(1S,2R)-1-cyclohexyl-2-(dimethylphenyl)silylbut-3-ene-1-ol | 133285-27-5

• 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: (1S,2R)-1-cyclohexyl-2-(dimethylphenyl)silylbut-3-ene-1-ol
• 英文别名: (1S,2R)-1-cyclohexyl-2-(dimethyl(phenyl)silyl)but-3-en-1-ol；(1S,2R)-1-cyclohexyl-2-[dimethyl(phenyl)silyl]but-3-en-1-ol
• CAS: 133285-27-5
• 化学式: C₁₈H₂₈OSi
• 分子量: 288.505
• InChiKey: LUGPKCFONYILDX-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  烯丙基二甲基苯基硅烷 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 (1S,2R)-1-cyclohexyl-2-(dimethylphenyl)silylbut-3-ene-1-ol
  参考文献：
  名称：

  [(E)-γ-(Dimethylphenylsilyl)allyl]diisopinocampheylborane: a highly enantioselective reagent for the synthesis of anti-β-hydroxyallylsilanes

  摘要：

  anti-beta -Hydroxyallylsilanes are prepared with 88-95% e.e. via the asymmetric allylboration reactions of aldehydes and [(E)-gamma-(dimethylphenylsilyl)allyl]diisopinocampheylborane (7) (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01526-4

文献信息

• Synthesis of (+)-Bullatacin via the Highly Diastereoselective [3+2] Annulation Reaction of a Racemic Aldehyde and a Nonracemic Allylsilane
  作者：Jennifer M. Tinsley、Eric Mertz、Pek Y. Chong、Robert-André F. Rarig、William R. Roush

  DOI：10.1021/ol051719k

  日期：2005.9.1

  [reaction: see text] A total synthesis of (+)-bullatacin has been accomplished via a diastereoselective [3+2] annulation reaction of the highly enantiomerically enriched allylsilane 3 and racemic aldehyde 4, which provides the key bis-tetrahydrofuran fragment 15 with > or = 20:1 ds.

  [反应：参见文本]通过高度对映体富集的烯丙基硅烷3和外消旋醛4的非对映选择性[3 + 2]环合反应完成了（+）-bullacacin的全合成，该反应提供了关键的双-四氢呋喃片段15 >或= 20：1 ds。
• Diisopropyl tartrate modified (E)-γ-[(cyclohexyloxy)dimethylsilyl]- and (E)-γ-(dimethylphenylsilyl)allylboronates: Chiral Reagents for the Enantio- and Diastereoselective synthesis of anti 1,2-diols and 2-butene-1,4-diols via the formal α- and γ-hydroxyallylation of aldehydes
  作者：William R. Roush、Paul T. Grover

  DOI：10.1016/s0040-4020(01)88869-4

  日期：1992.1

  Enantioselective synthesis of 4-substituted (E)-2-butene-1,4-diols and anti 1,2-diols are described. Highly diastereoselective reactions of aldehydes and the chiral PhMe2Si- and (C6H11O)Me2Si- substituted allylboronates 25 and 26 provide anti homoallylic 29 and 50, respectively. Epoxidation of 29 with dimethyl dioxirane followed by acid catalyzed Petersen rearrangement of the intermediate epoxysilanols

  描述了4-取代的（E）-2-丁烯-1,4-二醇和抗1,2-二醇的对映选择性合成。醛与手性PhMe 2 Si-和（C 6 H 11 O）Me 2 Si-取代的烯丙基硼酸酯25和26的高度非对映选择性反应分别提供反均聚物29和50。29用二甲基二环氧乙烷环氧化，然后经酸催化的中间体环氧硅烷醇进行Petersen重排，可得到具有优异对映选择性（81-87％ee）的1,4-丁二醇27。Tamao氧化50提供抗二醇22（ee的64–72％）。这些程序尤其在与一系列氧化的手性醛进行双不对称反应时获得了优异的结果（图1和2）。这些方法有望用于非环状前体糖的非对映选择性合成中。
• Diisopropyl tartrate (E)-γ-(dimethylphenylsilyl)allylboronate, a chiral allylic alcohol β-carbanion equivalent for the enantioselective synthesis of 2-butene-1,4-diols from aldehydes
  作者：William R. Roush、Paul T. Grover

  DOI：10.1016/s0040-4039(00)97300-3

  日期：1990.1

  An enantioselective synthesis of 4-substituted (E)-2-buten-1,4-diols is described. The method involves the reaction of aldehydes with the chiral PhMe2Si- substituted allylboronate3 followed by epoxidation (dimethyl dioxirane) and acid catalyzed Petersen rearrangement of the intermediate epoxysilanols.

  描述了4-取代的（E）-2-丁烯-1,4-二醇的对映选择性合成。该方法涉及醛与手性PhMe 2 Si-取代的烯丙基硼酸酯3的反应，然后环氧化（二甲基二环氧乙烷）和酸催化的中间环氧硅烷醇的彼得森重排。
• Enantioselective Syntheses of <i>syn</i>- and <i>anti</i>-β-Hydroxyallylsilanes Via Allene Hydroboration-Aldehyde Allylboration Reactions
  作者：Ming Chen、William R. Roush

  DOI：10.1021/ol200392u

  日期：2011.4.15

  The kinetic hydroboration of allenylsilane 5 with ((d)Ipc)(2)BH at -40 degrees C provides allylborane 9Z with >= 12:1 selectivity. When the hydroboration is performed at temperatures above -40 degrees C, 9Z isomerizes to the thermodynamically more stable allylborane 9E with >20:1 selectivity. Subsequent treatment of 9Z or 9E with aldehydes at -78 degrees C provides syn- or anti-beta-hydroxyallylsilanes, 7 or 8, respectively.