原子之间的空间相互作用显着影响标题四氢-1-苯并ze庚因-2-酮环转化的能垒。
• [EN] 5-HT2C RECEPTOR AGONISTS AND COMPOSITIONS AND METHODS OF USE<br/>[FR] AGONISTES DE RÉCEPTEUR 5-HT2C ET COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：ARENA PHARM INC

  公开号：WO2017023679A1

  公开（公告）日：2017-02-09

  Provided in some embodiments are compounds of Formula A, as defined herein, that modulate the activity of 5-HT2C receptor. Also provided in some embodiments are methods, such as, for weight management, inducing satiety, and decreasing food intake, and for preventing and treating obesity, antipsychotic-induced weight gain, type 2 diabetes, Prader-Willi syndrome, tobacco/nicotine dependence, drug addiction, alcohol addiction, pathological gambling, reward deficiency syndrome, and sex addiction), obsessive-compulsive spectrum disorders and impulse control disorders (including nail-biting and onychophagia), sleep disorders (including insomnia, fragmented sleep architecture, and disturbances of slow-wave sleep), urinary incontinence, psychiatric disorders (including schizophrenia, anorexia nervosa, and bulimia nervosa), Alzheimer disease, sexual dysfunction, erectile dysfunction, epilepsy, movement disorders (including parkinsonism and antipsychotic-induced movement disorder), hypertension, dyslipidemia, nonalcoholic fatty liver disease, obesity-related renal disease, and sleep apnea.

  在某些实施例中提供了一些符合本文所定义的A式化合物，其调节5-HT2C受体的活性。在某些实施例中还提供了一些方法，例如用于体重管理、诱导饱腹感、减少食物摄入，以及预防和治疗肥胖、抗精神病药物引起的体重增加、2型糖尿病、普拉德-威利综合征、烟草/尼古丁依赖、药物成瘾、酒精成瘾、病理性赌博、奖赏缺乏综合征和性成瘾，强迫症谱系障碍和冲动控制障碍（包括咬指甲和咬甲症），睡眠障碍（包括失眠、睡眠结构碎裂和慢波睡眠紊乱），尿失禁，精神障碍（包括精神分裂症、厌食症和暴食症），阿尔茨海默病，性功能障碍，勃起功能障碍，癫痫，运动障碍（包括帕金森病和抗精神病药物引起的运动障碍），高血压，血脂异常，非酒精性脂肪肝病，肥胖相关肾脏疾病和睡眠呼吸暂停症。
• Enantioselective Borohydride Reduction Catalyzed by Optically Active Cobalt Complexes
  作者：Tohru Yamada、Takushi Nagata、Kiyoaki D. Sugi、Kiyotaka Yorozu、Taketo Ikeno、Yuhki Ohtsuka、Daichi Miyazaki、Teruaki Mukaiyama

  DOI：10.1002/chem.200304794

  日期：2003.9.22

  enantioselective borohydride reduction of aromatic ketones or imines to the corresponding alcohols was developed in the presence of a catalytic amount of an optically active cobalt(II) complex catalyst. This enantioselective reduction is carried out using a precisely premodified borohydride with alcohols such as tetrahydrofurfuryl alcohol, ethanol and methanol. High optical yields are obtained by choosing

  在催化量的光学活性钴（II）络合物催化剂的存在下，芳香族酮或亚胺对映体的高度对映选择性硼氢化物还原。该对映选择性还原是使用精确预改性的硼氢化物与醇（例如四氢糠醇，乙醇和甲醇）进行的。通过选择合适的醇作为改性剂和合适的催化剂β-酮亚氨基配体，可以获得高的光学收率。对映选择性硼氢化物还原已成功应用于光学活性的1,3-二醇的制备，双酰基二茂铁的立体选择性还原以及1,3-二羰基化合物的动态和/或动力学拆分。
• Scandium(III) Triflate Catalyzed Direct Synthesis of <i>N</i>-Unprotected Ketimines
  作者：Yuta Kondo、Tetsuya Kadota、Yoshinobu Hirazawa、Kazuhiro Morisaki、Hiroyuki Morimoto、Takashi Ohshima

  DOI：10.1021/acs.orglett.9b04038

  日期：2020.1.3

  intermediates for synthesizing valuable nitrogen-containing compounds, but their potential applicability is limited by the available synthetic methods. To address this issue, we report a scandium(III) triflate catalyzed direct synthesis of N-unprotected ketimines. Using commercially available reagents and Lewis acid catalysts, ketones were directly transformed into the corresponding N-unprotected ketimines

  N-未保护的酮亚胺是用于合成有价值的含氮化合物的有用底物和中间体，但其潜在的适用性受到可用合成方法的限制。为了解决这个问题，我们报告了三氟甲磺酸（（III）催化的N-未保护酮亚胺的直接合成。使用可商购的试剂和路易斯酸催化剂，将酮以高收率直接转化为相应的N-未保护的酮亚胺，具有宽泛的官能团耐受性，甚至以毫克计。该反应易于用于重要化合物（例如甘氨酸席夫碱）的一锅合成，而无需分离N-未保护的酮亚胺中间体。还介绍了初步的机理研究以阐明反应机理。
• Co(acac)2-Catalyzed Allylic and Benzylic Oxidation by tert-Butyl Hydroperoxide
  作者：Yumei Xiao、Zhaohai Qin、Xiaoqiang Han、Ziyuan Zhou、Chuan Wan

  DOI：10.1055/s-0032-1318172

  日期：——

  Abstract Various allylic and benzylic substrates were oxidized to the corresponding enones, arenealdehydes and aryl ketones in good yields with tert-butyl hydroperoxide in the presence of catalytic amounts of Co(acac)2 under mild conditions. The reactivity, selectivity, and scope of the reaction were investigated. Various allylic and benzylic substrates were oxidized to the corresponding enones, arenealdehydes

  摘要 在温和的条件下，在催化量的Co（acac）2存在下，用叔丁基氢过氧化物将各种烯丙基和苄基底物氧化成相应的烯酮，戊烯醛和芳基酮，产率很高。研究了反应性，选择性和反应范围。 在温和的条件下，在催化量的Co（acac）2存在下，用叔丁基氢过氧化物将各种烯丙基和苄基底物氧化成相应的烯酮，戊烯醛和芳基酮，产率很高。研究了反应性，选择性和反应范围。