(3R)-3-(1-bromoethenyl)-1,4-dioxaspiro[4.4]nonane | 900518-86-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R)-3-(1-bromoethenyl)-1,4-dioxaspiro[4.4]nonane
• CAS: 900518-86-7
• 化学式: C₉H₁₃BrO₂
• 分子量: 233.105
• InChiKey: BTBZNBPRIBABGG-MRVPVSSYSA-N

物化性质

• 沸点：
  298.5±25.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R)-3-(1-bromoethenyl)-1,4-dioxaspiro[4.4]nonane 在 吡啶 、 chromium dichloride 、 4-二甲氨基吡啶 、 palladium diacetate 、 L-丝氨酸 、 碳酸氢钠 、 三苯基膦 、 calcium carbonate 、 nickel dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成 [(2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-3-[(4S,5S)-5-[(1E)-3-[(3S)-1,4-dioxaspiro[4.4]nonan-3-yl]buta-1,3-dienyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylpropyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Unified Total Synthesis of Pteriatoxins and Their Diastereomers

  摘要：

  A unified total synthesis is reported to access all of the possible diastereomers of pteriatoxins A-C, with the use of an intramolecular Diels-Alder reaction as the key step to form the carbo-macrocyclic core structure. The C34/C35-diol protecting groups were found to have significant effects on both the exo/endo-selectivity and the exo-facial selectivity of the intramolecular Diels-Alder process.

  DOI：

  10.1021/ja0618954
• 作为产物：
  描述：

  环戊酮 、 2-bromo-1-butene-3,4-diol 在 magnesium sulfate 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 18.0h， 以79%的产率得到(3R)-3-(1-bromoethenyl)-1,4-dioxaspiro[4.4]nonane
  参考文献：
  名称：

  Unified Total Synthesis of Pteriatoxins and Their Diastereomers

  摘要：

  A unified total synthesis is reported to access all of the possible diastereomers of pteriatoxins A-C, with the use of an intramolecular Diels-Alder reaction as the key step to form the carbo-macrocyclic core structure. The C34/C35-diol protecting groups were found to have significant effects on both the exo/endo-selectivity and the exo-facial selectivity of the intramolecular Diels-Alder process.

  DOI：

  10.1021/ja0618954

文献信息

• Diastereoselective Intramolecular Carbamoylketene/Alkene [2 + 2] Cycloaddition: Enantioselective Access to Pyrrolidinoindoline Alkaloids
  作者：Takaaki Araki、Tsukasa Ozawa、Hiromasa Yokoe、Makoto Kanematsu、Masahiro Yoshida、Kozo Shishido

  DOI：10.1021/ol303204v

  日期：2013.1.4

  A novel and highly diastereoselective intramolecular carbamoylketene/alkene [2 + 2] cycloaddition has been developed, and the methodology was successfully applied to the enantioselective syntheses of (−)-esermethole and Takayama’s intermediate for (+)-psychotrimine.

  已开发出一种新颖的，高度非对映选择性的分子内氨基甲酰基乙烯酮/烯烃[2 + 2]环加成反应，该方法已成功地应用于（-）-乙二胺和高山的（+）-精神三胺中间体的对映选择性合成。
• Unified Total Synthesis of Pteriatoxins and Their Diastereomers
  作者：Fumiyoshi Matsuura、René Peters、Masahiro Anada、Scott S. Harried、Junliang Hao、Yoshito Kishi

  DOI：10.1021/ja0618954

  日期：2006.6.1

  A unified total synthesis is reported to access all of the possible diastereomers of pteriatoxins A-C, with the use of an intramolecular Diels-Alder reaction as the key step to form the carbo-macrocyclic core structure. The C34/C35-diol protecting groups were found to have significant effects on both the exo/endo-selectivity and the exo-facial selectivity of the intramolecular Diels-Alder process.