rac-2-(benzoyloxy)hept-6-yn | 742078-66-6

• 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: rac-2-(benzoyloxy)hept-6-yn
• 英文别名: (±)-hept-6-yn-2-yl benzoate；rac-hept-6-yn-2-yl benzoate；Hept-6-yn-2-yl benzoate；hept-6-yn-2-yl benzoate
• CAS: 742078-66-6
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: VHRZRMKIEBEECX-UHFFFAOYSA-N

物化性质

• 沸点：
  311.6±25.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  rac-2-(benzoyloxy)hept-6-yn 在 Lindlar's catalyst 喹啉 、 sodium hydroxide 、 copper(l) iodide 、 四溴化碳 、 氢气 、 potassium carbonate 、 三苯基膦 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 33.0h， 生成 19-hydroxyeicosatetraenoic acid
  参考文献：
  名称：

  Synthesis of (5Z,8Z,11Z,14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-3H8]-analogues through a common synthetic route

  摘要：

  Total synthesis of (5Z,8Z, 11Z, 14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-H-3(8)]-analogues via the corresponding p-toluenesulphonates is reported. This synthetic approach allows the preparation of radioactively labelled arachidonic acid derivatives following a common synthetic route. Activity assays indicated that 15-lipoxygenases may tolerate the azido group in the substrate binding pocket and thus, radioactively labelled azido compounds may be used as photo-affinity probes to investigate mechanistic features of eicosanoid biosynthesis. (C) 2004 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2004.02.008
• 作为产物：
  描述：

  methyl 5-(trimethylsilyl)-4-pentynyl ketone 在 吡啶 、 lithium aluminium tetrahydride 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 10.0h， 生成 rac-2-(benzoyloxy)hept-6-yn
  参考文献：
  名称：

  Synthesis of (5Z,8Z,11Z,14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-3H8]-analogues through a common synthetic route

  摘要：

  Total synthesis of (5Z,8Z, 11Z, 14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-H-3(8)]-analogues via the corresponding p-toluenesulphonates is reported. This synthetic approach allows the preparation of radioactively labelled arachidonic acid derivatives following a common synthetic route. Activity assays indicated that 15-lipoxygenases may tolerate the azido group in the substrate binding pocket and thus, radioactively labelled azido compounds may be used as photo-affinity probes to investigate mechanistic features of eicosanoid biosynthesis. (C) 2004 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2004.02.008

文献信息

• Development of Zn-ProPhenol-Catalyzed Asymmetric Alkyne Addition: Synthesis of Chiral Propargylic Alcohols
  作者：Barry M. Trost、Mark J. Bartlett、Andrew H. Weiss、Axel Jacobi von Wangelin、Vincent S. Chan

  DOI：10.1002/chem.201202085

  日期：2012.12.14

  The development of a general and practical zinc‐catalyzed enantioselective alkyne addition methodology is reported. The commercially available ProPhenol ligand (1) has facilitated the addition of a wide range of zinc alkynylides to aryl, aliphatic, and α,β‐unsaturated aldehydes in high yield and enantioselectivity. New insights into the mechanism of this reaction have resulted in a significant reduction

  报告了一种通用且实用的锌催化对映选择性炔烃加成方法的开发。市售的 ProPhenol 配体 ( 1 ) 有助于以高产率和对映选择性将各种炔基锌添加到芳基、脂肪族和 α,β-不饱和醛中。对该反应机理的新见解导致试剂化学计量的显着减少，从而能够使用珍贵的炔烃并避免使用过量的二甲基锌。来自该反应的对映体富集的炔丙醇用作多功能合成中间体，并且能够有效合成多种复杂的天然产物。
• Transition-Metal-Catalyzed Synthesis of Aspergillide B: An Alkyne Addition Strategy
  作者：Barry M. Trost、Mark J. Bartlett

  DOI：10.1021/ol300200m

  日期：2012.3.2

  catalytic enantioselective formal total synthesis of aspergillide B is reported. This linchpin synthesis was enabled by the development of new conditions for Zn-ProPhenol catalyzed asymmetric alkyne addition. This reaction was used in conjunction with ruthenium-catalyzed trans-hydrosilylation to affect the rapid construction of a late-stage synthetic intermediate of aspergillide B to complete a formal

  报道了曲霉内酯 B 的催化对映选择性形式全合成。这一关键合成是通过开发 Zn-ProPhenol 催化不对称炔加成的新条件而实现的。该反应与钌催化的氢化硅烷化反应结合，影响曲霉内酯B后期合成中间体的快速构建，高效完成曲霉内酯B的正式合成。