o-(allyldimethylsilyl)benzyl alcohol | 201050-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: o-(allyldimethylsilyl)benzyl alcohol
• 英文别名: (2-(hydroxymethyl)phenyl)dimethyl(2-propenyl)silane；[2-[Dimethyl(prop-2-enyl)silyl]phenyl]methanol
• CAS: 201050-01-3
• 化学式: C₁₂H₁₈OSi
• 分子量: 206.36
• InChiKey: GMSDMKMZVLDAEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  o-(allyldimethylsilyl)benzyl alcohol 在 叔丁基锂 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以70%的产率得到1,3-二氢-1,1-二甲基-2,1-苯并氧硅杂环戊二烯
  参考文献：
  名称：

  Alkoxides of o-silyl benzyl alcohols in cleavage reactions: approaches to benzyl and silyl anion equivalents

  摘要：

  o-硅基苄醇的烷氧基在温和条件下发生裂解反应，从而可以将苄基或硅基转移到亲电试剂。 反应3a [Formula: see text] 8，以及3c或4c [Formula: see text] 11展示了它们作为苄基和硅基阴离子当量的潜力。 关键词：硅迁移，苄基阴离子当量，硅基阴离子当量，β-硅基酮，γ-羟基硅烷。

  DOI：

  10.1139/v99-250
• 作为产物：
  描述：

  (2-Bromophenyl)methoxy-dimethyl-prop-2-enylsilane 在 lithium 作用下， 以 乙醚 为溶剂， 以90%的产率得到o-(allyldimethylsilyl)benzyl alcohol
  参考文献：
  名称：

  Intramolecular nucleophilic attack at silicon in o-silylbenzyl alcohols. Generation of allyl and benzyl anion equivalents

  摘要：

  Substituted silyl ethers of o-bromobenzyl alcohols and the derived o-silylbenzyl alcohols were used to transfer allyl and benzyl groups from silicon to the electrophiles benzaldehyde and benzophenone in excellent yields. gamma-Oxidosilane intermediates (and possibly hypercoordinated silicon intermediates) are postulated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.127

文献信息

• Silicon-Based Cross-Coupling Reagent and Production Method of Organic Compound Using the Same
  申请人：Nakao Yoshiaki

  公开号：US20090069577A1

  公开（公告）日：2009-03-12

  In one embodiment of the present invention, a silicon-based cross-coupling reagent is disclosed which is a highly stable tetraorganosilicon compound allowing for a cross-coupling reaction under mild reaction conditions without using fluoride ions, transition metal promoter, or strong bases, and the residue of the silicon reagent can be recovered and reused. The silicon-based cross-coupling reagent is a silicon compound in which an o-hydroxymethylphenyl group is connected to a silicon atom for intramolecular activation.

  在本发明的一个实施例中，揭示了一种基于硅的交叉偶联试剂，它是一种高度稳定的四有机硅化合物，允许在温和的反应条件下进行交叉偶联反应，而无需使用氟离子、过渡金属促进剂或强碱，并且可以回收和重复使用硅试剂的残留物。这种基于硅的交叉偶联试剂是一种硅化合物，其中一个 o-羟甲基苯基基团连接到硅原子以进行分子内活化。
• Intramolecular nucleophilic attack at silicon in o-silylbenzyl alcohols. Generation of allyl and benzyl anion equivalents
  作者：Paul F. Hudrlik、Anne M. Hudrlik、Yassin A. Jeilani

  DOI：10.1016/j.tet.2011.09.127

  日期：2011.12

  Substituted silyl ethers of o-bromobenzyl alcohols and the derived o-silylbenzyl alcohols were used to transfer allyl and benzyl groups from silicon to the electrophiles benzaldehyde and benzophenone in excellent yields. gamma-Oxidosilane intermediates (and possibly hypercoordinated silicon intermediates) are postulated. (C) 2011 Elsevier Ltd. All rights reserved.
• Alkoxides of <i>o</i>-silyl benzyl alcohols in cleavage reactions: approaches to benzyl and silyl anion equivalents
  作者：Paul F Hudrlik、Jose O Arango、Yousef M Hijji、Cosmas O Okoro、Anne M Hudrlik

  DOI：10.1139/v99-250

  日期：2000.11.1

  The alkoxides of o-silyl benzyl alcohols 4 undergo cleavage reactions under mild conditions allowing transfer of a benzyl or silyl group to an electrophile. Reactions 3a [Formula: see text] 8, and 3c or 4c [Formula: see text] 11 illustrate their potential as benzyl and silyl anion equivalents.Key words: silyl migration, benzyl anion equivalent, silyl anion equivalent, β-silyl ketone, γ-hydroxysilane.

  o-硅基苄醇的烷氧基在温和条件下发生裂解反应，从而可以将苄基或硅基转移到亲电试剂。 反应3a [Formula: see text] 8，以及3c或4c [Formula: see text] 11展示了它们作为苄基和硅基阴离子当量的潜力。 关键词：硅迁移，苄基阴离子当量，硅基阴离子当量，β-硅基酮，γ-羟基硅烷。