2-(2-benzyloxyethyl)-allylmalonate | 188125-31-7

• 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: 2-(2-benzyloxyethyl)-allylmalonate
• 英文别名: Diethyl 2-(2-phenylmethoxyethyl)-2-prop-2-enylpropanedioate
• CAS: 188125-31-7
• 化学式: C₁₉H₂₆O₅
• 分子量: 334.412
• InChiKey: JTBFPFYCWYWTKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-benzyloxyethyl)-allylmalonate 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 lithium chloride 作用下， 以 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 2-(2-Phenylmethoxyethyl)pent-4-enal
  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
• 作为产物：
  描述：

  2-苄氧基乙醇 在 溴 、 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 12.5h， 生成 2-(2-benzyloxyethyl)-allylmalonate
  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

• US6211360B1
  申请人：——

  公开号：US6211360B1

  公开（公告）日：2001-04-03
• 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.