2,6-diisopropylphenyl trimethylsilylglyoxylate | 852447-21-3

• 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: 2,6-diisopropylphenyl trimethylsilylglyoxylate
• 英文别名: [2,6-Di(propan-2-yl)phenyl] 2-oxo-2-trimethylsilylacetate
• CAS: 852447-21-3
• 化学式: C₁₇H₂₆O₃Si
• 分子量: 306.477
• InChiKey: NVDQUBCABLOFMH-UHFFFAOYSA-N

物化性质

• 沸点：
  354.6±52.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-diisopropylphenyl trimethylsilylglyoxylate 在 camphor-10-sulfonic acid 、 三乙胺 、 zinc(II) iodide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 12.0h， 生成 2,2-dimethyl-4-oct-1-ynyl-5-phenyl-[1,3]dioxolane-4-carboxylic acid 2,6-diisopropylphenyl ester
  参考文献：
  名称：

  Three-Component Coupling Reactions of Silylglyoxylates, Alkynes, and Aldehydes:  A Chemoselective One-Step Glycolate Aldol Construction

  摘要：

  A single-pot three-component coupling reaction of silylglyoxylates (1), terminal alkynes, and aldehydes in the presence of ZnI2 and Et3N is presented. The products of the reaction, densely functionalized silyl-protected glycolate aldols (2), can be converted to the corresponding acetonides (3) in a one-pot deprotection/ketalization sequence. A variety of terminal alkynes and aldehydes can be successfully employed to give a range of highly functionalized, fully protected 1,2-diols in good yields and moderate diastereoselectivities. Mechanistic experiments suggest that the zinc acetylide reacts with the silylgyloxylate (1) in a chemoselective manner. Using an unoptimized (+)-N-methylephedrine and Zn(OTf)2 system, silyl-deprotected adduct 2 was formed in 64% ee and 89:11 dr.

  DOI：

  10.1021/ja043884l
• 作为产物：
  描述：

  丙泊酚 在 Oxone 、 4-乙酰氨基苯磺酰叠氮 、 sodium acetate 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 30.25h， 生成 2,6-diisopropylphenyl trimethylsilylglyoxylate
  参考文献：
  名称：

  Three-Component Coupling Reactions of Silylglyoxylates, Alkynes, and Aldehydes:  A Chemoselective One-Step Glycolate Aldol Construction

  摘要：

  A single-pot three-component coupling reaction of silylglyoxylates (1), terminal alkynes, and aldehydes in the presence of ZnI2 and Et3N is presented. The products of the reaction, densely functionalized silyl-protected glycolate aldols (2), can be converted to the corresponding acetonides (3) in a one-pot deprotection/ketalization sequence. A variety of terminal alkynes and aldehydes can be successfully employed to give a range of highly functionalized, fully protected 1,2-diols in good yields and moderate diastereoselectivities. Mechanistic experiments suggest that the zinc acetylide reacts with the silylgyloxylate (1) in a chemoselective manner. Using an unoptimized (+)-N-methylephedrine and Zn(OTf)2 system, silyl-deprotected adduct 2 was formed in 64% ee and 89:11 dr.

  DOI：

  10.1021/ja043884l

文献信息

• Rhodium‐Catalyzed Asymmetric Arylation‐Induced Glycolate Aldol Additions of Silyl Glyoxylates
  作者：Nolan C. Turman、Kendrick L. Smith、Evan T. Crawford、Jacob G. Robins、Kathryn M. Weber、Shubin Liu、Jeffrey S. Johnson

  DOI：10.1002/anie.202311554

  日期：2023.10.16

  A chiral (diene)Rh(I) complex catalyzes the enantioselective three-component coupling reaction of silyl glyoxylates, boronic acids, and aldehydes to yield complex fully substituted mandelates. Notable features include the mild generation of chiral Rh-enolates by 1,2-Brook rearrangement and, from that point, modular preparation of glycolate aldol adducts.

  手性（二烯）Rh（I） 配合物催化乙醛酸甲硅烷酯、硼酸和醛的对映选择性三组分偶联反应，产生络合物完全取代的过德酸酯。显著特征包括通过 1,2-Brook 重排温和生成手性 Rh-烯醇酯，以及从那时起，乙醇酸羟醛醇加合物的模块化制备。
• TERT-BUTYL TERT-BUTYLDIMETHYLSILYLGLYOXYLATE: A USEFUL CONJUNCTIVE REAGENT
  作者：Nicewicz, David A.、Brétéché, Guillaume、Johnson, Jeffrey S.

  DOI：10.15227/orgsyn.085.0278

  日期：——