N-methyl-N-(5,6,7,8-tetrahydro-5-oxo-2-naphthyl)acetamide | 149456-02-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: N-methyl-N-(5,6,7,8-tetrahydro-5-oxo-2-naphthyl)acetamide
• 英文别名: N-(1,2,3,4-tetrahydro-1-oxonaphthalen-6-yl)-N-methylacetamide；Acetamide, N-methyl-N-(5,6,7,8-tetrahydro-5-oxo-2-naphthalenyl)-；N-methyl-N-(5-oxo-7,8-dihydro-6H-naphthalen-2-yl)acetamide
• CAS: 149456-02-0
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: ZMERYOJBRBDPDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-N-(5,6,7,8-tetrahydro-5-oxo-2-naphthyl)acetamide 在 copper(ll) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以30%的产率得到N-(2-bromo-1,2,3,4-tetrahydro-1-oxonaphthalen-6-yl)-N-methylacetamide
  参考文献：
  名称：

  氯化钛促进微波条件下新型咪唑并[1,2-a]吡啶衍生物的合成

  摘要：

  描述了一种由 2-氨基吡啶与 α-卤代酮反应合成咪唑并[1,2-a]吡啶衍生物的新方法。关键试剂是氯化钛 (IV)，它似乎是一种强脱水剂，可促进推定的席夫碱中间体的形成，后者随后环化形成产物。反应在微波条件下快速进行。评估了多种反应条件，包括反应温度、溶剂和其他路易斯酸。检查了 α-卤代酮和 2-氨基吡啶底物中取代模式的各种组合，以评估反应的范围。该反应对两种底物中的取代基都非常敏感，尤其是那些具有碱性或配位能力的底物。

  DOI：

  10.1055/s-2005-918490
• 作为产物：
  描述：

  5,6,7,8-四氢萘-2-基乙胺 在 chromium(VI) oxide 、 sodium hydride 作用下， 以 水 、 溶剂黄146 、 苯 为溶剂， 反应 20.0h， 生成 N-methyl-N-(5,6,7,8-tetrahydro-5-oxo-2-naphthyl)acetamide
  参考文献：
  名称：

  Allylindation of 6-Substituted 2-Hydroxy-1-tetralones in Aqueous and Organic Media. Stereochemistry and Competition Studies

  摘要：

  A systematic investigation of the stereoselectivity associated with coupling reactions involving the allylindium reagent-and 6-substituted 2-hydroxy-1-tetralones is presented. In each instance, the allylations were carried out in water, 50% aqueous THF, and dry THF. The extent of 1,2-induction was found to be highest-in THF-H2O (1:1) and to favor the trans diol isomer. Somewhat lower levels of stereochemical bias in the same direction were observed in pure water. However, further erosion of this trend was noted for those reactions performed in THF, such that a modest crossover in product distribution became apparent in certain examples. On the basis of competition experiments, both reaction trajectories give evidence of proceeding via chelated intermediates. The extent of stereoinduction was found to be in Line with the normal predilection of 2-cyclohexenones for axial attack, which is the process believed to be beset with minimal torsional effects. The substituents situated para to the ketone carbonyl do not exert a very large influence on product distribution, although electronic effects are evident in the context of the competition studies. A mechanistic model which integrates these findings is offered.

  DOI：

  10.1021/jo980825f

文献信息

• Melanin concentrating hormone antagonist
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US07115750B1

  公开（公告）日：2006-10-03

  A melanin-concentrating hormone antagonist which comprises a compound of the formula: wherein Ar1 is a cyclic group which may have substituents; X is a spacer having a main chain of 1 to 6 atoms; Y is a bond or a spacer having a main chain of 1 to 6 atoms; Ar is a monocyclic aromatic ring which may be condensed with a 4 to 8 membered non-aromatic ring, and may have further substituents; R1 and R2 are independently hydrogen atom or a hydrocarbon group which may have substituents; R1 and R2, together with the adjacent nitrogen atom, may form a nitrogen-containing hetero ring which may have substituents; R2 may form a spiro ring together with Ar; or R2, together with the adjacent nitrogen atom and Y, may form a nitrogen-containing hetero ring which may have substituents; or a salt thereof; which is useful as an agent for preventing or treating obesity, etc.

  一种黑色素浓集激素拮抗剂，包括以下化合物：其中Ar1是一个环状基团，可以有取代基；X是具有1至6个原子的主链间隔物；Y是一个键或具有1至6个原子的主链间隔物；Ar是一个单环芳香环，可以与4至8个成员的非芳香环融合，并且可以有进一步的取代基；R1和R2分别是氢原子或一个可以有取代基的碳氢基团；R1和R2与相邻的氮原子一起可以形成一个含氮杂环，该杂环可以有取代基；R2可以与Ar一起形成螺环；或者R2、相邻的氮原子和Y一起可以形成一个含氮杂环，该杂环可以有取代基；或其盐；它是用于预防或治疗肥胖等的药剂。
• MELANIN CONCENTRATING HORMONE ANTAGONIST
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1218336A2

  公开（公告）日：2002-07-03
• US7115750B1
  申请人：——

  公开号：US7115750B1

  公开（公告）日：2006-10-03
• [EN] MELANIN CONCENTRATING HORMONE ANTAGONIST<br/>[FR] ANTAGONISTE DE L'HORMONE DE CONCENTRATION DE LA MELANINE
  申请人：TAKEDA CHEMICAL INDUSTRIES LTD

  公开号：WO2001021577A2

  公开（公告）日：2001-03-29

  A melanin-concentrating hormone antagonist which comprises a compound of formula (I) wherein Ar1 is a cyclic group which may have substituents; X is a spacer having a main chain of 1 to 6 atoms; Y is a bond or a spacer having a main chain of 1 to 6 atoms; Ar is a monocyclic aromatic ring which may be condensed with a 4 to 8 membered non-aromatic ring, and may have further substituents; R?1 and R2¿ are independently hydrogen atom or a hydrocarbon group which may have substituents; R?1 and R2¿, together with the adjacent nitrogen atom, may form a nitrogen-containing hetero ring which may have substituents; R2 may form a spiro ring together with Ar; or R2, together with the adjacent nitrogen atom and Y, may form a nitrogen-containing hetero ring which may have substituents; or a salt thereof; which is useful as an agent for preventing or treating obesity, etc.
• Allylindation of 6-Substituted 2-Hydroxy-1-tetralones in Aqueous and Organic Media. Stereochemistry and Competition Studies
  作者：Paul C. Lobben、Leo A. Paquette

  DOI：10.1021/jo980825f

  日期：1998.10.1

  A systematic investigation of the stereoselectivity associated with coupling reactions involving the allylindium reagent-and 6-substituted 2-hydroxy-1-tetralones is presented. In each instance, the allylations were carried out in water, 50% aqueous THF, and dry THF. The extent of 1,2-induction was found to be highest-in THF-H2O (1:1) and to favor the trans diol isomer. Somewhat lower levels of stereochemical bias in the same direction were observed in pure water. However, further erosion of this trend was noted for those reactions performed in THF, such that a modest crossover in product distribution became apparent in certain examples. On the basis of competition experiments, both reaction trajectories give evidence of proceeding via chelated intermediates. The extent of stereoinduction was found to be in Line with the normal predilection of 2-cyclohexenones for axial attack, which is the process believed to be beset with minimal torsional effects. The substituents situated para to the ketone carbonyl do not exert a very large influence on product distribution, although electronic effects are evident in the context of the competition studies. A mechanistic model which integrates these findings is offered.