Dimethyl 2-prop-2-ynyl-2-(5-triethylsilylpenta-2,4-diynyl)propanedioate | 1231185-72-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Dimethyl 2-prop-2-ynyl-2-(5-triethylsilylpenta-2,4-diynyl)propanedioate
• 英文别名: dimethyl 2-prop-2-ynyl-2-(5-triethylsilylpenta-2,4-diynyl)propanedioate
• CAS: 1231185-72-0
• 化学式: C₁₉H₂₆O₄Si
• 分子量: 346.499
• InChiKey: SHRKDBXSMYVGDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Dimethyl 2-prop-2-ynyl-2-(5-triethylsilylpenta-2,4-diynyl)propanedioate 、 叔丁基二甲基烯丙基硅醚 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到dimethyl (Z)-5-(2-((tert-butyldimethylsilyl)oxy)ethylidene)-3-(4-(triethylsilyl)but-1-en-3-yn-2-yl)cyclohex-3-ene-1,1-dicarboxylate
  参考文献：
  名称：

  Initiation and Termination Mode of Enyne Cross-Metathesis and Metallotropic [1,3]-Shift Controlled by Remote Substituents

  摘要：

  The cross-metathesis of terminal alkyne and alkene using Ru-based Grubbs catalyst generally undergoes alpha-insertion. In this study, excellent control over alpha- and beta-insertion of ruthenium alkylidene into terminal alkynes has been achieved by using a substituent at a remote site from the reaction center. While the origin of this regioselectivity of insertion and metallotropic shift remains to be established, the trend indicates that the alpha-insertion with a concomitant metallotropic shift is favored with small substituents whereas the beta-insertion without a metallotropic shift is favored with bulky substituents such as tert-butyl and trialkyl silyl groups.

  DOI：

  10.1021/ja1020525

文献信息

• Initiation and Termination Mode of Enyne Cross-Metathesis and Metallotropic [1,3]-Shift Controlled by Remote Substituents
  作者：Sang Young Yun、Kung-Pern Wang、Mansuk Kim、Daesung Lee

  DOI：10.1021/ja1020525

  日期：2010.7.7

  The cross-metathesis of terminal alkyne and alkene using Ru-based Grubbs catalyst generally undergoes alpha-insertion. In this study, excellent control over alpha- and beta-insertion of ruthenium alkylidene into terminal alkynes has been achieved by using a substituent at a remote site from the reaction center. While the origin of this regioselectivity of insertion and metallotropic shift remains to be established, the trend indicates that the alpha-insertion with a concomitant metallotropic shift is favored with small substituents whereas the beta-insertion without a metallotropic shift is favored with bulky substituents such as tert-butyl and trialkyl silyl groups.