dimethyl trans(1,2),trans(2,3)-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-1,3,4-tetrahydronaphthalene-2,3-dicarboxylate | 82837-97-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: dimethyl trans(1,2),trans(2,3)-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-1,3,4-tetrahydronaphthalene-2,3-dicarboxylate
• 英文别名: dimethyl 6,7-dimethoxy-r-1-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-t-2,c-3-dicarboxylate；dimethyl (1S,2R,3R)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate
• CAS: 82837-97-6
• 化学式: C₂₄H₂₈O₈
• 分子量: 444.482
• InChiKey: XETWDUKWLBPUKH-XGRCMKMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl trans(1,2),trans(2,3)-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-1,3,4-tetrahydronaphthalene-2,3-dicarboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到r-1-(3,4-dimethoxyphenyl)-t-2,c-3-bis(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Asymmetric lignan synthesis. Isolariciresinol dimethyl ether

  摘要：

  DOI：

  10.1021/jo00368a018
• 作为产物：
  描述：

  1-(3,4-dimethoxyphenyl)-5,6-dimethoxy-1,3-dihydro-2-benzothiophene 在 过氧乙酸 作用下， 以 various solvent(s) 为溶剂， 反应 3.0h， 生成 dimethyl trans(1,2),trans(2,3)-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-1,3,4-tetrahydronaphthalene-2,3-dicarboxylate
  参考文献：
  名称：

  通过分子间环加成与醌二甲烷制备木脂素

  摘要：

  某些木脂素可以使用1-（芳基）-1,3-二氢-5,6-二烷氧基-苯并[ c ]噻吩2，2-二氧化物与亲二烯体之间的热反应作为关键步骤来制备。

  DOI：

  10.1039/c39820000430
• 作为试剂：
  描述：

  diethylzinc 、 苯甲醛 在 titanium(IV) isopropylate 、 dimethyl trans(1,2),trans(2,3)-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-1,3,4-tetrahydronaphthalene-2,3-dicarboxylate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 1-苯丙醇
  参考文献：
  名称：

  衍生自木脂酚羟基麦角甾醇的空间受阻手性1,4-二醇配体的合成和结构分析

  摘要：

  通过芳基四氢丁内酯木脂素（-）-分枝lin烯苷的芳基化/烷基化，将易于获得的天然木脂素羟基麦角甾醇转化为空间受阻的和光学纯的二苯基，二-2-萘基和四甲基1,4-二醇衍生物。此外，还详细研究了由高度取代的丁内酯形成的稳定半异构体的非对映选择性。通过分子力学（MM），Hartree-Fock（HF）/ 6-31G ∗和（DFT / B3LYP / TZVP）含量（包括熵贡献）和NMR光谱对计算所得的分子构象进行了计算研究。所采用的构象表明，这些新颖的手性1，4-二醇可能适合作为手性配体用于开发新的手性过渡金属和有机催化剂。

  DOI：

  10.1016/j.tetlet.2012.12.066

文献信息

• Non-oxidative dimerization of 3,4-dioxygenated cinnamates to aryltetralin lignans.
  作者：Bruno BOTTA、Paolo IACOMACCI、Vittorio VINCIGUERRA、Giuliano Delle MONACHE、Eszter GACS-BAITZ、Maurizio BOTTA、Domenico MISITI

  DOI：10.1248/cpb.38.3238

  日期：——

  The BF3 catalyzed dimerization of (E)-3, 4-dimethoxycinnamic acid methyl ester offers a route to aryltetralin lignans. The mechanism of the reaction is discussed.

  BF3催化的(E)-3, 4-二甲氧基肉桂酸甲酯二聚反应为芳基四氢木质素提供了一条途径。本文讨论了该反应的机理。
• Studies on Acidic Dimerization of 3,4-Dioxygenated Cinnamate or 1-Phenylpropene to Arylindane Lignans.
  作者：Yueh-Hsiung KUO、Chien-Huang WU、Rong-En WU、Sheng-Tsai LIN

  DOI：10.1248/cpb.43.1267

  日期：——

  The BF3-, TsOH- or HCOOH-catalyzed dimerization of 3, 4-dioxygenated cinnamate or 1-arylpropene offers a route to arylindane lignans. The structures of the products were elucidated and a mechanism is proposed for the reactions. The structures of the dimeric products assigned as aryltetralin lignans by Botta et al.

  在 BF3-、TsOH- 或 HCOOH 催化下，3，4-二氧代肉桂酸酯或 1-芳基丙烯发生了二聚反应，为获得芳基茚类木脂素提供了一条途径。阐明了产物的结构，并提出了反应的机理。Botta 等人将二聚产物的结构定为芳基四氢木质素。
• Erdtman, Justus Liebigs Annalen der Chemie, 1934, vol. 513, p. 229,237
  作者：Erdtman

  DOI：——

  日期：——
• Mann, John; Piper, Susan E.; Yeung, Lilan K.P., Journal of the Chemical Society. Perkin transactions I, 1984, p. 2081 - 2088
  作者：Mann, John、Piper, Susan E.、Yeung, Lilan K.P.

  DOI：——

  日期：——
• Slow Passage through a Saddle-Center Bifurcation
  作者：D. C. Diminnie、R. Haberman

  DOI：10.1007/s003329910009

  日期：2000.4

  Slowly varying conservative one-degree of freedom Hamiltonian systems are analyzed in the case of a saddle-center bifurcation. Away from unperturbed homoclinic orbits, strongly nonlinear oscillations are obtained using the method of averaging. A long sequence of nearly homoclinic orbits is matched to the strongly nonlinear oscillations before and after the slow passage. Usually solutions pass through the separatrix associated with the double homoclinic orbit before the saddle-center bifurcation occurs. For the case of slow passage through the special homoclinic orbit associated with a saddle-center bifurcation, solutions consist of a large sequence of nearly saddle-center homoclinic orbits connecting autonomous nonlinear saddle approaches, and the change in the action is computed. However, if the energy at one specific saddle approach is particularly small, then that one nonlinear saddle approach instead satisfies the nonautonomous first Painleve transcendent, in which case the solution usually either passes through the saddle-center homoclinic orbit in nearly the same way or makes a transition backwards in time to small oscillations around the stable center (though it is possible that the solution approaches the unstable saddle).