methyl 2-methyl-1,2,3,4-tetrahydronaphthalene-2-carboxylate | 117750-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 2-methyl-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• 英文别名: 2-carbomethoxy-2-methyl-1,2,3,4-tetrahydronaphthalene；methyl 2-methyl-3,4-dihydro-1H-naphthalene-2-carboxylate
• CAS: 117750-14-8
• 化学式: C₁₃H₁₆O₂
• mdl: MFCD20731141
• 分子量: 204.269
• InChiKey: XOYPOULSHGDOMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-[(trimethylsilyl)methyl]benzyl alcohol 在 potassium fluoride 、 18-冠醚-6 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 43.0h， 生成 methyl 2-methyl-1,2,3,4-tetrahydronaphthalene-2-carboxylate
  参考文献：
  名称：

  2-[(Trimethylsilyl)methyl]benzyl Methanesulfonates: Useful Precursors for the Generation of o-Quinodimethanes

  摘要：

  2-[(Trimethylsilyl)methyl]benzyl methanesulfonates react with potassium fluoride in the presence of a catalytic amount of 18-crown-6 at room temperature to give o-quinodimethanes, which are trapped with electron-deficient olefins to afford [4+2] cycloadducts in good yields.

  DOI：

  10.1055/s-0033-1341238

文献信息

• An Improvement of the Palladium-Catalyzed [4+2] Cycloaddition of o-(Silylmethyl)benzyl Carbonates with Alkenes
  作者：Ryoichi Kuwano、Yushu Jin、Kentaro Ishizuka

  DOI：10.1055/s-0034-1379014

  日期：——

  complex, which is generated in situ from Pd(η 3-C3H5)Cp and tris(4-methoxy-3,5-dimethylphenyl)phosphine, catalyzed the [4+2] cycloaddition of o-(silylmethyl)benzyl carbonates with alkenes. The reaction of the benzyl esters with methyl crotonate gave methyl 3-methyltetralin-2-carboxylate in 84% yield with 2% catalyst loading.

  钯配合物由 Pd(η 3-C3H5)Cp 和三（4-甲氧基-3,5-二甲基苯基）膦原位生成，催化邻（甲硅烷基甲基）苄基碳酸酯与烯烃。苄酯与巴豆酸甲酯的反应以84%的收率和2%的催化剂负载得到3-甲基四氢化萘-2-羧酸甲酯。
• Electro-organic reactions. Part 41. Diels-Alder reactions of o-quinodimethanes from the cathodic reduction of α, α′-dibromo-1,2-dialkylbenzenes
  作者：Erada Eru、Geoffrey E. Hawkes、James H.P. Utley、Peter B. Wyatt

  DOI：10.1016/0040-4020(95)00034-6

  日期：1995.3

  Cathodic reduction of α, α′-dibromo-1,2-dialkylbenzenes in DMF containing Et4N+ Br− as supporting electrolyte, in the presence of dienophiles (e.g. maleic anhydride derivatives), yielded Diels-Alder adducts of o-quinodimethanes. Selective reduction of the benzylic dibromides was often possible even when their irreversible cyclic voltammetric reduction peak potentials were more negative than the Eo

  阴极还原α，α'二溴-1,2-二烷基苯的DMF含有的Et 4 Ñ +溴-作为支持电解质，在亲二烯体的存在下（例如马来酸酐的衍生物），得到的狄尔斯-阿德耳加合物Ö -quinodimethanes。即使苄基二溴化物的不可逆环状伏安还原峰电位比酸酐的E o值更负，通常也可以选择性还原。这可能是氧化还原催化的结果，其中酸酐具有介体和亲二烯体的双重作用。
• 1,1-, 1,2-, and 1,4-eliminations from the corresponding dihalogenated compounds using Bu3SnSiMe3-F−
  作者：Hiroki Sato、Naohiro Isono、Irie Miyoshi、Miwako Mori

  DOI：10.1016/0040-4020(96)00376-6

  日期：1996.6

  1-, 1,2-, or 1,4- elimination of an aryl or vinyl halide with an appropriate leaving group at the α-, β-, or δ-position of halogen. Thus, alkylidene carbene 8 is generated from 1,1-dihalo-alkene 6 or 7 and benzyne 10 is generated from 1,2-dibromobenzene 9 and an o-quinodimethane 12 was produced from α,α′-dibromoxylene 11 a.

  在非常温和的条件下，在DMF中，在R 4 NX，CsF或TASF [（Et 2 N）3 SSiMe 3 F 2 ] 7存在下，由Me 3 SiSnBu 3（1）6生成的苯乙烯基阴离子2，用于8在卤素的α-，β-或δ位置带有适当离去基团的芳基或乙烯基卤化物的1,1-，1,2-或1,4-消除。因此，亚烷基卡宾8由1，1-二卤代烯烃6或7产生，而苯并炔10由1，2-二溴苯9产生。和ø -quinodimethane 12从α，α'-二溴二甲苯产生11一个。
• Reductive debromination of 1,2-bis(bromomethyl)arenes using tetrakis(dimethylamino)ethylene (TDAE)
  作者：Yutaka Nishiyama、Hiroshi Kawabata、Akihiro Kobayashi、Toshiki Nishino、Noboru Sonoda

  DOI：10.1016/j.tetlet.2004.11.114

  日期：2005.1

  A new method for the reductive debromination of 1,2-bis(bromomethyl)arenes has been developed. The treatment of 1,2-bis(bromomethyl)benzene with tetrakis(dimethylamino)ethylene (TDAE) (1) in the presence of olefins gave 1,2,3,4-tetrahydronaphthalenes in moderate to good yields.

  开发了一种新的还原方法，用于1,2-双（溴甲基）芳烃的还原脱溴。在烯烃存在下用四（二甲基氨基）乙烯（TDAE）（1）处理1，2-双（溴甲基）苯得到1,2,3,4-四氢萘，产率中等至良好。
• Cycloaddition of<i>o</i>-Quinodimethanes Generated from 1,2-Bis(bromomethyl)benzenes by Constant-Current Electroreduction
  作者：Naoki Kise、Ryosuke Mimura、Nasuo Ueda

  DOI：10.1246/bcsj.75.2693

  日期：2002.12

  The constant-current electroreduction of 1,2-bis(bromomethyl)benzenes with dienophiles in NH4NO3–MeOH gave Diels–Alder cycloadducts in moderate-to-good yields.

  在NH4NO3–MeOH中，1,2-二（溴甲基）苯与二烯亲体的恒电流电还原反应产生了中等至良好的Diels–Alder环加成产物。