6-methoxy-2-methylene-3,4-dihydro-2H-naphthalen-1-one | 82875-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-methoxy-2-methylene-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: 3,4-Dihydro-6-methoxy-2-methylene-1(2h)-naphthalenone；6-methoxy-2-methylidene-3,4-dihydronaphthalen-1-one
• CAS: 82875-92-1
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: QJSMBFOQGUOWQJ-UHFFFAOYSA-N

物化性质

• 熔点：
  44-45.5 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  335.3±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

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：
  0.25
• 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：

  6-methoxy-2-methylene-3,4-dihydro-2H-naphthalen-1-one 生成 6',8-dimethoxyspiro[3,4,4a,5,6,10b-hexahydrobenzo[h]chromene-2,2'-3,4-dihydronaphthalene]-1'-one
  参考文献：
  名称：

  Collins David J., Fallon Gary D., Skene Colin E., Austral. J. Chem, 47 (1994) N 4, S 623-648

  摘要：

  DOI：
• 作为产物：
  描述：

  2-dimethylaminomethyl-6-methoxy-3,4-dihydronaphthalen-1(2H)-one hydrochloride 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 生成 6-methoxy-2-methylene-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Kulkarni, Y. D.; Agarwal, Vipin Kumar, Journal of the Indian Chemical Society, 1982, vol. 59, # 3, p. 380 - 382

  摘要：

  DOI：

文献信息

• Metal-free Michael addition initiated multicomponent oxidative cyclodehydration route to polysubstituted pyridines from 1,3-dicarbonyls
  作者：Frédéric Liéby-Muller、Christophe Allais、Thierry Constantieux、Jean Rodriguez

  DOI：10.1039/b805680c

  日期：——

  A simple metal-free, step-economic and selective access to pyridines from readily available substrates is reported, involving a flexible 4 A molecular sieves promoted Michael addition initiated domino three-component reaction between a 1,3-dicarbonyl, a Michael acceptor and a synthetic equivalent of ammonia.

  据报道，一种简单的无金属的，经济易行的，可选择性地从易于获得的底物上获得吡啶的方法，涉及一种灵活的4 A分子筛，该分子筛促进了1,3-二羰基，迈克尔受体和环戊烯之间的迈克尔加成引发的多米诺三组分反应。合成当量的氨。
• Metal-Free Michael-Addition-Initiated Three-Component Reaction for the Regioselective Synthesis of Highly Functionalized Pyridines: Scope, Mechanistic Investigations and Applications
  作者：Christophe Allais、Frédéric Liéby-Muller、Jean Rodriguez、Thierry Constantieux

  DOI：10.1002/ejoc.201300246

  日期：2013.7

  and completely regioselective three-component synthesis of highly functionalized pyridines from 1,3-dicarbonyl derivatives and Michael acceptors has been achieved. Activated Michael acceptors, that is, β,γ-unsaturated α-oxo carbonyl derivatives, were utilized, allowing substitution at the 4-position and remarkable functional diversity at the 2-position of the pyridine ring. The scope and limitations

  已经实现了由 1,3-二羰基衍生物和迈克尔受体合成高度官能化吡啶的无金属和完全区域选择性的三组分合成。利用活化的迈克尔受体，即 β,γ-不饱和 α-羰基衍生物，允许在吡啶环的 4 位取代和在 2 位显着的功能多样性。公开了这种环境友好的多米诺骨牌反应的范围和局限性，并提供了完整的实验数据，并讨论了机理研究的结果。
• Nitrogen-containing heterocyclic compounds as class III antiarrhythmic
  申请人：Merck & Co., Inc.

  公开号：US05215989A1

  公开（公告）日：1993-06-01

  Compounds of structural formula: ##STR1## wherein Ar is an aromatic ring, B is a cyclic moiety fused to Ar of 5-7 members, X and Y are bridging groups, Q is a nitrogen containing heterocycle, R.sup.2 and R.sup.3 are H, substituted or unsubtituted C.sub.1-3 alkyl, C.sub.1-3 alkoxy, N(R).sub.2, halogen, CF.sub.3 or R.sup.5 and R.sup.1 is H or an aryl group.

  结构式化合物：##STR1## 其中Ar是芳香环，B是与Ar融合的5-7个成员的环状基团，X和Y是桥接基团，Q是含氮杂环，R.sup.2和R.sup.3是H，取代或未取代的C.sub.1-3烷基，C.sub.1-3烷氧基，N(R).sub.2，卤素，CF.sub.3或R.sup.5，R.sup.1是H或芳基。
• Nitrogens containing heterocyclic compounds as class III antiarrhythmic
  申请人：Merck & Co., Inc.

  公开号：US05032598A1

  公开（公告）日：1991-07-16

  Compounds of structural formula: ##STR1## wherein Ar is an aromatic ring, B is a cyclic moiety fused to Ar of 5-7 members and Q is a nitrogen containing heterocycle, are antiarrhythmic agents.

  结构式化合物：##STR1## 其中 Ar 是芳香环，B 是与 Ar 融合的含有 5-7 个成员的环状基团，Q 是含氮杂环，是抗心律失常药物。
• Expedient synthesis of tricyclic benzopyran-2-ones via N-Heterocyclic carbene catalyzed annulation of enals to α-methylene cycloalkanones
  作者：D. Venkata Mani Padmaja、C.R. Sinu、Jagadeesh Krishnan、Rony Rajan Paul、Sunil Varughese、K.C. Seetha Lakshmi、Vijay Nair

  DOI：10.1016/j.tet.2015.08.062

  日期：2015.11

  important biologically active compounds. Synthesis of a series of tricyclic benzopyrans derivatives via N-Heterocyclic carbene (NHC) catalyzed annulation of enals to α-methylidenetetralones/chromanones is described. This reaction afforded the benzopyrans in high yield with aromatic as well as aliphatic enals.

  三环苯并吡喃是药用重要生物活性的化合物。通过一系列的三环苯并吡喃衍生物的合成ñ -杂环卡宾（NHC）催化enals到α-methylidenetetralones的环/二氢吡喃进行说明。该反应得到的苯并吡喃以高收率与芳族以及脂族enals。