1,4-bis[(2R,5S)-2,5-dihydro-2-isopropyl-3,6-dimethoxy-5-propargylpyrazin-5-yl]-2-butyne | 429674-36-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: 1,4-bis[(2R,5S)-2,5-dihydro-2-isopropyl-3,6-dimethoxy-5-propargylpyrazin-5-yl]-2-butyne
• 英文别名: (2R,5R)-5-[4-[(2R,5R)-3,6-dimethoxy-2-propan-2-yl-5-prop-2-ynyl-2H-pyrazin-5-yl]but-2-ynyl]-3,6-dimethoxy-2-propan-2-yl-5-prop-2-ynyl-2H-pyrazine
• CAS: 429674-36-2
• 化学式: C₂₈H₃₈N₄O₄
• 分子量: 494.634
• InChiKey: HLCPSGOEQZJPLO-TUJIQRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  86.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,4-bis[(2R,5S)-2,5-dihydro-2-isopropyl-3,6-dimethoxy-5-propargylpyrazin-5-yl]-2-butyne 在 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 99.0h， 生成 dimethyl (2R,7R)-2,7-diacetamido-2,7-dipropargyl-4-octynedioate
  参考文献：
  名称：

  Ru(II)-Catalyzed Cascade Reactions in Stereocontrolled Construction of Rigid as-Indacene-Bridged Bis(α-amino acid) Derivatives

  摘要：

  The key construction in the preparation of as-indacene-bridged bis(a-amino acid) derivatives was effected by a Ru(II)-catalyzed RCM cascade reaction of appropriately substituted triynes. The latter were available after stepwise and stereocontrolled alkynylations of (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine as chiral auxiliary. The regio- and stereochemical transformations have been verified by a single-crystal X-ray analysis.

  DOI：

  10.1021/jo010888p
• 作为产物：
  描述：

  1,4-bis[(2R,5S)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazin-5-yl]-2-butyne 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.17h， 生成 1,4-bis[(2R,5S)-2,5-dihydro-2-isopropyl-3,6-dimethoxy-5-propargylpyrazin-5-yl]-2-butyne
  参考文献：
  名称：

  Ru(II)-Catalyzed Cascade Reactions in Stereocontrolled Construction of Rigid as-Indacene-Bridged Bis(α-amino acid) Derivatives

  摘要：

  The key construction in the preparation of as-indacene-bridged bis(a-amino acid) derivatives was effected by a Ru(II)-catalyzed RCM cascade reaction of appropriately substituted triynes. The latter were available after stepwise and stereocontrolled alkynylations of (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine as chiral auxiliary. The regio- and stereochemical transformations have been verified by a single-crystal X-ray analysis.

  DOI：

  10.1021/jo010888p

文献信息

• High temperature microwave-accelerated ruthenium-catalysed domino RCM reactions
  作者：Jon Efskind、Kjell Undheim

  DOI：10.1016/s0040-4039(03)00452-0

  日期：2003.3

  The thermal instability of ruthenium(II)-catalyst systems under prolonged heating at 88degreesC in RCM reactions of dienyne and triyne substrates has been circumvented by a microwave temperature increase to 160degreesC when the reaction times were reduced to minutes. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Ru(II)-Catalyzed Cascade Reactions in Stereocontrolled Construction of Rigid <i>as</i>-Indacene-Bridged Bis(α-amino acid) Derivatives
  作者：Gunn Beate Hoven、Jon Efskind、Christian Rømming、Kjell Undheim

  DOI：10.1021/jo010888p

  日期：2002.4.1

  The key construction in the preparation of as-indacene-bridged bis(a-amino acid) derivatives was effected by a Ru(II)-catalyzed RCM cascade reaction of appropriately substituted triynes. The latter were available after stepwise and stereocontrolled alkynylations of (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine as chiral auxiliary. The regio- and stereochemical transformations have been verified by a single-crystal X-ray analysis.