3-(naphthalen-2-yl)-2-(trimethylsilyl)propanoic acid | 345217-79-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(naphthalen-2-yl)-2-(trimethylsilyl)propanoic acid
• 英文别名: 3-Naphthalen-2-yl-2-trimethylsilanyl-propionic acid；3-Naphthalen-2-yl-2-trimethylsilylpropanoic acid；3-naphthalen-2-yl-2-trimethylsilylpropanoic acid
• CAS: 345217-79-0
• 化学式: C₁₆H₂₀O₂Si
• 分子量: 272.419
• InChiKey: KZGFIQAGYODOQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(naphthalen-2-yl)-2-(trimethylsilyl)propanoic acid 在 草酰氯 、 溴 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-Bromo-3-naphthalen-2-yl-2-trimethylsilanyl-propionyl chloride
  参考文献：
  名称：

  The highly enantioselective transformation of silylketenes into α-silylthioesters catalysed by cinchona alkaloids

  摘要：

  The reaction of silylketenes with thiophenol, mediated by cinchona alkaloid catalysts, proceeds to give alpha -silylthioester products in good chemical yield and with enantiomeric excess values in the range 79-93%. The absolute configuration of one of the thioester products was determined by X-ray diffraction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00304-5
• 作为产物：
  描述：

  (三甲基甲硅烷基）乙酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 lithium diisopropyl amide 作用下， 以88%的产率得到3-(naphthalen-2-yl)-2-(trimethylsilyl)propanoic acid
  参考文献：
  名称：

  The highly enantioselective transformation of silylketenes into α-silylthioesters catalysed by cinchona alkaloids

  摘要：

  The reaction of silylketenes with thiophenol, mediated by cinchona alkaloid catalysts, proceeds to give alpha -silylthioester products in good chemical yield and with enantiomeric excess values in the range 79-93%. The absolute configuration of one of the thioester products was determined by X-ray diffraction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00304-5

文献信息

• A Desilylative Approach to Alkyl Substituted C(1)‐Ammonium Enolates: Application in Enantioselective [2+2] Cycloadditions
  作者：Yihong Wang、Claire M. Young、Honglei Liu、Will C. Hartley、Max Wienhold、David. B. Cordes、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1002/anie.202208800

  日期：2022.9.19

  The catalytic generation of unsubstituted and alkyl substituted C(1)-ammonium enolates from α-silyl-α-alkyl substituted carboxylic acids using the isothiourea HyperBTM has been developed and applied in enantioselective [2+2]-cycloaddition reactions.

  使用异硫脲 HyperBTM 从 α-甲硅烷基-α-烷基取代的羧酸催化生成未取代和烷基取代的 C(1)-烯醇化铵已被开发并应用于对映选择性 [2+2]-环加成反应。
• Probing Regio- and Enantioselectivity in the Formal [2 + 2] Cycloaddition of C(1)-Alkyl Ammonium Enolates with β- and α,β-Substituted Trifluoromethylenones
  作者：Yihong Wang、Claire M. Young、David B. Cordes、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1021/acs.joc.2c02688

  日期：2023.6.16

  on both reaction components. Solely [2 + 2] cycloaddition products are observed when using α,β-substituted trifluoromethylenones or α-trialkylsilyl acetic acid derivatives; both [2 + 2] and [4 + 2] cycloaddition products are observed when using β-substituted trifluoromethylenones and α-alkyl-α-trialkylsilyl acetic acids as reactants, with the [2 + 2] cycloaddition as the major reaction product. The beneficial

  已开发出异硫脲催化的 C(1)-烷基和 C(1)-未取代的烯醇铵与 β- 和 α,β-取代的三氟亚甲基酮的区域和对映选择性形式 [2 + 2] 环加成反应。在所有情况下，观察到[2 + 2]-环加成优先于替代的[4 + 2]-环加成，使β-内酯具有优异的非对映选择性和对映选择性（34个例子，高达>95:5 dr，>99： 1 呃）。该过程的区域选择性取决于两种反应组分上取代基的性质。当使用α,β-取代的三氟亚甲基酮或α-三烷基甲硅烷基乙酸衍生物时，仅观察到[2+2]环加成产物；当使用β-取代的三氟亚甲基酮和α-烷基-α-三烷基甲硅烷基乙酸作为反应物时，观察到[2+2]和[4+2]环加成产物，以[2+2]环加成作为主要反应产物。该方案中酸组分内的 α-甲硅烷基取代基的有益作用已通过对照实验得到证明。
• The highly enantioselective transformation of silylketenes into α-silylthioesters catalysed by cinchona alkaloids
  作者：Alexander J Blake、Christopher L Friend、Robert J Outram、Nigel S Simpkins、Andrew J Whitehead

  DOI：10.1016/s0040-4039(01)00304-5

  日期：2001.4

  The reaction of silylketenes with thiophenol, mediated by cinchona alkaloid catalysts, proceeds to give alpha -silylthioester products in good chemical yield and with enantiomeric excess values in the range 79-93%. The absolute configuration of one of the thioester products was determined by X-ray diffraction. (C) 2001 Elsevier Science Ltd. All rights reserved.