8-Methyl-8-((E)-3-nitro-allyl)-1,4-dioxa-spiro[4.5]decane | 250684-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-Methyl-8-((E)-3-nitro-allyl)-1,4-dioxa-spiro[4.5]decane
• 英文别名: 8-methyl-8-(3-nitroprop-2-enyl)-1,4-dioxaspiro[4.5]decane
• CAS: 250684-23-2
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: VWBSQPBWTMLDBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  8-Methyl-8-((E)-3-nitro-allyl)-1,4-dioxa-spiro[4.5]decane 在 sodium tetrahydroborate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醇 、 水 、 溶剂黄146 为溶剂， 生成 3-methyl-3-(3-nitropropyl)-1,2,3,4-tetrahydrocarbazol-4-one
  参考文献：
  名称：

  Stereoselective preparation of the ABCD tetracycle of the 20-methyl analogue of aspidospermidine and related alkaloids

  摘要：

  The natural cis[ABCD] tetracycle of the 20-methyl analogue of aspidospermidine has been synthesised, starting from the 4,4-ethylenedioxy-1-cyclohexanone. This, was transformed into 3-methyl-3-(3'-nitropropyl)-1,2,3,4-tetrahydrocarbazol-4-one. Two key synthetic steps permits the construction of the D ring: i) the one pot nickel boride catalyst to the imine tetracycle in excellent yield; and ii) the stereoselective reduction of this imine to the natural cis D ring junction in good yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00710-2
• 作为产物：
  描述：

  2-(1,4-二氧杂螺[4.5]癸烷-8-亚基)乙酸乙酯 在 chromium(VI) oxide 、 乙酸铵 、 二异丁基氢化铝 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 生成 8-Methyl-8-((E)-3-nitro-allyl)-1,4-dioxa-spiro[4.5]decane
  参考文献：
  名称：

  Stereoselective preparation of the ABCD tetracycle of the 20-methyl analogue of aspidospermidine and related alkaloids

  摘要：

  The natural cis[ABCD] tetracycle of the 20-methyl analogue of aspidospermidine has been synthesised, starting from the 4,4-ethylenedioxy-1-cyclohexanone. This, was transformed into 3-methyl-3-(3'-nitropropyl)-1,2,3,4-tetrahydrocarbazol-4-one. Two key synthetic steps permits the construction of the D ring: i) the one pot nickel boride catalyst to the imine tetracycle in excellent yield; and ii) the stereoselective reduction of this imine to the natural cis D ring junction in good yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00710-2