methyl (3R,4R,5S)-4-(acetylamino)-5-allyl-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate | 335417-54-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (3R,4R,5S)-4-(acetylamino)-5-allyl-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
• 英文别名: methyl (3R,4R,5S)-4-acetamido-3-pentan-3-yloxy-5-prop-2-enylcyclohexene-1-carboxylate
• CAS: 335417-54-4
• 化学式: C₁₈H₂₉NO₄
• 分子量: 323.433
• InChiKey: DYPDPPCFEFBNLI-IAOVAPTHSA-N

物化性质

• 熔点：
  102-103 °C
• 沸点：
  461.5±45.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (3R,4R,5S)-4-(acetylamino)-5-allyl-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以98%的产率得到(3R,4R,5S)-4-(acetylamino)-5-allyl-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, and neuraminidase inhibitory activity of GS-4071 analogues that utilize a novel hydrophobic paradigm

  摘要：

  Structure-based design has led to the synthesis of a novel analogue of GS-4071. an influenza neuraminidase inhibitor, in which the basic amino group has been replaced by a hydrophobic vinyl group. An X-ray co-crystal structure of the new inhibitor (K-i = 45 nM) bound to the actin e site shows that the vinyl group occupies the same subsite as the amino group in GS-4071. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00732-1
• 作为产物：
  描述：

  (1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 偶氮二异丁腈 、 三氟化硼乙醚 、 potassium carbonate 、 氯化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 苯 为溶剂， 生成 methyl (3R,4R,5S)-4-(acetylamino)-5-allyl-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
  参考文献：
  名称：

  Design, synthesis, and neuraminidase inhibitory activity of GS-4071 analogues that utilize a novel hydrophobic paradigm

  摘要：

  Structure-based design has led to the synthesis of a novel analogue of GS-4071. an influenza neuraminidase inhibitor, in which the basic amino group has been replaced by a hydrophobic vinyl group. An X-ray co-crystal structure of the new inhibitor (K-i = 45 nM) bound to the actin e site shows that the vinyl group occupies the same subsite as the amino group in GS-4071. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00732-1

文献信息

• Design, synthesis, and neuraminidase inhibitory activity of GS-4071 analogues that utilize a novel hydrophobic paradigm
  作者：Stephen Hanessian、Jianchio Wang、Debra Montgomery、Vincent Stoll、Kent D. Stewart、Warren Kati、Clarence Maring、Dale Kempf、Charles Hutchins、W.Graeme Laver

  DOI：10.1016/s0960-894x(02)00732-1

  日期：2002.12

  Structure-based design has led to the synthesis of a novel analogue of GS-4071. an influenza neuraminidase inhibitor, in which the basic amino group has been replaced by a hydrophobic vinyl group. An X-ray co-crystal structure of the new inhibitor (K-i = 45 nM) bound to the actin e site shows that the vinyl group occupies the same subsite as the amino group in GS-4071. (C) 2002 Elsevier Science Ltd. All rights reserved.