1-Phenyl-4-trimethylsilylbut-3-en-1-ol | 68724-62-9

• 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: 1-Phenyl-4-trimethylsilylbut-3-en-1-ol
• CAS: 68724-62-9
• 化学式: C₁₃H₂₀OSi
• 分子量: 220.387
• InChiKey: LQTQDLVBCHEBOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (trimethylsilyl)allyl (pinacolato)boronate 、 苯甲醛 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以46%的产率得到1-Phenyl-4-trimethylsilylbut-3-en-1-ol
  参考文献：
  名称：

  在新型路易斯和布朗斯台德酸催化的歧管下将官能化的α-取代的烯丙基硼酸酯加成至醛中

  摘要：

  在标准的热（未催化）条件和新型的路易斯和布朗斯台德酸催化的条件下，考察了向苯甲醛中添加四种模式α-取代的烯丙基硼酸酯到苯甲醛中的立体和化学选择性。使用Sc（OTf）3或三氟甲磺酸作为催化剂，α-乙基烯丙基硼酸酯1a会导致令人惊讶的立体选择性反转，可以通过未催化途径和催化途径之间的烯丙基硼化过渡态几何形状的细微差异来初步合理化。还发现α-甲硅烷基试剂的化学选择性（1c和1d可以在使用催化剂时逆转，从而提供烯丙基甲硅烷基化产物而不是由热未催化反应获得的烯丙基硼化产物。

  DOI：

  10.1016/j.tetlet.2005.10.115

文献信息

• The influence of (organo)metallics “metal-tuning” on stereo- and regio-chemical convergence in reactions of allylic carbanions with aldehydes
  作者：Yoshinori Yamamoto、Yoshikazu Saito、Kazuhiro Maruyama

  DOI：10.1016/0022-328x(85)80216-3

  日期：1985.9

  Although the reaction of heterosubstituted allylic carbanions (2) with aldehydes generally produces a mixture of the γ- and α-adducts (4 and 3), syn-3 and anti-3 can be prepared either exclusively or predominantly by the proper choice of the organometallic compound added.

  虽然杂取代碳负离子烯丙基（反应2）与醛通常产生γ-和α-加合物的混合物（4和3），顺式- 3和抗- 3既可以完全或主要由的适当选择制备添加有机金属化合物。
• Gallium-mediated highly regioselective reactions of trimethylsilylpropargyl bromide and trimethylsilylallyl bromide with carbonyl compounds
  作者：Ying Han、Yao-Zeng Huang

  DOI：10.1016/s0040-4039(00)78562-5

  日期：1994.12

  One-pot reactions of gallium powder, trimethylsilylpropargyl bromide, aldehydes or ketones in the presence of KI and LiCl show very high acetylenic selectivity and under the same conditions, trimethylsilylallyl bromide also exhibits very high selectivity favoring α-adducts.

  镓粉，三甲基甲硅烷基炔丙基溴，醛或酮在KI和LiCl存在下的一锅反应显示出很高的炔属选择性，在相同条件下，三甲基甲硅烷基烯丙基溴也表现出非常高的选择性，有利于α加合物。
• Stereocontrol using a heterosubstituted allylic carbanion. Regio- and stereo-selective reactions of trimethylsilyl allylic carbanions with aldehydes
  作者：Yoshinori Yamamoto、Yoshikazu Saito、Kazuhiro Maruyama

  DOI：10.1039/c3982001326b

  日期：——

  Regio- and stereo-selective coupling between trimethylsilyl allyl carbanions and aldehydes is achieved in the presence of an additive, ‘M’; use of R2BCl or EtAlCl2 as the additive gives the threo isomer (3) predominantly, while use of Bu3SnCl–BF3 affords the erythro isomer exclusively.

  在添加剂“ M”的存在下，实现了三甲基甲硅烷基烯丙基碳负离子与醛之间的区域和立体选择性偶联。使用R 2 BCl或EtAlCl 2作为添加剂主要产生苏式异构体（3），而使用Bu 3 SnCl–BF 3则仅提供赤型异构体。
• Regional convergence in the reaction of heterosubstituted allylic carbanions via allylic aluminum and boron ate complexes
  作者：Yoshinori Yamamoto、Hidetaka Yatagai、Yoshikazu Saito

  DOI：10.1021/jo00180a027

  日期：1984.3
• Preparation of γ-Heterosubstituted Allylindium and Diindium Reagents and Their Reactions with Carbonyl Compounds
  作者：Tsunehisa Hirashita、Toshiya Kamei、Tomoaki Horie、Hatsuo Yamamura、Masao Kawai、Shuki Araki

  DOI：10.1021/jo9816111

  日期：1999.1.1

  Various gamma-heteroatom-substituted allylindium reagents were prepared, and their reactions with carbonyl compounds were examined. The reaction of 1,3-dibromopropene with metallic indium gave two types of organoindium species, gamma-bromoallylindium and allylic diindium reagents. While the former gave 2-phenyl-3-vinyloxirane upon the coupling with benzaldehyde, the latter gave 1-phenylbut-3-en-1-o1. 1-Iodo-3-bromopropene gave the homoallylic alcohol exclusively. gamma-Alkoxyallylindium reagents were prepared by treating the corresponding gamma-alkoxyallyllithium with indium trichloride and reacted with benzaldehyde to give vic-diol mono ethers in high yields with good syn selectivity. gamma-(Trimethylsilyl)allylindium and alpha,gamma-disubstituted allylindium reagents were also prepared via transmetalation with the corresponding allyllithium.