2-oxo-3a-<3,4-(methylenedioxy)phenyl>-2,3,3a,4,5,6,7,7a-octahydroindole | 7628-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-oxo-3a-<3,4-(methylenedioxy)phenyl>-2,3,3a,4,5,6,7,7a-octahydroindole
• 英文别名: cis-3a-(3,4-methylenedioxyphenyl)-2,3,3a,4,5,6,7,7a-octahydroindol-2-one；3a-benzo[1,3]dioxol-5-yl-(3ar,7ac)-octahydro-indol-2-one；(3aS,7aS)-3a-(1,3-benzodioxol-5-yl)-3,4,5,6,7,7a-hexahydro-1H-indol-2-one
• CAS: 7628-62-8；94027-08-4
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: OPGUOIIUAHEKKQ-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxo-3a-<3,4-(methylenedioxy)phenyl>-2,3,3a,4,5,6,7,7a-octahydroindole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以91%的产率得到3a-(benzo[d][1,3]dioxol-5-yl)octahydro-1H-indole
  参考文献：
  名称：

  Alkaloid synthesis via intramolecular ene reactions. 1. Application to (.+-.)-crinane

  摘要：

  DOI：

  10.1021/ja00401a039
• 作为产物：
  描述：

  3-<3,4-(methylenedioxy)phenyl>-2-cyclohexen-1-one 在 palladium on activated charcoal 吡啶 、 六甲基磷酰三胺 、 sodium tetrahydroborate 、 disodium hydrogenphosphate 、 sodium amalgam 、 氯化亚砜 、 tetrapropylammonium periodate 、 盐酸羟胺 、 氢气 、 sodium carbonate 、 potassium carbonate 、 叔丁基二甲基氯硅烷 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 乙醚 、 乙醇 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 19.33h， 生成 2-oxo-3a-<3,4-(methylenedioxy)phenyl>-2,3,3a,4,5,6,7,7a-octahydroindole
  参考文献：
  名称：

  Alkaloid synthesis via intramolecular ene reactions. 1. Application to (.+-.)-crinane

  摘要：

  DOI：

  10.1021/ja00401a039

文献信息

• A Total Synthesis of (±)-Crinine
  作者：Hans Muxfeldt、Richard S. Schneider、Jared B. Mooberry

  DOI：10.1021/ja00967a052

  日期：1966.8
• Synthetic Studies of <i>cis</i>-3a-Aryloctahydroindole Derivatives by Copper-Catalyzed Cyclization of <i>N</i>-Allyltrichloroacetamides:  Facile Construction of Benzylic Quaternary Carbons by Carbon−Carbon Bond-Forming Reactions
  作者：Sho-ichi Iwamatsu、Kouki Matsubara、Hideo Nagashima

  DOI：10.1021/jo9912146

  日期：1999.12.1

  Cyclization of N-(2-aryl-2-cyclohexen-1-yl)trichloroacetamides by a copper catalyst was investigated. It is crucially important for successful cyclization under mild conditions that alkoxycarbonyl groups are introduced to the nitrogen atom of the N-allyltrichloroacetamides as well as that CuCl(bipyridine) is used as the catalyst. Three compounds, N-(2-phenyl-2-cyclohexen-1-yl)-, N-[2-(3,4-dimethoxyphenyl)-2-cyclohexen-1-yl]-, and N-[2-(3,4-methylenedioxyphenyl)-2-cyclohexen-1-yl]-trichloroacetamides, where the Cbz or MeO2C- group was attached to the nitrogen atom, were instantly converted to the corresponding trichlorinated cis-3a-aryloctahydroindol-2-ones in high yields at room temperature. The reactions offer a facile access to alkaloid skeletons such as mesembrines and crinines; as the simplest examples, total synthesis of (+/-)-mesembrane and (+/-)-crinane was accomplished. The effect of alkoxycarbonyl substituents in the amide group was compared with that of the methyl substituent. N-Methyl-N-(2-phenyl-2-cyclohexen-1-yl)trichloro- acetamide quickly reacted in the presence of CuCl(bipyridine) catalyst; however, the products were a mixture of complicated materials including a small amount of the desired lactam. The role of the alkoxycarbonyl group was discussed in terms of rate of rotation of the N-C bond in the N-allyltrichloroacetamides; variable-temperature NMR studies and X-ray structure determination of related compounds were carried out as supporting evidence.
• Alkaloid synthesis via intramolecular ene reactions. 1. Application to (.+-.)-crinane
  作者：Gary E. Keck、Robert R. Webb

  DOI：10.1021/ja00401a039

  日期：1981.6