3-[(1R,2R)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methyl-2-(triethylsilyloxymethyl)-1-[(1Z)-1-trimethylsilyloxypenta-1,4-dienyl]cyclohex-3-en-1-yl]propanenitrile | 1027430-18-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(1R,2R)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methyl-2-(triethylsilyloxymethyl)-1-[(1Z)-1-trimethylsilyloxypenta-1,4-dienyl]cyclohex-3-en-1-yl]propanenitrile
• CAS: 1027430-18-7
• 化学式: C₃₀H₅₃NO₄Si₂
• 分子量: 547.926
• InChiKey: GNBVIXGMPLIBGD-DWBZERAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.49
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[(1R,2R)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methyl-2-(triethylsilyloxymethyl)-1-[(1Z)-1-trimethylsilyloxypenta-1,4-dienyl]cyclohex-3-en-1-yl]propanenitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.17h， 以0.9 mg的产率得到(6R,7R,4'R)-1-but-3-enyl-9-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-8-methyl-7-triethylsilanyloxymethyl-2-azaspiro[5.5]undeca-1,8-diene
  参考文献：
  名称：

  Studies on the Synthesis of Gymnodimine. Construction of the Spiroimine Portion via Diels−Alder Cycloaddition

  摘要：

  [GRAPHICS]An azaspiro[5.5]undecadiene corresponding to a subunit of the shellfish toxin gymnodimine was synthesized by Diels-Alder cycloaddition. One member of the pair of stereoisomeric adducts was transformed to a spiroimine, which will serve as the core around which the macrocyclic portion of the toxin will be assembled.

  DOI：

  10.1021/ol035939e
• 作为产物：
  描述：

  (2S)-2,3-O-isopropylidene-N-methoxy-N-methylpropanamide 在 吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 草酰氯 、 2-thienyl(cyano)copper lithium 、 pH 7 buffer 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 81.33h， 生成 3-[(1R,2R)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methyl-2-(triethylsilyloxymethyl)-1-[(1Z)-1-trimethylsilyloxypenta-1,4-dienyl]cyclohex-3-en-1-yl]propanenitrile
  参考文献：
  名称：

  Studies on the Synthesis of Gymnodimine. Construction of the Spiroimine Portion via Diels−Alder Cycloaddition

  摘要：

  [GRAPHICS]An azaspiro[5.5]undecadiene corresponding to a subunit of the shellfish toxin gymnodimine was synthesized by Diels-Alder cycloaddition. One member of the pair of stereoisomeric adducts was transformed to a spiroimine, which will serve as the core around which the macrocyclic portion of the toxin will be assembled.

  DOI：

  10.1021/ol035939e

文献信息

• Studies on the Synthesis of Gymnodimine. Construction of the Spiroimine Portion via Diels−Alder Cycloaddition
  作者：James D. White、Guoqiang Wang、Laura Quaranta

  DOI：10.1021/ol035939e

  日期：2003.12.1

  [GRAPHICS]An azaspiro[5.5]undecadiene corresponding to a subunit of the shellfish toxin gymnodimine was synthesized by Diels-Alder cycloaddition. One member of the pair of stereoisomeric adducts was transformed to a spiroimine, which will serve as the core around which the macrocyclic portion of the toxin will be assembled.