1-phenyl-1-trimethylsilyl-2-(prop-2'-yl)-3-methyl-silacyclohex-4-ene

• 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-phenyl-1-trimethylsilyl-2-(prop-2'-yl)-3-methyl-silacyclohex-4-ene
• 英文别名: 1-phenyl-1-trimethylsilyl-2-(prop-2'-yl)-3-methylsilacyclohex-4-ene；trimethyl-(3-methyl-1-phenyl-2-propan-2-yl-3,6-dihydro-2H-silin-1-yl)silane
• 化学式: C₁₈H₃₀Si₂
• 分子量: 302.607
• InChiKey: YFTUFMFBRPLITN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-phenyl-1-trimethylsilyl-2-(prop-2'-yl)-3-methyl-silacyclohex-4-ene 在 palladium on activated charcoal 氢气 、 boron trifluoride diacetate 、 potassium fluoride 、 双氧水 、 potassium hydrogencarbonate 作用下， 以 甲苯 、 氯仿 、 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 生成 4,6-dimethylheptane-1,5-diol
  参考文献：
  名称：

  Silenes as novel synthetic reagents: synthesis of diols and lactones from simple alkyldienes

  摘要：

  Aryl substituted silenes can be generated by a modified Peterson olefination reaction and trapped in situ to afford silacycles with high diastereoselectivity. These silacycles can be elaborated by 'Fleming-Tamao' type oxidation to provide access to functionalized diols and lactones. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.056
• 作为产物：
  描述：

  tris(trimethylsilyl)phenylsilane 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 25.0h， 生成 1-phenyl-1-trimethylsilyl-2-(prop-2'-yl)-3-methyl-silacyclohex-4-ene
  参考文献：
  名称：

  Silenes as novel synthetic reagents: synthesis of diols and lactones from simple alkyldienes

  摘要：

  Aryl substituted silenes can be generated by a modified Peterson olefination reaction and trapped in situ to afford silacycles with high diastereoselectivity. These silacycles can be elaborated by 'Fleming-Tamao' type oxidation to provide access to functionalized diols and lactones. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.056

文献信息

• Silenes as novel synthetic reagents: identification of a practical method for silene generation and trapping
  作者：Malcolm B. Berry、Russell J. Griffiths、Mahesh J. Sanganee、Patrick G. Steel、Daniel K. Whelligan

  DOI：10.1039/b404166f

  日期：——

  The elucidation of a robust and reliable sequence for the generation of highly reactive transient silenes from simple aldehydes is described. The key step involves a silyl-modified Peterson olefination which critically depends on the presence of a sub-stoichiometric amount of soluble lithium salts (LiBr).

  描述了一种从简单醛生成高度反应性瞬态硅烯的健全且可靠的序列阐明。关键步骤涉及硅基改性彼得森烯化，这在很大程度上依赖于存在亚化学计量的可溶性锂盐（LiBr）。
• Stereochemistry of the reaction of Si–phenyl silenes with butadienes: elaboration of the silacycloadducts to provide a novel route to substituted lactones
  作者：Mahesh J. Sanganee、Patrick G. Steel、Daniel K. Whelligan

  DOI：10.1039/b404175e

  日期：——

  silacycles accompanied by variable amounts of competing ene, [2 + 2] and silene dimer by-products. The silacycles are formed with good chemo- and stereo-selectivity and provide access to diols and lactones via a phenyl-triggered Fleming-Tamao oxidation.

  可以通过[4 + 2]环加成途径，通过一系列烷基丁二烯截留通过甲硅烷基修饰的Peterson烯烃化程序生成的硅，从而提供硅杂环化合物，并伴以不同量的竞争性烯，[2 + 2]和硅二聚体副产物。形成的silacycles具有良好的化学和立体选择性，并通过苯基触发的Fleming-Tamao氧化提供了与二醇和内酯的通道。
• Hosomi–Sakurai reactions of silacyclic allyl silanes
  作者：Jonathan D. Sellars、Patrick G. Steel、Michael J. Turner

  DOI：10.1039/b602642g

  日期：——

  Substituted silacyclohexenes, generated through silene-diene [4 + 2] cycloaddition reactions, undergo Lewis acid promoted Sakurai type reactions with acetals to afford, following oxidation of the resultant fluorosilane, 1,4-diols with four contiguous chiral centres.

  通过硅二烯-二烯[4 + 2]环加成反应生成的取代的硅环己烯，经过路易斯酸促进的樱井型与乙缩醛反应，在氧化所得的氟硅烷后，得到带有四个连续手性中心的1,4-二醇。
• Silenes in organic synthesis: a short synthesis of prelactone B
  作者：Jonathan D. Sellars、Patrick G. Steel

  DOI：10.1039/b608989e

  日期：——

  A sequence involving dihydroxylation and acid induced fragmentation of silene generated silacyclohexenes represents the key step in a concise synthetic route to β-hydroxy-δ-lactones.

  硅烯生成的硅环己烯的二羟基化和酸诱导碎裂过程是β-羟基-δ-内酯简明合成路线的关键步骤。
• Application of silacyclic allylsilanes to the synthesis of β-hydroxy-δ-lactones: synthesis of Prelactone B
  作者：Jonathan D. Sellars、Patrick G. Steel

  DOI：10.1016/j.tet.2009.01.116

  日期：2009.7

  Silacyclic allylsilanes generated through a silene-diene Diels-Alder cycloaddition represent versatile bifunctional reagents for organic synthesis. This is demonstrated in a short stereocontrolled synthesis of (+/-)-Prelactone B. (C) 2009 Elsevier Ltd. All rights reserved.