1,3-bis<(trimethylsilyl)oxy>-1-methoxy-2-methylbuta-1,3-diene | 148902-53-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1,3-bis<(trimethylsilyl)oxy>-1-methoxy-2-methylbuta-1,3-diene
• 英文别名: [(1Z)-1-methoxy-2-methyl-3-trimethylsilyloxybuta-1,3-dienoxy]-trimethylsilane
• CAS: 148902-53-8
• 化学式: C₁₂H₂₆O₃Si₂
• 分子量: 274.508
• InChiKey: SHQBVFSWQKHIJH-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-bis<(trimethylsilyl)oxy>-1-methoxy-2-methylbuta-1,3-diene 以90%的产率得到
  参考文献：
  名称：

  ANDERSON, G.;CAMERON, D. W.;FEUTRILL, G. I.;READ, R. W., TETRAHEDRON LETT., 1981, 22, N 43, 4347-4348

  摘要：

  DOI：

文献信息

• Towards the synthesis of streptovaricin D: Synthesis of fully elaborated aromatic precursors and coupling with ansa chain fragments
  作者：William R. Roush、David J. Madar

  DOI：10.1016/0040-4039(93)85004-g

  日期：1993.3

  The highly functionalized streptovaricin-damavaricin D aromatic precursors 12 and 15 have been prepared and coupled with propionaldehyde or unsaturated aldehydes 16 and 18 via aryllithium intermediates to give 2, 3 and 19.

  高度官能化链菌素- damavaricin d芳香族前体12和15已经制备并与丙醛或不饱和醛16和18通过芳基锂中间体，得到2，3和19。
• [3 + 4] and [3 + 5] Annulation Reactions of .alpha.-(Phenylthio)Dicarbonyl Electrophiles with Bis(trimethylsilyl) Enol Ethers: Synthesis of Highly Functionalized Medium Ring Carbocycles
  作者：Gary A. Molander、Paul R. Eastwood

  DOI：10.1021/jo00131a013

  日期：1995.12

  The [3 + 4] and [3 + 5] annulations of bis(trimethylsilyl) enol ethers with 1,4- and 1,5-dicarbonyl electrophiles bearing alpha-phenylthio substituents leads to the formation of bicyclic [3.2.1] and [3.3.1] ethers with good regiochemical and stereochemical control, Subsequent oxidation of the phenylthio moiety followed by reduction with SmI2 constitutes a high-yielding and regioselective process for cleavage of the bridging ether linkage. The overall strategy provides a synthetic pathway for the synthesis of highly functionalized medium ring carbocycles.
• Synthesis of specifically O-alkylated anthraquinones by cycloaddition
  作者：Donald W Cameron、Geoffrey I Feuitrill、Glenn B Gamble、John Stavrakis

  DOI：10.1016/s0040-4039(00)85117-5

  日期：1986.1
• Synthesis of highly functionalized naphthoate precursors to damavaricin D — Observation of kinetically stable benzocyclohexadienones in the bromination reactions of highly functionalized β-naphthol derivatives
  作者：William R. Roush、David J. Madar、D. Scott Coffey

  DOI：10.1139/cjc-79-11-1711

  日期：——

  Selective syntheses of the highly substituted bromonaphthoates 4a, 4b, 19, and 22 are reported. These compounds were targeted as precursors to the naphthoquinone nucleus of damavaricin D; compound 22 ultimately was used in the successful total synthesis. The synthesis of 22 features the Diels-Alder reaction of the oxygenated diene 5 and 2,6-dibromo-3-methylbenzoquinone 6 to establish the core naphthalenic unit. The quinone was protected throughout this synthesis as a 1,4-bis-methoxymethyl-1,4-dihydroquinone (see 36). The C-2-carboalkoxy group of 22 was added by carboxylation of the aryllithium intermediate generated from 36, and protected as a beta -trimethylsilylethyl ester. Finally, the C-8-Br substituent was introduced by NBS bromination of 38. This reaction proceeds by way of bromobenzocyclohexadienone 39. Related bromobenzo-cyclohexadienones 13 and 29 were observed in the NBS brominations of the highly functionalized beta -naphthyl MOM ethers 11 and 28. The bromobenzocyclohexadienones 29 and 39 undergo facile substitution reactions with chloride ion and reduction with bromide ion at rates competitive with base-promoted aromatization. The surprising kinetic stability of these intermediates is attributed to a combination of steric and stereoelectronic factors.
• Dichloro quinones as dienophiles: synthesis of alizarin derivatives
  作者：Donald W. Cameron、Geoffrey I. Feutrill、Philip L.C. Keep

  DOI：10.1016/s0040-4039(01)93478-1

  日期：——