4-(1,3-dioxolan-2-yl)-6-methoxy-1-hexene | 188125-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 4-(1,3-dioxolan-2-yl)-6-methoxy-1-hexene
• 英文别名: 2-(1-Methoxyhex-5-en-3-yl)-1,3-dioxolane
• CAS: 188125-28-2
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: CJNWZPQHDNKHOL-UHFFFAOYSA-N

物化性质

• 沸点：
  245.7±25.0 °C(Predicted)
• 密度：
  0.978±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1,3-dioxolan-2-yl)-6-methoxy-1-hexene 在 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 4-(1,3-dioxolan-2-yl)-6-methoxy-1-hexanal
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 18-Methoxycoronaridine Congeners. Potential Antiaddiction Agents

  摘要：

  Variation of the methoxycarbonyl and C-18 substituents of the antiaddictive compound 18-methoxycoronaridine, and contraction of its isoquinuclidine ring segment, provided 15 congeners for SAR evaluation at opioid and alpha3beta4 nicotinic acetylcholine receptors. The opioid activities were relatively low, and the alpha3beta4 nicotinic acetylcholine receptor activities were found to correlate with in vivo antiaddictive activities.

  DOI：

  10.1021/jm020562o
• 作为产物：
  描述：

  烯丙基丙二酸二乙酯 在 对甲苯磺酸 lithium aluminium tetrahydride 、 草酰氯 、 sodium ethanolate 、 二甲基亚砜 、 三乙胺 、 lithium chloride 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 24.0h， 生成 4-(1,3-dioxolan-2-yl)-6-methoxy-1-hexene
  参考文献：
  名称：

  Total syntheses of racemic albifloranine and its anti-addictive congeners, including 18-methoxycoronaridine

  摘要：

  Condensation of methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate (12) with 4-(1,3-dioxolan-2-yl)-6-benzylaxyhexanal (11a) provided the tetracyclic intermediates methyl (3aSR,4RS,11bRS)-3-benzyl-2,3,3a,4,5,7-hexahydro-4-[2-zeta-(1,3-dioxalan-2-yl)-4-benzyloxy)-1-butyl]-1H-pyrrolo[2,3-d]carbazole-6-carboxylates (14a,15a), which were further elaborated to afford racemic albifloranine (3). The first total synthesis of albifloranine was completed in 13 steps, with an overall 7% yield. Ester and ether derivatives of albifloranine were synthesized for evaluation as anti-addictive agents. Among these, 18-methoxycoronaridine (20b) stands out as a nontoxic agent that significantly reduces demand for morphine, cocaine, nicotine and alcohol in rats. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00513-x

文献信息

• Efficient Preparation of the 18-Methoxycoronaridine Side-Chain Precursor
  作者：R. Herr、Matthew Rainka、Matthew Dowling、Chi-Hsin King、Harold Meckler

  DOI：10.1055/s-2006-942489

  日期：2006.8

  An efficient synthesis of the side-chain precursor crucial to the preparation of 18-methoxycoronaridine (18-MC) has been developed. This procedure represents an improvement upon the original synthesis, in which regioisomers were separated by chromatography to provide the requisite precursor. Incorporation of the protected primary alcohol moiety in the early stages of the synthesis provides the requisite regioisomer unambiguously and obviates the need for chromatography at any point.

  对制备 18-甲氧基可可碱（18-MC）至关重要的侧链前体的高效合成方法已经开发出来。这种合成方法改进了原来的合成方法，即通过色谱法分离regioisomers来提供所需的前体。在合成的早期阶段加入受保护的伯醇分子，可以明确地提供所需的区域异构体，而无需在任何阶段进行色谱分析。
• IBOGAMINE CONGENERS
  申请人：ALBANY MEDICAL COLLEGE

  公开号：EP0859610B1

  公开（公告）日：2006-01-11
• Total syntheses of racemic albifloranine and its anti-addictive congeners, including 18-methoxycoronaridine
  作者：Upul K. Bandarage、Martin E. Kuehne、Stanley D. Glick

  DOI：10.1016/s0040-4020(99)00513-x

  日期：1999.7

  Condensation of methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate (12) with 4-(1,3-dioxolan-2-yl)-6-benzylaxyhexanal (11a) provided the tetracyclic intermediates methyl (3aSR,4RS,11bRS)-3-benzyl-2,3,3a,4,5,7-hexahydro-4-[2-zeta-(1,3-dioxalan-2-yl)-4-benzyloxy)-1-butyl]-1H-pyrrolo[2,3-d]carbazole-6-carboxylates (14a,15a), which were further elaborated to afford racemic albifloranine (3). The first total synthesis of albifloranine was completed in 13 steps, with an overall 7% yield. Ester and ether derivatives of albifloranine were synthesized for evaluation as anti-addictive agents. Among these, 18-methoxycoronaridine (20b) stands out as a nontoxic agent that significantly reduces demand for morphine, cocaine, nicotine and alcohol in rats. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis and Biological Evaluation of 18-Methoxycoronaridine Congeners. Potential Antiaddiction Agents
  作者：Martin E. Kuehne、Liwen He、Patrick A. Jokiel、C. J. Pace、M. W. Fleck、I. M. Maisonneuve、Stanley D. Glick、Jean M. Bidlack

  DOI：10.1021/jm020562o

  日期：2003.6.1

  Variation of the methoxycarbonyl and C-18 substituents of the antiaddictive compound 18-methoxycoronaridine, and contraction of its isoquinuclidine ring segment, provided 15 congeners for SAR evaluation at opioid and alpha3beta4 nicotinic acetylcholine receptors. The opioid activities were relatively low, and the alpha3beta4 nicotinic acetylcholine receptor activities were found to correlate with in vivo antiaddictive activities.