1-(3,4-二氢萘-2-基)乙酮 | 76181-34-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(3,4-二氢萘-2-基)乙酮
• 英文名称: 2-acetyl-3,4-dihydronaphthalene
• 英文别名: 1-(3,4-dihydro-[2]naphthyl)-ethanone；1-(3,4-Dihydro-[2]naphthyl)-aethanon；1-(3,4-Dihydronaphthalen-2-yl)ethan-1-one；1-(3,4-dihydronaphthalen-2-yl)ethanone
• CAS: 76181-34-5
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: HHLYFOFIPKVXNS-UHFFFAOYSA-N

物化性质

• 沸点：
  173-175 °C(Press: 15 Torr)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3,4-二氢萘-2-基)乙酮 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以90%的产率得到2-萘乙酮
  参考文献：
  名称：

  Fleming, Ian; Pearce, Andrew, Journal of the Chemical Society. Perkin transactions I, 1980, p. 2485 - 2489

  摘要：

  DOI：
• 作为产物：
  描述：

  2-acetyl-1-hydroxy-1-trimethylsilyltetrahydronaphthalene 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.0h， 以96%的产率得到1-(3,4-二氢萘-2-基)乙酮
  参考文献：
  名称：

  Fleming, Ian; Pearce, Andrew, Journal of the Chemical Society. Perkin transactions I, 1980, p. 2485 - 2489

  摘要：

  DOI：

文献信息

• [EN] 2, 3, 6-TRISUBSTITUTED-4-PYRIMIDONE DERIVATIVES<br/>[FR] DERIVES DE 2,3,6-TRISUBSTITUE 4-PYRIMIDONE
  申请人：MITSUBISHI PHARMA CORP

  公开号：WO2004085408A1

  公开（公告）日：2004-10-07

  A pyrimidone derivative having tau protein kinase 1 inhibitory activity which is represented by formula (I) or a salt thereof, or a solvate thereof or a hydrate thereof; useful for prventive and/or therapeutic treatment of diseass such as neurodegenerative diseases (e.g. Alzheimer disease); wherein Q represents CH or nitrogen atom; R represents a C1-C12 alkyl group; the ring of Formula (I): represents piperazine ring or piperidine ring; each X independently represents a C1-C8 alkyl group, an optionally partially hydrogenated C6-C10 aryl ring, an indan ring or the like; m represents an integer of 1 to 3; each Y independently represents a halogen atom, a hydroxy group, a cyano group, a C1-C6 alkyl group or the like; n represents an integer of 0 to 8; when X and Y or two Y groups are attached on the same carbon atom, they may combine to each other to form a C2-C6 alkylene group.

  一种具有tau蛋白激酶1抑制活性的嘧啶酮衍生物，其由化学式（I）或其盐、溶剂合物或水合物表示；用于预防和/或治疗神经退行性疾病（例如阿尔茨海默病）；其中Q代表CH或氮原子；R代表C1-C12烷基基团；化学式（I）的环：代表哌嗪环或哌啶环；每个X独立地代表C1-C8烷基基团、可选择性部分氢化的C6-C10芳环、茚环或类似物；m代表1到3的整数；每个Y独立地代表卤素原子、羟基、氰基、C1-C6烷基基团或类似物；n代表0到8的整数；当X和Y或两个Y基团连接在同一碳原子上时，它们可以结合形成C2-C6烷基基团。
• Free radical annulation of dichlorocyclobutanones with sequential ring expansion
  作者：Paul Dowd、Wei Zhang、Steven J. Geib

  DOI：10.1016/0040-4020(95)00093-n

  日期：1995.3

  reaction of dichloroketene with 1,5-dienes undergo intramolecular free radical annulation. Lewis acid-promoted ring-opening of the cyclized cyclobutanones then yields novel ring expansion products. Reaction of (R)-carvone provides an unusual example leading to the formation of a tricyclic dione. The carbonyl group of carvone enhances the radical cyclization and influences the ring-opening pathway.

  描述了一种新的合成序列，该序列在1，5-二烯的末端添加了烯酮的元素。由二氯乙烯酮与1，5-二烯反应产生的二氯环丁酮加合物经历分子内自由基环化。然后路易斯酸促进环化环丁酮的开环，产生新的扩环产物。（R）-香芹酮的反应提供了导致形成三环二酮的不寻常的例子。香芹酮的羰基增强自由基环化并影响开环途径。
• Asymmetric reduction of αβ-unsaturated ketones with lithium aluminium hydride partially decomposed by (–)-N-methylephedrine and N-ethylaniline
  作者：Shiro Terashima、Norihiko Tanno、Kenji Koga

  DOI：10.1039/c39800001026

  日期：——

  The title asymmetric reaction is found to convert open chain enones into the corresponding optically active allylic alcohols in high optical (78–98% enantiomeric excess) and chemical (92–100%) yields.

  发现标题不对称反应可将开链烯酮转化为相应的旋光烯丙基醇，并具有较高的光学收率（对映体过量78-98％）和化学收率（92-100％）。
• Asymmetric reduction of various types of ketones with lithium aluminum hydride partially decomposed with (-)-N-methylephedrine and N-ethylaniline.
  作者：NORIHIKO TANNO、SHIRO TERASHIMA

  DOI：10.1248/cpb.31.837

  日期：——

  The asymmetric reduction of open chain enones to the corresponding optically active allylic alcohols was achieved in higher chemical (92-100%) and optical (78-98% e.e.) yields than those for cyclic enones (58-88% chemical and 34-58% optical yields). The observed high optical yields for optically active allylic alcohols can be explained on the assumption that, unlike cyclic enones in which the double bonds are fixed in s-trans conformation, open chain enones can be reduced in their s-cis conformations. An optically active propargylic alcohol was similarly produced from an ynone in 88% chemical and 76% optical yields by means of the present asymmetric reduction. When the same asymmetric reduction was applied to simple aromatic and aliphatic ketones by using 1.8 eq of the chiral reducing agent, the corresponding optically active alcohols were obtained in 88-100% chemical and 51-90% optical yields (for aromatic ketones) and in 78-98% chemical and 0-67% optical yields (for aliphatic ketones). On the basis of the results obtained in this and the preceding paper, a possible structure of the exploited chiral reducing agent is proposed and the transition states for the asymmetric reduction are discussed.

  开放链烯酮的不对称还原反应成功将其转化为相应的光学活性烯丙醇，化学产率（92-100%）和光学产率（78-98% e.e.)均高于环状烯酮（化学产率为58-88%，光学产率为34-58%）。相应的光学活性烯丙醇高的光学产率可以解释为，与固定在s-trans构象中的环状烯酮不同，开放链烯酮可以在其s-cis构象中进行还原。通过本不对称还原法，从一种炔酮中也成功获得了光学活性的丙炔醇，化学产率为88%，光学产率为76%。当对简单的芳香酮和脂肪酮应用相同的不对称还原，使用1.8倍当量的手性还原剂时，得到的相应光学活性醇的化学产率为88-100%（芳香酮）和78-98%（脂肪酮），光学产率分别为51-90%（芳香酮）和0-67%（脂肪酮）。基于本研究及前一篇论文中获得的结果，提出了所利用的手性还原剂的可能结构，并讨论了不对称还原的过渡态。
• Catalytic 1,2-dihydronaphthalene and <i>E</i>-aryl-diene synthesis <i>via</i> Co^III–Carbene radical and <i>o</i>-quinodimethane intermediates
  作者：Colet te Grotenhuis、Braja G. Das、Petrus F. Kuijpers、Wouter Hageman、Mees Trouwborst、Bas de Bruin

  DOI：10.1039/c7sc03909c

  日期：——

  yields for substrates with an R2 = COOEt substituent at the vinylic position (~70-90% ). Changing the R2 moiety from an ester to other substituents has a surprisingly large influence on the (isolated) yields. This behaviour is unexpected for a radical rebound ring-closure mechanism, and points to a mechanism proceeding via ortho-quinodimethane (o-QDM) intermediates. Furthermore, substrates with an alkyl

  提出了通过邻苯乙烯基 N-甲苯磺酰腙（( E )-2-(丙-1-烯-1-基)苯-N-甲苯磺酰腙）的金属自由基活化催化合成取代的1,2-二氢萘，钴(III)-卡宾自由基中间体的固有反应性。该方法已成功应用于芳香环上具有各种 R1 取代基的各种底物，对于乙烯基位置上具有 R 2 = COOEt 取代基的底物（约 70-90 %）。将R 2部分从酯变为其他取代基对（分离的）产率具有令人惊讶的巨大影响。这种行为对于自由基回弹闭环机制来说是出乎意料的，并且表明是通过邻醌二甲烷（o -QDM）中间体进行的机制。此外，在烯丙位上具有烷基取代基的底物以优异的产率反应形成E-芳基二烯，而不是预期的1,2-二氢萘。这一结果与支持 DFT 计算的结果相结合，强烈表明在所有情况下都会从金属中心释放反应性 o-QDM 中间体，这些中间体要么经历 6π 环化步骤形成 1,2-二氢萘，要么经过[1,7]-氢化物移位产生E-芳基二烯。使用