(Z)-3-phenyl-2-(trimethylsilyl)prop-2-en-1-ol | 97537-58-1

• 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: (Z)-3-phenyl-2-(trimethylsilyl)prop-2-en-1-ol
• CAS: 97537-58-1
• 化学式: C₁₂H₁₈OSi
• 分子量: 206.36
• InChiKey: IXYCUBPDMLJTLB-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-phenyl-2-(trimethylsilyl)prop-2-en-1-ol 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.5h， 生成 3-苯丙酸甲酯
  参考文献：
  名称：

  Generation and trapping of allene oxides: An approach to chiral, nonracemic α-alkoxyketones

  摘要：

  Epoxy mesylates 5 react with a variety of sodium alkoxides to produce the corresponding alpha-alkoxyketones in good yields. Evidence is presented for the involvement of transient allene oxides in these reactions. Enantiomerically enriched epoxy mesylates (2R,3S)-5a-c were prepared using the Sharpless asymmetric epoxidation reaction as the key step. These precursors rearrange to alpha-alkoxyketones without significant racemisation under modified reaction conditions (ROK, 18-crown-6, THF, -78 degrees C). The reactions are shown to proceed with stereochemical inversion at the epoxide centre. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00878-3
• 作为产物：
  描述：

  苯基乙炔基三甲基硅烷 在 甲基锂 、 二异丁基氢化铝 作用下， 以 乙醚 为溶剂， 生成 (Z)-3-phenyl-2-(trimethylsilyl)prop-2-en-1-ol
  参考文献：
  名称：

  Preparation of methylenedifluorocyclopropanes via cyclopropyl anion promoted β-elimination

  摘要：

  Preparation of methylenedifluorocyclopropanes 2 through the beta-elimination reaction promoted by difluorocyclopropyl anion formed by cleavage of C-Si bond with TBAF is described. Base-catalyzed isomerization of 2 to difluorocyclopropene 11 shows the latter structure thermodynamically more stable in contrast to non-fluorinated cases. Application of this method to the synthesis of methylenedifluorocyclopropylglycine (F(2)MCPG) derivative 17 is also presented. (C) 1999 Elsevier Science Ltd. All rights resented.

  DOI：

  10.1016/s0040-4020(99)00588-8

文献信息

• Diversity-Oriented Stereoselective Synthesis of β,γ-Disubstituted <i>tert</i>-Homoallylic Alcohols
  作者：Takeshi Takeda、Sota Amarume、Ippei Sekioka、Akira Tsubouchi

  DOI：10.1021/acs.orglett.5b00084

  日期：2015.3.6

  The successive treatment of beta-(trimethylsilyl)allyl phenyl sulfides with titanocene(II)-1-butene complex and ketones produced tertiary gamma-(trimethylsilyl)homoallylic alcohols with good anti-selectivity, which reacted with a variety of organic halides in the presence of copper(I) tert-butoxide to afford the cross-coupling products, gamma-substituted homoallylic alcohols.