triethyl{(1R,2S)-1-[2-(4-methoxyphenoxy)ethyl]-2-methylbut-3-enyloxy}silane | 671798-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: triethyl{(1R,2S)-1-[2-(4-methoxyphenoxy)ethyl]-2-methylbut-3-enyloxy}silane
• 英文别名: triethyl-{1-[2-(4-methoxyphenoxy)ethyl]-2-methylbut-3-enyloxy}silane；triethyl-[(3R,4S)-1-(4-methoxyphenoxy)-4-methylhex-5-en-3-yl]oxysilane
• CAS: 671798-84-8
• 化学式: C₂₀H₃₄O₃Si
• 分子量: 350.574
• InChiKey: TUFLOOFZNHVTDD-FXAWDEMLSA-N

物化性质

• 沸点：
  410.3±40.0 °C(Predicted)
• 密度：
  0.938±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  triethyl{(1R,2S)-1-[2-(4-methoxyphenoxy)ethyl]-2-methylbut-3-enyloxy}silane 在 十二羰基三钌 正丁基锂 、 LiDBB 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 36.25h， 生成 (2R,3S,5S,6R,8S,9S)-8-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-[2-(4-methoxyphenoxy)ethyl]-3,5,9-trimethyl-1,7-dioxaspiro[5.5]undecane
  参考文献：
  名称：

  Synthesis of the C16−C35 Fragment of Integramycin Using Olefin Hydroesterification as a Linchpin Reaction

  摘要：

  The spiroketal unit of the HIV-integrase inhibitor integramycin has been prepared in an efficient and convergent manner. Key steps in this sequence include the use of ruthenium-mediated hydroesterification reactions of homoallylic alcohols and silyl ethers, and a C,O-dianionic addition into a lactone provides the spiroketal while minimizing protecting group manipulations.

  DOI：

  10.1021/ol036339i
• 作为产物：
  描述：

  1-(but-3-en-1-yloxy)-4-methoxybenzene 在 咪唑 、 三氯一茂钛 、 (4S,5S)-(2,2-二甲基-1,3-二氧戊环-4,5-二基)双(二苯基甲醇) 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 7.83h， 生成 triethyl{(1R,2S)-1-[2-(4-methoxyphenoxy)ethyl]-2-methylbut-3-enyloxy}silane
  参考文献：
  名称：

  Synthesis of the C16−C35 Fragment of Integramycin Using Olefin Hydroesterification as a Linchpin Reaction

  摘要：

  The spiroketal unit of the HIV-integrase inhibitor integramycin has been prepared in an efficient and convergent manner. Key steps in this sequence include the use of ruthenium-mediated hydroesterification reactions of homoallylic alcohols and silyl ethers, and a C,O-dianionic addition into a lactone provides the spiroketal while minimizing protecting group manipulations.

  DOI：

  10.1021/ol036339i

文献信息

• Investigations of the Scope and Mechanism of the Tandem Hydroesterification/Lactonization Reaction
  作者：Lijun Wang、Paul E. Floreancig

  DOI：10.1021/ol048378f

  日期：2004.11.1

  alcohols and 2-pyridylmethyl formate in the presence of Ru(3)(CO)(12) initiates a tandem sequence of hydroesterification and lactonization. Mechanistic studies suggest that regioselectivity and overall reaction efficiency are governed by the relative rates of reductive elimination and beta-hydride elimination for the alkylruthenium intermediates.

  在Ru（3）（CO）（12）存在的情况下加热烯丙基和均烯丙基醇和甲酸2-吡啶基甲基甲酸酯可引发氢化酯化和内酯化的串联序列。机理研究表明，区域选择性和整体反应效率受烷基钌中间体的相对消除和β-氢化物消除的相对速率支配。
• Synthesis of the C16−C35 Fragment of Integramycin Using Olefin Hydroesterification as a Linchpin Reaction
  作者：Lijun Wang、Paul E. Floreancig

  DOI：10.1021/ol036339i

  日期：2004.2.1

  The spiroketal unit of the HIV-integrase inhibitor integramycin has been prepared in an efficient and convergent manner. Key steps in this sequence include the use of ruthenium-mediated hydroesterification reactions of homoallylic alcohols and silyl ethers, and a C,O-dianionic addition into a lactone provides the spiroketal while minimizing protecting group manipulations.