1,2,3,4-tetrahydronaphthalene-carboxylic acid ethyl ester | 22743-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2,3,4-tetrahydronaphthalene-carboxylic acid ethyl ester
• 英文别名: ethyl 1,2,3,4-tetrahydro-2-naphthalene carboxylate；ethyl 2-tetralincarboxylate；1,2,3,4-tetrahydro-[2]naphthoic acid ethyl ester；1,2,3,4-Tetrahydro-[2]naphthoesaeure-aethylester；1,2,3,4-Tetrahydro-2-naphthoesaeure-ethylester；Ethyl 1,2,3,4-tetrahydronaphthalene-2-carboxylate
• CAS: 22743-31-3
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: YNWQBGTWCQVLSY-UHFFFAOYSA-N

物化性质

• 沸点：
  139-141 °C(Press: 10 Torr)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 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

• 作为反应物：
  描述：

  1,2,3,4-tetrahydronaphthalene-carboxylic acid ethyl ester 在 chromium(VI) oxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 丙酮 为溶剂， 生成 1,2,3,4-四氢萘-2-甲醛
  参考文献：
  名称：

  Julia,S. et al., Bulletin de la Societe Chimique de France, 1960, p. 84 - 91

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,4-四氢-2-萘甲酸 在 硫酸 作用下， 生成 1,2,3,4-tetrahydronaphthalene-carboxylic acid ethyl ester
  参考文献：
  名称：

  Sergiewskaja; Wolynskii, Zhurnal Obshchei Khimii, 1952, vol. 22, p. 321,324; engl. Ausg. S. 385, 387

  摘要：

  DOI：

文献信息

• 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。
• Reduction D′α,α′-dibromoorthoxylenes par les sels chromeux : generation facile d'orthoquino-dimethanes
  作者：D. Stephan、A. Gorgues、A. Le Coq

  DOI：10.1016/s0040-4039(01)91403-0

  日期：1984.1

  α,α′-Dibromoorthoxylenes undergo a very fast reductive elimination on treatment with chromous chloride, affording the reactive intermediate orthoquinodimethanes which evolve into spiroorthoxylylenes 2 or may be trapped with dienophiles (adducts 3 and 4). Some attempts in the field of anthracycline precursors are reported.

  用氯化亚铬处理后，α，α'-二溴邻二甲苯会经历非常快速的还原消除反应，从而提供反应性中间体邻醌二甲烷，这些中间体会演变成螺二甲撑二甲苯2或被二烯亲二烯捕获（加合物3和4）。报道了蒽环类前体领域的一些尝试。
• <i>o</i>-Quinodimethane Generation from α,α′-Dihalo-<i>o</i>-xylenes by Use of Sodium Benzenetellurolate
  作者：Nobuaki Kambe、Takashi Tsukamoto、Noritaka Miyoshi、Shinji Murai、Noboru Sonoda

  DOI：10.1246/bcsj.59.3013

  日期：1986.10

  benzenetellurolate anion to afford α,α′-bis(phenyltelluro)-o-xylene, which did not give o-quinodimethane under identical conditions. It is likely that the reaction proceeds through nucleophilic attack of benzenetellurolate anion at the tellurium atom of α-halo-α′-phenyltelluro-o-xylene which is formed in situ by the substitution of one of the halogen atoms of the starting α,α′-dihalo-o-xylene with the benzenetellurolate

  用苯碲酸钠处理 α,α'-二卤代-邻二甲苯得到邻醌二甲烷，它很容易与亲二烯体反应生成狄尔斯-阿尔德加合物。当反应在回流乙醇中使用 2 摩尔当量的苯碲酸盐对 α,α'-二卤代-邻二甲苯进行反应时，产率最高。该反应与卤原子与苯碲酸盐阴离子的取代竞争，得到 α,α'-双（苯基碲）-邻二甲苯，在相同条件下不会产生邻醌二甲烷。反应很可能是通过苯碲酸盐阴离子对α-卤代-α'-苯基碲-邻二甲苯的碲原子的亲核攻击进行的，α-卤代-α'-苯基碲-邻二甲苯是通过取代起始α，α的卤原子之一而原位形成'-二卤代-邻二甲苯与苯碲酸盐阴离子。
• Dehalogenation of o-dihalogen substituted arenes and α,α′-dihalogen substituted o-xylenes with lanthanum metal
  作者：Yutaka Nishiyama、Hiroshi Kawabata、Toshiki Nishino、Kouji Hashimoto、Noboru Sonoda

  DOI：10.1016/s0040-4020(03)01027-5

  日期：2003.8

  It was found that lanthanum metal caused the dehalogenation of o-dihalogen substituted arenes and alpha,alpha'-dihalogen substituted o-xylenes to generate the corresponding benzynes and o-quinodimethanes. When o-dihalogen substituted arenes were allowed to react with lanthanum metal in the presence of dienes, the Diels-Alder products between benzyne and dienes were formed in moderate to good yields. Similarly, the Diels-Alder adducts of o-quinodimethane with dienophiles were obtained, in the reaction of alpha,alpha'-dibromo-o-xylenes with lanthanum metal in the presence of dienophiles. (C) 2003 Elsevier Ltd. All rights reserved.
• STEPHAN, D.;GORGUES, A.;DE, COQ, A., TETRAHEDRON LETT., 1984, 25, N 49, 5649-5652
  作者：STEPHAN, D.、GORGUES, A.、DE, COQ, A.

  DOI：——

  日期：——