ethyl 2-methyl-1-indanone-2-carboxylate | 91910-16-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: ethyl 2-methyl-1-indanone-2-carboxylate
• 英文别名: ethyl 2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate；1H-Indene-2-carboxylic acid, 2,3-dihydro-2-methyl-1-oxo-, ethyl ester；ethyl 2-methyl-3-oxo-1H-indene-2-carboxylate
• CAS: 91910-16-6
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: DCYDWCMLWSSBFA-UHFFFAOYSA-N

物化性质

• 熔点：
  31 °C
• 沸点：
  156 °C(Press: 14 Torr)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-1-indanone-2-carboxylate 在 samarium diiodide 、 氢溴酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 2-hydroxy-2,3-methano-3-methyl-1-oxo-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Novel transformation of 2-substituted alkyl 1-indanone-2-acetates to 6-substituted 3,4-benzotropolones through sequential reduction and oxidation processes using Sm(II) and Ce(IV) salts

  摘要：

  When 2-substituted alkyl 1-indanone-2-acetates 1 were treated with samarium diiodide, 3-substituted 2-hydroxy-2,3-methano-1-oxo-1,2,3,4-tetrahydronaphthalenes 4 were obtained. The reaction is proposed to proceed through a rearrangement initiated by intramolecular ketone-ester coupling. Oxidation of these products 4 or their silyl ethers 13 by ceric(IV) ammonium nitrate involving regioselective bond cleavage of their bicyclo[4.1.0]-rings produced the corresponding benzotropolone derivatives 10. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.083
• 作为产物：
  描述：

  乙基1-氧亚基-2,3-二氢-1H-茚-2-甲酸基酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 oil 为溶剂， 反应 3.5h， 生成 ethyl 2-methyl-1-indanone-2-carboxylate
  参考文献：
  名称：

  甲硅烷基醚的有机催化对映选择性质子化：范围，局限性和在制备富含对映异构体的黄酮类化合物中的应用

  摘要：

  在目前的工作中，据报道在各种质子亲核试剂作为质子源的情况下，通过多种手性氮碱作为催化剂，主要衍生自金鸡纳生物碱，对甲硅烷基烯醇醚进行对映选择性质子化。公开了对最相关的反应参数的详细研究，从而允许在温和和环境友好的条件下实现高达92％ee的高对映选择性和极佳的收率。此有机催化质子化的合成效用制备两个homoisoflavones期间展示图4a和4b中，从分离吊兰Inornatum和绵性厌食症，其分别用81％和78％ee的，获得的。

  DOI：

  10.1021/jo101585t

文献信息

• Samarium diiodide-promoted intramolecular ketone–ester coupling reaction: novel cyclization and ring expansion pathway
  作者：Kazuki Iwaya、Momoe Nakamura、Eietsu Hasegawa

  DOI：10.1016/s0040-4039(02)01007-9

  日期：2002.7

  2-substituted-1-indanone-2-carboxylates were treated with samarium diiodide (SmI2), ring expansion products such as 3-substituted-1,2-naphthoquinones were isolated. Alcohols were also obtained as the mixture of cis- and trans-isomers of hydroxy and ester substituents. A reaction mechanism involving intramolecular addition of samarium ketyl radicals to ester substituents followed by ring expansion was proposed

  当用二碘化（（SmI 2）处理2-取代的1-茚满酮-2-羧酸乙酯时，分离出诸如3-取代的1,2-萘醌的扩环产物。还获得了羟基和酯取代基的顺式和反式异构体的混合物的醇。提出了一种将mechanism酮基mar分子内加成到酯取代基上，然后进行环扩环的反应机理，以形成一碳均聚物。类似地，使1-取代的2-氧代-1-氧-1-环戊烷甲酸乙酯与SmI 2反应产生3-取代的-2-羟基-2-环己烯酮以及相应的醇。
• [EN] DUAL NAV1.2/5HT2A INHIBITORS FOR TREATING CNS DISORDERS<br/>[FR] INHIBITEURS DOUBLES DE NAV1.2/5HT2A POUR TRAITER DES TROUBLES DU SNC
  申请人：SUNOVION PHARMACEUTICALS INC

  公开号：WO2018026371A1

  公开（公告）日：2018-02-08

  Compounds of formula I: I are disclosed, as are pharmaceutical compositions containing such compounds. Methods of treating neurological or psychiatric disorders in a patient in need are also disclosed. Such disorders include depression, bipolar disorder, pain, schizophrenia, obsessive compulsive disorder, addiction, social disorder, attention deficit hyperactivity disorder, an anxiety disorder, autism, a cognitive impairment, or a neuropsychiatric symptom such as apathy, depression, anxiety, psychosis, aggression, agitation, impulse control disorders, and sleep disorders in neurological disorders such as Alzheimer's and Parkinson's diseases.

  公开了化学式I的化合物，以及含有这些化合物的药物组合物。还公开了治疗患有神经系统或精神障碍的患者的方法。这些障碍包括抑郁症、躁郁症、疼痛、精神分裂症、强迫症、成瘾、社交障碍、注意力缺陷多动障碍、焦虑障碍、自闭症、认知障碍，或神经精神症状，如冷漠、抑郁、焦虑、精神病、攻击性、激动、冲动控制障碍，以及在神经系统疾病如阿尔茨海默病和帕金森病中的睡眠障碍。
• Cyclization and Ring-Expansion Processes Involving Samarium Diiodide Promoted Reductive Formation and Subsequent Oxidative Ring Opening of Cyclopropanol Derivatives
  作者：Hiroyuki Tsuchida、Mutsuko Tamura、Eietsu Hasegawa

  DOI：10.1021/jo802749g

  日期：2009.3.20

  convert to cyclic conjugated enones in moderate to good yields. In addition, the reduction−oxidation reaction sequences can be successfully performed in one pot. The regioselectivities of cyclopropane ring opening in the bicyclic substrates depend on the oxidizing agents used. For example, reactions promoted by FeCl3 with pyridine lead to the expected ring-expansion process involving internal-bond cleavage

  io二碘化物促进了各种α-溴甲基环烷酮的反应，然后用三甲基甲硅烷基氯进行处理，导致嵌在双环[ m .1.0]烷烃骨架中的环丙基甲硅烷基醚的生产。用氧化性电子转移试剂（例如Fe（III），Ce（IV）和Mn（III）盐）处理醚时，会生成扩环酮，并以中等至良好的产率转化为环状共轭烯酮。另外，还原氧化反应序列可以在一锅中成功进行。双环底物中环丙烷开环的区域选择性取决于所用的氧化剂。例如，FeCl 3促进的反应用吡啶导致预期的扩环过程，该过程涉及双环烷烃的内部键裂解并产生环烯酮作为最终产物。相反，与Ce（NH 4）2（NO 3）6或Mn（OAc）3作为氧化剂的反应通过外键裂解进行，得到α-碘甲基环烷酮。
• Photoinduced electron-transfer reaction of α-bromomethyl-substituted benzocyclic β-keto esters with amines: selective reaction pathways depending on the nature of the amine radical cations
  作者：Eietsu Hasegawa、Emi Tosaka、Akira Yoneoka、Yukinobu Tamura、Shin-ya Takizawa、Masaaki Tomura、Yoshiro Yamashita

  DOI：10.1007/s11164-012-0646-2

  日期：2013.1

  with tertiary amines was investigated. Debrominated β-keto esters and ring-expanded γ-keto esters were obtained as major products. On the basis of mechanistic experiments it was concluded that these products are formed via a reaction sequence of selective carbon–bromine bond cleavage and subsequent competitive hydrogen abstraction and Dowd–Beckwith ring-expansion of the resulting primary alkyl radicals

  研究了α-溴甲基取代的苯并环β-酮酯与叔胺的光诱导电子转移反应。获得了主要产物脱溴的β-酮酯和扩环的γ-酮酯。根据机理实验得出的结论是，这些产物是通过选择性的碳-溴键裂解反应以及随后的竞争性氢提取和Dowd-Beckwith环扩环生成的一级烷基的反应序列形成的。对于所用胺类型观察到的特征产物分布是根据所产生的自由基中间体的选择性反应途径而合理化的，该途径取决于胺自由基阳离子的性质。
• Tris(trimethylsilyl)silane promoted radical reaction and electron-transfer reaction in benzotrifluoride
  作者：Eietsu Hasegawa、Yuki Ogawa、Koji Kakinuma、Hiroyuki Tsuchida、Emi Tosaka、Shinya Takizawa、Hiroyasu Muraoka、Tomoko Saikawa

  DOI：10.1016/j.tet.2008.06.012

  日期：2008.8

  Tris(trimethylsilyl)silane (TTMSS) promoted free radical reaction in benzotrifluoride (BTF) was investigated. Compared to same reaction using environmentally less desirable tri-n-butyltin hydride (TBTH) in benzene, less quantity of BTF than that of benzene can be used because of slower hydrogen atom transfer from TTMSS than that from TBTH toward primary alkyl radicals. Also, electron-transfer reactions

  研究了三（三甲基甲硅烷基）硅烷（TTMSS）在苯并三氟化物（BTF）中促进的自由基反应。使用环境不太理想的三-相对于相同的反应Ñ苯-butyltin氢化物（TBTH），BTF的比苯的可以因为来自TTMSS较慢氢原子转移比从TBTH朝向初级烷基的使用量较少。另外，在BTF中进行了由三（对-溴苯基）六氯锑酸铵（TBPA）和FeCl 3促进的电子转移反应。然后，发现TBPA在BTF中的效果与在二氯甲烷中的效果相当。另外，有趣的观察表明FeCl 3加入咪唑鎓盐可促进反应的进行。所有结果表明，BTF是与TTMSS进行自由基反应和使用TBPA以及FeCl 3进行电子转移反应的可耐受溶剂。