methyl (2S*,3S*)-3-methyl-1,2,3,4-tetrahydronaphthalene-2-carboxylate | 86328-92-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl (2S*,3S*)-3-methyl-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• 英文别名: methyl (2SR,3SR)-3-methyl-1,2,3,4-tetrahydronaphthalene-2-carboxylate；methyl trans-3-methyl-1,2,3,4-tetrahydronaphthalene-2-carboxylate；trans-2-carbomethoxy-3-methyl-1,2,3,4-tetrahydronaphthalene；2-carbomethoxy-3-methyl-1,2,3,4-tetrahydronaphthalene；methyl (2R,3R)-3-methyl-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• CAS: 86328-92-9；112041-94-8
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: PSDFXEVSONRHNU-BXKDBHETSA-N

物化性质

• 沸点：
  288.1±19.0 °C(Predicted)
• 密度：
  1.053±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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 (2S*,3S*)-3-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。
• 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。
• Utilization of Me3SiSnBu3 in organic synthesis. Generation of o-quinodimethane from α,α′-dibromo-o-xylene and Me3SiSnBu3-CsF
  作者：Hiroki Sato、Naohiro Isono、Kimio Okamura、Tadamasa Date、Miwako Mori

  DOI：10.1016/s0040-4039(00)73042-5

  日期：1994.3

  The reaction of α,α′-dibromo-o-xylene with stannyl anion generated from Me3SiSnBu3 and CsF or TASF [(Et2N)3S+SiMe3F2−] in the presence of dienophiles afforded the [4+2] cyclization products in good to moderate yields.

  α的反应，α'二溴ö二甲苯与甲锡阴离子选自Me产生3 SiSnBu 3和CsF或TASF [（ET 2 N）3小号+森达3 ˚F 2 - ]在得到的亲二烯体的存在下，[4 +2]环化产物，产率中等至中等。
• Palladium-Catalyzed Formal [4+2] Cycloaddtion of <i>o</i>-Xylylenes with Olefins
  作者：Ryoichi Kuwano、Takenori Shige

  DOI：10.1021/ja070012l

  日期：2007.4.1

  o-(Silylmethyl)benzylic carbonates reacted with various conjugated olefins in the presence of the palladium catalyst, which was generated in situ from Pd(eta(3)-C3H5)Cp and 1,2-bis(diphenylphosphino)ethane (DPPE). The reaction provided 2- and/or 3-substituted tetralins in good yield. The catalytic reaction described here is equivalent to the [4+2] cycloaddition of o-xylylenes with dienophiles.