8-benzoyloxyoctanal | 354563-56-7

• 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: 8-benzoyloxyoctanal
• 英文别名: 8-(benzoyloxy)Octanal；8-oxooctyl benzoate
• CAS: 354563-56-7
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: URURRZCJVZKBFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  8-benzoyloxyoctanal 在 sodium tetrahydroborate 、 盐酸二甲胺 、 三乙胺 、 sodium iodide 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 40.5h， 生成 benzoic acid 7-iodomethyloct-7-enyl ester
  参考文献：
  名称：

  Evaluation of possible intramolecular [4+2] cycloaddition routes for assembling the central tetracyclic core of the potent marine antiinflammatory agent mangicol A

  摘要：

  A plan for enantioselective construction of the mangicol A framework by means of intramolecular Diels-Alder cycloaddition is outlined. First to be assembled is the enantiopure cyclopentenecarboxylic acid 16. Of the several approaches targeting the 1,3-diene component 56, only that involving palladium-catalyzed enyne cyclization proved successful. Following the coupling of 16 to 56, we were unable to bring about any detectable level of (4 pi+2 pi) cycloaddition. Activation of the diene by incorporation of an OSiEt3 substituent on a terminal sp(2)-hybridized center likewise proved unsuccessful. Further facilitation was sought in the form of cyclopentenonecarboxylate 66. However, thermal activation, Lewis acid catalysis, and high-pressure conditions proved ineffective and did not lead to C-C bond formation. These studies serve to underscore the extent to which steric complications can complicate matters and the extent to which they must be skirted to arrive at the title compound. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.096
• 作为产物：
  描述：

  1,8-辛二醇 在 4-二甲氨基吡啶 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 8-benzoyloxyoctanal
  参考文献：
  名称：

  Evaluation of possible intramolecular [4+2] cycloaddition routes for assembling the central tetracyclic core of the potent marine antiinflammatory agent mangicol A

  摘要：

  A plan for enantioselective construction of the mangicol A framework by means of intramolecular Diels-Alder cycloaddition is outlined. First to be assembled is the enantiopure cyclopentenecarboxylic acid 16. Of the several approaches targeting the 1,3-diene component 56, only that involving palladium-catalyzed enyne cyclization proved successful. Following the coupling of 16 to 56, we were unable to bring about any detectable level of (4 pi+2 pi) cycloaddition. Activation of the diene by incorporation of an OSiEt3 substituent on a terminal sp(2)-hybridized center likewise proved unsuccessful. Further facilitation was sought in the form of cyclopentenonecarboxylate 66. However, thermal activation, Lewis acid catalysis, and high-pressure conditions proved ineffective and did not lead to C-C bond formation. These studies serve to underscore the extent to which steric complications can complicate matters and the extent to which they must be skirted to arrive at the title compound. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.096

文献信息

• Catalytic nucleophilic activation of acetonitrile via a cooperative catalysis of cationic Ru complex, DBU, and NaPF6
  作者：Naoya Kumagai、Shigeki Matsunaga、Masakatsu Shibasaki

  DOI：10.1016/j.tet.2007.04.051

  日期：2007.8

  mild amine basic conditions is described. A cooperative catalysis of CpRu complex, DBU, and NaPF6 enables chemoselective and catalytic generation of nucleophiles from barely acidic acetonitrile, which is integrated into the addition to aldehydes, imines, and activated ketones. Mechanistic investigations revealed that the three catalyst components work together to achieve high catalytic efficiency.

  描述了在温和的胺碱性条件下直接添加乙腈的有效催化系统的开发。CpRu络合物，DBU和NaPF 6的协同催化能够从勉强酸性的乙腈进行化学选择和催化生成亲核试剂，并将其整合到醛，亚胺和活化的酮中。机理研究表明，三种催化剂组分共同作用以实现高催化效率。
• Catalytic chemoselective addition of acetonitrile to enolizable aldehydes with cationic Ru complex/DBU combination
  作者：Naoya Kumagai、Shigeki Matsunaga、Masakatsu Shibasaki

  DOI：10.1039/b504519c

  日期：——

  The cooperative catalysis of CpRu(PPh3)2(CH3CN)PF6 (1b) and DBU enables chemoselective nucleophilic activation of acetonitrile in the presence of base-sensitive aldehydes 2 to afford corresponding β-hydroxynitriles 3 in good yield.

  CpRu(PPh3)2(CH3CN)PF6 (1b)与DBU的协同催化作用，能够在存在对碱敏感的醛2的情况下，以良好的产率实现乙腈的选择性亲核活化，从而得到相应的β-羟基腈3。
• Catalytic Asymmetric Synthesis of syn Aldols with Methyl Ketone Functionality and anti Aldols with a Thioamide Group
  作者：Naoya Kumagai、Masakatsu Shibasaki、Yuya Ota、Zhao Li

  DOI：10.1055/s-0037-1610690

  日期：2019.3

  Catalytic asymmetric syntheses of syn aldols with a methyl ketone functionality were studied to confirm the generality of the methodology. In addition, catalytic asymmetric synthesis of anti aldols with a thioamide group was carefully examined, giving the desired products, albeit with moderate diastereoselectivity.

  研究了具有甲基酮官能团的合成羟醛的催化不对称合成，以确认该方法的通用性。此外，仔细研究了具有硫代酰胺基团的抗醛醇的催化不对称合成，得到了所需的产物，尽管具有中等的非对映选择性。
• Sulfenamide Catalyzed Oxidation of Alcohols to the Corresponding Carbonyl Compounds with Anhydrous Chloramine-T
  作者：Hideo Kitagawa、Teruaki Mukaiyama

  DOI：10.1248/cpb.50.1276

  日期：——

  N-tert-Butylbenzenesulfenamide (1) catalyzed oxidation of various alcohols with stoichiometric amount of anhydrous chloramines-T (2) proceeded smoothly at room temperature to afford the corresponding carbonyl compounds in good yields.

  用化学计量的无水氯胺-T（2）进行的各种醇的N-叔丁基苯亚磺酰胺（1）催化的氧化在室温下平稳进行，以良好的收率得到相应的羰基化合物。
• Direct Catalytic Asymmetric Aldol Reaction of Thioamide with an α‐Vinyl Appendage
  作者：Jin Cui、Akimichi Ohtsuki、Takumi Watanabe、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.1002/chem.201800020

  日期：2018.2.21

  asymmetric aldol reaction is an emerging catalytic methodology that provides atom‐economical access to functionalized chiral building blocks. Thioamides are useful aldol donors due to their high‐fidelity chemoselective enolization and divergent post‐aldol transformations. Herein we describe the incorporation of an α‐vinyl appendage on a thioamide, which expands the utility of aldol adducts for natural

  直接催化不对称醛醇缩合反应是一种新兴的催化方法，它提供了经济实用的手性结构单元的经济途径。硫酰胺由于其高保真化学选择性烯醇化和发散后的醛醇转化而成为有用的醛醇供体。在本文中，我们描述了在硫酰胺上掺入α-乙烯基附件，这扩大了醛醇加合物用于天然产物合成的效用。在先前确定的催化剂设置下不能容纳这种乙烯基化的硫代酰胺，但是新开发的催化条件提供了含有侧基乙烯基的羟醛产物。