trans-1,1-dicarbomethoxy-4-methyl-3-[(trimethylsilyl)methyl]cyclopentane

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-1,1-dicarbomethoxy-4-methyl-3-[(trimethylsilyl)methyl]cyclopentane
• 英文别名: dimethyl trans-4-methyl-3-[(trimethylsilyl)methyl]cyclopentane-1,1-dicarboxylate
• 化学式: C₁₄H₂₆O₄Si
• 分子量: 286.444
• InChiKey: WRAUMAIEIRYGIJ-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  三甲基硅烷 、 二烯丙基丙二酸二甲酯 在 <(phen)PdCH3(Et2O)>^+- 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以80%的产率得到trans-1,1-dicarbomethoxy-4-methyl-3-[(trimethylsilyl)methyl]cyclopentane
  参考文献：
  名称：

  Tandem Cyclization/Hydrosilylation of Functionalized 1,6-Dienes Catalyzed by a Cationic Palladium Complex

  摘要：

  DOI：

  10.1021/ja980242n

文献信息

• Tris(trimethylsilyl)silyl Radical Induced Bicyclization of 1,6-Dienes and 1,6-Enynes Providing 3,3-Bis(trimethylsilyl)-3-silabicyclo[3.3.0]octanes and 3-Silabicyclo[3.3.0]oct-1-enes
  作者：Katsukiyo Miura、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1246/bcsj.66.2348

  日期：1993.8

  Treatment of 1,6-dienes with tris(trimethylsilyl)silane in the presence of Et3B or α,α′-azobis(isobutyronitrile) afforded 3,3-bis(trimethylsilyl)-3-silabicyclo[3.3.0]octanes in addition to monocyclized cyclopentanes. Bicyclization of 1,6-enynes provided the corresponding 3-silabicyclo[3.3.0]oct-1-enes.

  在 Et3B 或 α,α′-偶氮二异丁腈存在下，用三(三甲基硅基)硅烷处理 1,6- 二烯，除了得到单环戊烷外，还得到了 3,3-双(三甲基硅基)-3-硅杂双环[3.3.0]辛烷。1,6-烯炔的双环化提供了相应的 3-硅杂双环[3.3.0]辛-1-烯。
• Cyclization/Hydrosilylation of Functionalized Dienes Catalyzed by a Cationic Palladium Phenanthroline Complex
  作者：Ross A. Widenhoefer、Carmine N. Stengone

  DOI：10.1021/jo9913006

  日期：1999.11.1

  Mixtures of(phen)PdMe2 (2a) and HBAr'(4) (3a) or (phen)PdMe(Cl) (2b) and NaBAr'(4) (3b) [phen = 1, 10-phenanthroline; Ar' = 3,5-C6H3(CF3)(2)] catalyzed the cyclization/hydrosilylation of functionalized 1,6-dienes to form silylated cyclopentanes in good yield and with excellent trans selectivity about the newly formed C-C bond (typically >50:1). A range of tertiary hydrosilanes were employed in the procedure although unhindered trialkylsilanes provided the most consistent results. The protocol tolerated a range of polar functionality including esters, ethers, amides, sulfones, and cyano groups. 4,4-Disubstitution on the diene backbone promoted cyclization, and a homoallylic ester, ketone, or ether directing group was required for efficient cyclization. The procedure tolerated dienes which possessed a single trans-substituted olefin and also tolerated allylic substitution. These substituted dienes underwent cyclization/hydrosilylation to form carbocycles resulting from transfer of the silyl group to the less hindered olefin. Mixtures of 2a and 3a also catalyzed the cyclization/hydrosilylation of functionalized 1,7-dienes to form silylated cyclohexane derivatives. Cyclization/hydrosilylation of 1,7-dienes was typically slower, less stereoselective, and more sensitive to substitution than was cyclization of 1,6-dienes.
• Tandem Cyclization/Hydrosilylation of Functionalized 1,6-Dienes Catalyzed by a Cationic Palladium Complex
  作者：Ross A. Widenhoefer、Michael A. DeCarli

  DOI：10.1021/ja980242n

  日期：1998.4.1