5-(9-borabicyclo[3.3.1]nonan-9-yl)pentyl benzoate | 1038863-39-6

• 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: 5-(9-borabicyclo[3.3.1]nonan-9-yl)pentyl benzoate
• 英文别名: 5-(9-Borabicyclo[3.3.1]nonan-9-yl)pentyl benzoate
• CAS: 1038863-39-6
• 化学式: C₂₀H₂₉BO₂
• 分子量: 312.26
• InChiKey: ZAUZYJYEOHYWKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(9-borabicyclo[3.3.1]nonan-9-yl)pentyl benzoate 、 2-丁炔酸乙酯 在 三乙烯二胺 、 水 、 palladium diacetate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以90%的产率得到(6E)-8-ethoxy-6-methyl-8-oxooct-6-enyl benzoate
  参考文献：
  名称：

  The Catalytic Addition of Alkyl Boranes to Alkynyl Esters Affording Single-Isomer Trisubstituted Olefins

  摘要：

  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。

  DOI：

  10.1055/s-0030-1259933
• 作为产物：
  描述：

  5-pentenylbenzoate 、 9-硼双环[3.3.1]壬烷 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 5-(9-borabicyclo[3.3.1]nonan-9-yl)pentyl benzoate
  参考文献：
  名称：

  The Catalytic Addition of Alkyl Boranes to Alkynyl Esters Affording Single-Isomer Trisubstituted Olefins

  摘要：

  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。

  DOI：

  10.1055/s-0030-1259933

文献信息

• 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.
• A simple method to prepare single isomer tetrasubstituted olefins by successive Suzuki–Miyaura cross-couplings of E-β-chloro-α-iodo-α,β-unsaturated esters
  作者：Julie Simard-Mercier、Alison B. Flynn、William W. Ogilvie

  DOI：10.1016/j.tet.2008.04.004

  日期：2008.6

  A convenient method of synthesizing tetrasubstituted olefins as single isomers is described. E-beta-Chloro-alpha-iodo-alpha,beta-unsaturatecl esters are first converted into the corresponding E-beta-chloro-alpha,beta-unsaturatedesters using Suzuki-Miyaura coupling reactions with arylboronic acids and alkenylboronic acids. These transformations gave complete selectivity, and proceeded with substitution at the more activated alpha-iodide position. These compounds, isolated as single isomers, were then transformed into tetrasubstituted olefins by Suzuki-Miyaura couplings with arylboronic acids, alkenylboronic acids, and alkyl boranes to afford the corresponding tetrasubstituted olefins as single isomers. During this coupling process, it was discovered that the use of small ligands, such as PMe3 or PEt3, was critical for efficient coupling. The stereochemistry and regiochemistry of the products were unequivocally established using NMR methods. (C) 2008 Elsevier Ltd. All rights reserved.
• 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。