(4R,5R)-4,5-bis(hex-5-enoyl)-2,2-dimethyl-1,3-dioxolane | 874910-09-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-4,5-bis(hex-5-enoyl)-2,2-dimethyl-1,3-dioxolane
• 英文别名: 1-[(4R,5R)-5-hex-5-enoyl-2,2-dimethyl-1,3-dioxolan-4-yl]hex-5-en-1-one
• CAS: 874910-09-5
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: ZFMQLUSEOWYGCZ-HOTGVXAUSA-N

物化性质

• 沸点：
  398.3±42.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  (4R,5R)-4,5-bis(hex-5-enoyl)-2,2-dimethyl-1,3-dioxolane 在 palladium dichloride lead(IV) acetate 、 氧气 、 三氯化铁 、 sodium hydride 、 potassium tri-sec-butyl-borohydride 、 copper(l) chloride 、 magnesium bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 18.5h， 生成 (6R,7R)-6-(benzyloxy)-7-hydroxynonan-2-one
  参考文献：
  名称：

  Enantioselective synthesis of α-benzyloxy-ω-alkenals: application to the synthesis of (+)-exo-brevicomin, (+)-iso-exo-brevicomin, and (−)-isolaurepan

  摘要：

  The enantioselective synthesis of alpha-benzyloxy aldehydes containing a terminal alkene was carried out from chiral Pool L-(+)tartaric acid by employing the stereoselective reduction of a 1,4-diketone as the key step. The synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromones (+)-exo-brevicomin, (+)-iso-exo-brevicomin and a formal synthesis of 2,7cis-disubstituted oxepane (-)-isolaurepan. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.014
• 作为产物：
  描述：

  magnesium,pent-1-ene,bromide 、 (4R,5R)-4-N,5-N-dimethoxy-4-N,5-N,2,2-tetramethyl-1,3-dioxolane-4,5-dicarboxamide 以 四氢呋喃 为溶剂， 反应 1.0h， 以96%的产率得到(4R,5R)-4,5-bis(hex-5-enoyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  （-）-centrolobine的立体选择性形式合成

  摘要：

  利用FeCl 3介导的四氢吡喃的立体选择性形成作为关键步骤，从天然存在的1-（+）-酒石酸中实现（-）-中心罗宾的立体选择性形式合成。

  DOI：

  10.1016/j.tet.2006.11.062

文献信息

• Asymmetric synthesis of both enantiomers of α-methyl-α-methoxyphenylacetic acid from l-(+)-tartaric acid: formal enantioselective synthesis of insect pheromone (−)-frontalin
  作者：Kavirayani R. Prasad、Appayee Chandrakumar、Pazhamalai Anbarasan

  DOI：10.1016/j.tetasy.2006.07.007

  日期：2006.8

  Both antipodes of α-methyl-α-methoxyarylacetic acid derivatives were prepared from a common chiralpool precursor l-(+)-tartaric acid. The key step involves the addition of Grignard reagents to 1,4-diketones derived from tartaric acid. The utility of this strategy was applied in the formal enantioselective synthesis of pine beetle pheromone (−)-frontalin.

  α-甲基-α-甲氧基芳族酸衍生物的两种对映体均由常见的手性池前体1-（+）-酒石酸制备。关键步骤涉及将格氏试剂添加到由酒石酸衍生的1,4-二酮中。该策略的效用被应用于松甲虫信息素（-）-额叶蛋白的正式对映选择性合成中。
• Asymmetric synthesis of unsaturated α-benzyloxyaldehydes: an enantioselective synthesis of (+)-exo-brevicomin
  作者：Kavirayani R. Prasad、Pazhamalai Anbarasan

  DOI：10.1016/j.tetasy.2005.10.035

  日期：2005.12

  Enantioselective synthesis of alpha-hydroxy aldehydes with an alkene tether was accomplished front L-(+)-tartaric acid, employing stereoselective reduction of a 1,4-diketone with L-selectride as the key step. Synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromone (+)-exo-brevicomin. (c) 2005 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of α-benzyloxy-ω-alkenals: application to the synthesis of (+)-exo-brevicomin, (+)-iso-exo-brevicomin, and (−)-isolaurepan
  作者：Kavirayani R. Prasad、Pazhamalai Anbarasan

  DOI：10.1016/j.tetasy.2007.05.014

  日期：2007.7

  The enantioselective synthesis of alpha-benzyloxy aldehydes containing a terminal alkene was carried out from chiral Pool L-(+)tartaric acid by employing the stereoselective reduction of a 1,4-diketone as the key step. The synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromones (+)-exo-brevicomin, (+)-iso-exo-brevicomin and a formal synthesis of 2,7cis-disubstituted oxepane (-)-isolaurepan. (c) 2007 Elsevier Ltd. All rights reserved.
• Stereoselective formal synthesis of (−)-centrolobine
  作者：Kavirayani R. Prasad、Pazhamalai Anbarasan

  DOI：10.1016/j.tet.2006.11.062

  日期：2007.1

  Stereoselective formal synthesis of (−)-centrolobine was achieved from naturally occurring l-(+)-tartaric acid, employing a facile FeCl3 mediated stereoselective formation of a tetrahydropyran as the key step.

  利用FeCl 3介导的四氢吡喃的立体选择性形成作为关键步骤，从天然存在的1-（+）-酒石酸中实现（-）-中心罗宾的立体选择性形式合成。