(+/-)-(1R,5R,6S)-8-benzyloxycarbonyl-6-(1-methyl-1,1-dioxacyclopentyl)-8-azabicyclo[3.2.1]oct-3-en-2-one

• 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: (+/-)-(1R,5R,6S)-8-benzyloxycarbonyl-6-(1-methyl-1,1-dioxacyclopentyl)-8-azabicyclo[3.2.1]oct-3-en-2-one
• 英文别名: benzyl (1R,5R,7S)-7-(2-methyl-1,3-dioxolan-2-yl)-4-oxo-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: OIHSGEYELRGHPH-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-(1R,5R,6S)-8-benzyloxycarbonyl-6-(1-methyl-1,1-dioxacyclopentyl)-8-azabicyclo[3.2.1]oct-3-en-2-one 在 Wilkinson's catalyst 氢气 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 24.0h， 以85%的产率得到(+/-)-(1R,5R,6S)-8-benzyloxycarbonyl-6-(1-methyl-1,1-dioxacyclopentyl)-8-azabicyclo[3.2.1]octan-2-one
  参考文献：
  名称：

  Organometallic Enantiomeric Scaffolding:  Organometallic Chirons. Total Synthesis of (−)-Bao Gong Teng A by a Molybdenum-Mediated [5+2] Cycloaddition

  摘要：

  Bao Gong Teng A, an optically active tropane alkaloid with hypotensive and miotic activity isolated from the Chinese herb Erycibe obtusifolia Benth, was synthesized by an "organometallic Chiron" strategy in which single enantiomers of TpMo(CO)(2)(eta(3)-pyriclinyl) complexes are produced in quantity and then elaborated easily and efficiently to generate, after demetalation, highly enantiopure advanced synthetic intermediates possessing the tropane core.

  DOI：

  10.1021/ja055623x
• 作为产物：
  描述：

  2-乙基-2-甲基-1,3-二氧杂烷 、 (+/-)-(1R,5R,6S)-6-acetyl-8-benzyloxycarbonyl-8-azabicyclo[3.2.1]oct-3-en-2-one 在 三氟化硼乙醚 作用下， 以 氯仿 、 乙二醇 为溶剂， 反应 0.58h， 以82%的产率得到(+/-)-(1R,5R,6S)-8-benzyloxycarbonyl-6-(1-methyl-1,1-dioxacyclopentyl)-8-azabicyclo[3.2.1]oct-3-en-2-one
  参考文献：
  名称：

  Organometallic Enantiomeric Scaffolding:  Organometallic Chirons. Total Synthesis of (−)-Bao Gong Teng A by a Molybdenum-Mediated [5+2] Cycloaddition

  摘要：

  Bao Gong Teng A, an optically active tropane alkaloid with hypotensive and miotic activity isolated from the Chinese herb Erycibe obtusifolia Benth, was synthesized by an "organometallic Chiron" strategy in which single enantiomers of TpMo(CO)(2)(eta(3)-pyriclinyl) complexes are produced in quantity and then elaborated easily and efficiently to generate, after demetalation, highly enantiopure advanced synthetic intermediates possessing the tropane core.

  DOI：

  10.1021/ja055623x

文献信息

• Organometallic Enantiomeric Scaffolding:  Organometallic Chirons. Total Synthesis of (−)-Bao Gong Teng A by a Molybdenum-Mediated [5+2] Cycloaddition
  作者：Yongqiang Zhang、Lanny S. Liebeskind

  DOI：10.1021/ja055623x

  日期：2006.1.1

  Bao Gong Teng A, an optically active tropane alkaloid with hypotensive and miotic activity isolated from the Chinese herb Erycibe obtusifolia Benth, was synthesized by an "organometallic Chiron" strategy in which single enantiomers of TpMo(CO)(2)(eta(3)-pyriclinyl) complexes are produced in quantity and then elaborated easily and efficiently to generate, after demetalation, highly enantiopure advanced synthetic intermediates possessing the tropane core.