6,7-dimethoxy-1-tetralone oxime | 52401-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6,7-dimethoxy-1-tetralone oxime
• 英文别名: 6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one oxime；6,7-dimethoxytetralone oxime；6,7-dimethoxy-3,4-dihydro-2H-naphthalen-1-one oxime；6,7-Dimethoxy-3,4-dihydro-2H-naphthalin-1-on-oxim；N-(6,7-dimethoxy-3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamine
• CAS: 52401-41-9
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: PYZJFASRHCPXNX-UHFFFAOYSA-N

物化性质

• 熔点：
  157-158 °C
• 沸点：
  389.0±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-1-tetralone oxime 在 二异丁基氢化铝 、 sodium fluoride 作用下， 以 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 以38%的产率得到7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of brain penetrant benzazepine-based histone deacetylase 6 inhibitors for alleviating stroke-induced brain infarction

  摘要：

  DOI：

  10.1016/j.ejmech.2021.113383
• 作为产物：
  描述：

  4-(3,4-Dimethoxyphenyl)but-3-enoic acid 在 吡啶 、 palladium on activated charcoal 、 盐酸羟胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.17h， 生成 6,7-dimethoxy-1-tetralone oxime
  参考文献：
  名称：

  叔丁醇钾促进的有机催化直接联芳基偶联反应快速合成吡咯并菲啶酮，菲啶和苯并[ c ]菲啶

  摘要：

  在叔丁醇钾和有机分子作为催化剂存在的情况下，已经开发出一种涉及邻卤代N芳基苄胺的“无过渡金属”分子内联芳基偶合的方法。该反应似乎通过KO t Bu促进的分子内均溶芳族取代（HAS）进行。有趣的是，这种联芳基偶合在叔丁醇钾作为唯一促进剂的情况下也起作用。在进一步扩展我们的方法时，我们发现N-酰基2-溴-N-芳基苄胺经历了一锅N-脱保护/联芳基偶联，然后进行氧化，因此提供了通往菲啶和苯并[ c ]菲啶骨架的快速途径。该策略已被应用于简明的金莲花科生物碱的合成。oxoassoanine（1B），anhydrolycorinone（1D），5,6- dihydrobicolorine（2D），trispheridine（2B），和苯并[ C ^ ]菲啶生物碱dihydronitidine（图3b），dihydrochelerythidine（3D），dihydroavicine（3F），norni

  DOI：

  10.1021/jo400890k

文献信息

• Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid
  作者：Minmin Zhang、Shuowen Yu、Fangzhi Hu、Yijun Liao、Lihua Liao、Xiaoying Xu、Weicheng Yuan、Xiaomei Zhang

  DOI：10.1039/c6cc01200k

  日期：——

  Enantioselective [3+2] coupling of cyclic enamides with quinone monoimines was realised using a chiral phosphoric acid as a catalyst. This transformation allowed for the synthesis of highly enantioenriched polycyclic 2,3-dihydrobenzofurans...

  使用手性磷酸作为催化剂，实现环酰胺与醌单亚胺的对映选择性[3 + 2]偶联。该转化允许合成高度对映体富集的多环2,3-二氢苯并呋喃。
• Direct arylation of cyclic enamides via Pd(ii)-catalyzed C–H activation
  作者：Hai Zhou、Wan-Jun Chung、Yun-He Xu、Teck-Peng Loh

  DOI：10.1039/b903151k

  日期：——

  A new direct coupling of cyclic enamides with aryl boronic acids viaPd(II)-catalyzed C–H functionalization has been achieved with good yields (up to 90%).

  通过钯（II）催化的 CâH 功能化，实现了环烯丙基酰胺与芳基硼酸的一种新的直接偶联，并取得了良好的收率（高达 90%）。
• Synthesis of hindered secondary amines via Grignard reagent addition to ketonitrones
  作者：Martin A. Schwartz、Xiufeng Hu

  DOI：10.1016/s0040-4039(00)91707-6

  日期：1992.3

  Grignard reagents add to ketonitrones in a nonpolar solvent to afford N,N-dialkylhydroxylamines in good yields and with little competing proton transfer. Deoxygenation of the crude hydroxylamines with carbon disulfide then completes an efficient general synthetic route to hindered sec-alkyl-tert-alkylamines and to di-tert-alkylamines.

  格氏试剂在非极性溶剂中加到酮硝酮中，以良好的收率和极少的质子转移竞争性获得N，N-二烷基羟胺。然后用二硫化碳对粗羟胺进行脱氧，从而完成了一条有效的通用合成路线，可生成受阻的仲烷基叔烷基胺和二叔烷基胺。
• The role of human and mouse Y chromosome genes in male infertility
  作者：Nabeel A. Affara、M. J. Mitchell

  DOI：10.1007/bf03343787

  日期：2000.11

  It was suggested by Ronald Fisher in 1931 that genes involved in benefit to the male (including spermatogenesis genes) would accumulate on the Y chromosome. The analysis of mouse Y chromosome deletions and the discovery of microdeletions of the human Y chromosome associated with diverse defective spermatogenic phenotypes has revealed the presence of intervals containing one or more genes controlling male germ cell differentiation. These intervals have been mapped, cloned and examined in detail for functional genes. This review discusses the genes mapping to critical spermatogenesis intervals and the evidence indicating which are the most likely candidates underlying Y-linked male infertility. (C) 2000, Editrice Kurtis.
• Pd-Catalyzed Semmler–Wolff Reactions for the Conversion of Substituted Cyclohexenone Oximes to Primary Anilines
  作者：Wan Pyo Hong、Andrei V. Iosub、Shannon S. Stahl

  DOI：10.1021/ja4073172

  日期：2013.9.18

  Homogeneous Pd catalysts have been identified for the conversion of cyclohexenone and tetralone O-pivaloyl oximes to the corresponding primary anilines and 1-aminonaphthalenes. This method is inspired by the Semmler-Wolff reaction, a classic method that exhibits limited synthetic utility owing to its forcing conditions, narrow scope, and low product yields. The oxime N-O bond undergoes oxidative addition to Pd-0(PCy3)(2), and the product of this step has been characterized by X-ray crystallography and shown to undergo dehydrogenation to afford the aniline product.