(Z)-3-(trimethylsilyl)-3-phenyl-2-propen-1-ol | 131674-12-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (Z)-3-(trimethylsilyl)-3-phenyl-2-propen-1-ol
• 英文别名: (Z)-3-phenyl-3-(trimethylsilyl)-2-propen-1-ol；(Z)-3-phenyl-3-(trimethylsilyl)prop-2-en-1-ol；(Z)-3-phenyl-3-(trimethylsilyl)prop-2-enol；(Z)-3-phenyl-3-trimethylsilylprop-2-en-1-ol
• CAS: 131674-12-9
• 化学式: C₁₂H₁₈OSi
• 分子量: 206.36
• InChiKey: NDNRYBJZFYKZBJ-XFXZXTDPSA-N

物化性质

• 沸点：
  292.8±19.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  14
• 可旋转键数：
  3
• 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：

  (Z)-3-(trimethylsilyl)-3-phenyl-2-propen-1-ol 在 C₂₆H₄₀IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以40%的产率得到(3R)-3-phenyl-3-trimethylsilylpropanal
  参考文献：
  名称：

  使用易于获得的第二代催化剂，伯烯丙基醇的铱催化的不对称异构化扩大了范围。

  摘要：

  第二代手性（P，N）-铱催化剂-易于从廉价的L-丝氨酸中获得-显示了伯烯丙基醇不对称异构化的扩展范围。

  DOI：

  10.1039/b920342g
• 作为产物：
  描述：

  (Z)-3-iodo-3-phenylprop-2-en-1-ol 在 叔丁基锂 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 (Z)-3-(trimethylsilyl)-3-phenyl-2-propen-1-ol
  参考文献：
  名称：

  （Z）-乙烯基硅烷烯丙基醇的新型立体选择性合成

  摘要：

  描述了一种用于合成（Z）-乙烯基硅烷烯丙基醇的高度立体选择性的新方法。这种用于这种γ-甲硅烷基化的烯丙基醇的方法采用了合适的甲硅烷基醚前体的新型1,4-0→sp 2 C甲硅烷基重排。

  DOI：

  10.1016/s0040-4039(00)97007-2

文献信息

• Improved Catalysts for the Iridium‐Catalyzed Asymmetric Isomerization of Primary Allylic Alcohols Based on Charton Analysis
  作者：Luca Mantilli、David Gérard、Sonya Torche、Céline Besnard、Clément Mazet

  DOI：10.1002/chem.201001311

  日期：2010.11.8

  improved generation of chiral cationic iridium catalysts for the asymmetric isomerization of primary allylic alcohols is disclosed. The design of these air‐stable complexes relied on the preliminary mechanistic information available, and on Charton analyses using two preceding generations of iridium catalysts developed for this highly challenging transformation. Sterically unbiased chiral aldehydes

  公开了用于伯烯丙基醇的不对称异构化的手性阳离子铱催化剂的改进的产生。这些空气稳定的配合物的设计依赖于可用的初步机理信息，并且依赖于Charton分析，Charton使用前两代为该极富挑战性的转化而开发的铱催化剂进行了分析。具有高水平的对映选择性，获得了以前无法获得的立体无偏手性醛，因此验证了有关所选配体设计元素的最初假设。还介绍了在大多数情况下实现高对映选择性的基本原理。
• Synthesis of Silicon Substituted Cyclopropylmethyl Alcohols in Optically Active Form<i>via</i>Asymmetric Simmons-Smith Reaction of γ-Silicon Substituted Allylic Alcohols
  作者：Yutaka Ukaji、Kazunori Sada、Katsuhiko Inomata

  DOI：10.1246/cl.1993.1227

  日期：1993.7

  Optically active silicon substituted cyclopropylmethyl alcohols were synthesized through asymmetric Simmons-Smith reaction; that is, the reaction of γ-silicon substituted allylic alcohols with diethylzinc and diiodomethane utilizing (+)-diethyl tartrate as a chiral auxiliary was found to afford the corresponding silicon substituted cyclopropylmethyl alcohols with high stereoselectivity up to 92% ee

  通过不对称Simmons-Smith反应合成了光学活性硅取代的环丙基甲醇；也就是说，发现γ-硅取代的烯丙醇与二乙基锌和二碘甲烷以酒石酸（+）-二乙酯作为手性助剂反应，得到相应的硅取代的环丙基甲醇，立体选择性高达92% ee。
• Copper(I) <i>tert</i>-Butoxide-Promoted 1,4 C^sp^²-to-O Silyl Migration:  Generation of Vinyl Copper Equivalents and Their Stereospecific Cross-Coupling with Allylic, Aryl, and Vinylic Halides
  作者：Haruhiko Taguchi、Kazushi Ghoroku、Makoto Tadaki、Akira Tsubouchi、Takeshi Takeda

  DOI：10.1021/jo025973r

  日期：2002.11.1

  copper(I) tert-butoxide and allylic halides followed by the tetrabutylammonium fluoride-assisted hydrolysis produced the allylation products, 2,5-alkadien-1-ols, with complete retention of configuration. Similar treatment of the organometallic intermediates with aryl and vinylic halides in the presence of palladium(0) catalyst gave the corresponding cross-coupling products in good yields. The stereoselective

  先用叔丁醇铜和烯丙基卤化物连续处理（Z）-γ-三甲基甲硅烷基烯丙基醇，再用四丁基氟化铵辅助水解，生成烯丙基化产物2,5-链二烯-1-醇，并完全保留配置。在钯（0）催化剂存在下，用芳基卤化物和乙烯基卤化物对有机金属中间体进行类似处理，从而以高收率得到相应的交叉偶联产物。还描述了原料的立体选择性制备。
• Stereoselective synthesis of terminal 1,3-butadienes by the condensation reaction of aldehydes and ketones with .gamma.-trimethylsilyl-substituted allylboranes
  作者：Kung K. Wang、Chin Liu、Yu Gui Gu、Friedrich N. Burnett、Prem D. Sattsangi

  DOI：10.1021/jo00005a045

  日期：1991.3

  Allylboranes 7-12, readily prepared from allenylsilanes 1-6 by hydroboration with 9-borabicyclo[3.3.1]nonane, smoothly condense with aldehydes and ketones to afford, after basic or acidic workup to promote the Peterson olefination reaction, a variety of terminal 1,3-butadienes. The dienes derived from aldehydes have high isomeric purity except in the cases with allylborane 12. Apparently, high diastereoselectivity was obtained during the condensation step with 7-11 to form 14. In each case, by simply changing the workup conditions to induce syn or anti elimination of hydroxytrimethylsilane, either the Z or the E isomer of the diene was obtained.
• Copper(I) <i>tert</i>-Butoxide-Promoted 1,4 C^s^p^²-to-O Silyl Migration:  Stereospecific Allylation of (<i>Z</i>)-γ-Trimethylsilyl Allylic Alcohols
  作者：Haruhiko Taguchi、Kazushi Ghoroku、Makoto Tadaki、Akira Tsubouchi、Takeshi Takeda

  DOI：10.1021/ol016837w

  日期：2001.11.1

  [GRAPHICS]The cyclic silyl ethers, 2,2-dimethyl-1-oxa-2-slia-3-cyclopentenes, were produced by the treatment of (2)-gamma -trimethylsilyl allylic alcohols with a catalytic or stoichiometric amount of lithium tort-butoxide. On the other hand, successive treatment of the alcohols with copper(l) tert-butoxide and allylic halides followed by the tetrabutylammmonium fluoride assisted hydrolysis produced the allylation products, 2,5-alkadien-1-ols, with complete retention of configuration of the double bond.