ethyl 7-(triisopropylsilyloxy)-hept-2-ynoate | 1193381-02-0

• 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: ethyl 7-(triisopropylsilyloxy)-hept-2-ynoate
• 英文别名: ethyl 7-(triisopropylsilyloxy)hept-2-ynoate；Ethyl 7-tri(propan-2-yl)silyloxyhept-2-ynoate
• CAS: 1193381-02-0
• 化学式: C₁₈H₃₄O₃Si
• 分子量: 326.552
• InChiKey: IXUWJVYRWKQVFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 7-(triisopropylsilyloxy)-hept-2-ynoate 在 四丁基碘化铵 、 1,2-二氯乙烷 作用下， 反应 72.0h， 以43%的产率得到ethyl (2E)-3-chloro-2-iodo-7-(triisopropylsilyloxy)hept-2-enoate
  参考文献：
  名称：

  Single isomer trisubstituted olefins bearing alkyl groups

  摘要：

  E-beta-Chloro-alpha-iodo-alpha,beta-unsaturated esters were converted to single isomer trisubstituted olefins bearing alkyl substituents by using and alkyl-Suzuki cross coupling. The process was highly selective, and the products in all cases were isolated as single isomers. Mechanistic investigations indicated that this process transfers a hydrogen from water to the alpha-position of the substrate, and then an alkyl group is introduced to the beta-position of the intermediate template while replacing a chloride. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.09.002
• 作为产物：
  描述：

  氯甲酸乙酯 、 (hex-5-yn-1-yloxy)triisopropylsilane 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以72%的产率得到ethyl 7-(triisopropylsilyloxy)-hept-2-ynoate
  参考文献：
  名称：

  钯催化硼酸加成至炔基酯的开发：三取代烯烃作为单一异构体的合成

  摘要：

  非常小的膦配体可从炔基酯中获得单一异构体三取代的烯烃，同时完全控制立体化学和区域化学。该方法无需烯烃模板即可方便地合成单一异构体三取代的烯烃。

  DOI：

  10.1016/j.tet.2009.08.029

文献信息

• The Catalytic Addition of Alkyl Boranes to Alkynyl Esters Affording Single-Isomer Trisubstituted Olefins
  作者：William Ogilvie、Thivisha Rajagopal

  DOI：10.1055/s-0030-1259933

  日期：2011.5

  The generation of a series of trisubstituted olefins bearing alkyl substituents is described using a stereoselective and regio­selective addition to alkynyl esters. The method produces trisubstituted olefins as single isomers using a convenient and mild transformation in which alkyl boranes are cross-coupled with alkynyl esters and amides using palladium catalysis.

  描述了一种生成一系列具有烷基取代基的三取代烯烃的方法，该方法采用选择性立体和选择性区位的加成反应至炔基酯。这种方法通过方便温和的转化生成单一异构体的三取代烯烃，其中烷基硼烷与炔基酯和酰胺通过钯催化进行交叉偶联反应。
• Highly diastereoselective generation of various 3,3-disubstituted allyl boronates for the stereospecific construction of quaternary centers
  作者：Robyn Aryn Biggs、Maria Lambadaris、William W. Ogilvie

  DOI：10.1016/j.tetlet.2014.09.038

  日期：2014.10

  Single isomer trisubstituted olefins were converted into allyl boron nucleophiles that were condensed with aldehydes to give products containing quaternary centers. The products were obtained in extremely high diastereomeric ratios, a reflection of the stereochemical integrity of the starting materials. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.
• Single isomer trisubstituted olefins bearing alkyl groups
  作者：Thivisha Rajagopal、Alison B. Flynn、William W. Ogilvie

  DOI：10.1016/j.tet.2010.09.002

  日期：2010.11

  E-beta-Chloro-alpha-iodo-alpha,beta-unsaturated esters were converted to single isomer trisubstituted olefins bearing alkyl substituents by using and alkyl-Suzuki cross coupling. The process was highly selective, and the products in all cases were isolated as single isomers. Mechanistic investigations indicated that this process transfers a hydrogen from water to the alpha-position of the substrate, and then an alkyl group is introduced to the beta-position of the intermediate template while replacing a chloride. (C) 2010 Elsevier Ltd. All rights reserved.
• Development of a palladium catalyzed addition of boronic acids to alkynyl esters: synthesis of trisubstituted olefins as single isomers
  作者：Alexander Graham Bush、Jojo Liu Jiang、Philippa R. Payne、William W. Ogilvie

  DOI：10.1016/j.tet.2009.08.029

  日期：2009.10

  Very small phosphine ligands allow access to single isomer trisubstituted olefins from alkynyl esters with complete control of both stereochemistry and regiochemistry. This method provides a convenient synthesis of single isomer trisubstituted olefins without requiring olefin templates.

  非常小的膦配体可从炔基酯中获得单一异构体三取代的烯烃，同时完全控制立体化学和区域化学。该方法无需烯烃模板即可方便地合成单一异构体三取代的烯烃。