methyl (E)-4-[(3S,4S,7S,8S,9R,12S,23R,24S,28S)-7,24-dihydroxy-3,4,8,20,20,22,22-heptamethyl-27-oxo-28-prop-1-en-2-yl-21-oxa-1-azaoctacyclo[13.13.1.02,14.03,12.04,9.017,25.018,23.026,29]nonacosa-2(14),15,17(25),18,26(29)-pentaen-8-yl]but-3-enoate | 502179-88-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (E)-4-[(3S,4S,7S,8S,9R,12S,23R,24S,28S)-7,24-dihydroxy-3,4,8,20,20,22,22-heptamethyl-27-oxo-28-prop-1-en-2-yl-21-oxa-1-azaoctacyclo[13.13.1.02,14.03,12.04,9.017,25.018,23.026,29]nonacosa-2(14),15,17(25),18,26(29)-pentaen-8-yl]but-3-enoate
• CAS: 502179-88-6
• 化学式: C₄₂H₅₃NO₆
• 分子量: 667.886
• InChiKey: IQUYXMGSQWKEPZ-ZTWIQMEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  49
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  98
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (E)-4-[(3S,4S,7S,8S,9R,12S,23R,24S,28S)-7,24-dihydroxy-3,4,8,20,20,22,22-heptamethyl-27-oxo-28-prop-1-en-2-yl-21-oxa-1-azaoctacyclo[13.13.1.02,14.03,12.04,9.017,25.018,23.026,29]nonacosa-2(14),15,17(25),18,26(29)-pentaen-8-yl]but-3-enoate 在 bis-triphenylphosphine-palladium(II) chloride 、 titanium tetra-n-propoxide 、 三正丁基氢锡 作用下， 生成 (E)-4-[(3S,4S,7S,8S,9R,12S,23R,24S,28S)-7,24-dihydroxy-3,4,8,20,20,22,22-heptamethyl-27-oxo-28-prop-1-en-2-yl-21-oxa-1-azaoctacyclo[13.13.1.02,14.03,12.04,9.017,25.018,23.026,29]nonacosa-2(14),15,17(25),18,26(29)-pentaen-8-yl]but-3-enoic acid
  参考文献：
  名称：

  Nodulisporic acid side-Chain modifications: access to the 2″, 3″, 4″, and 6″ registers

  摘要：

  Efficient routes to access the 2", 3", 4", and 6" registers of the nodulisporic acid (NsA) side chain are disclosed. A mild one-carbon, Ph2C=NCH(2)Cequivalent toN mediated homologation of NsA's 3"-aldehyde permitted access to the 4"-register. Curtius reaction of NsA's 3"-acid yielded the corresponding 2"-aldehyde 4 from which the unnatural Delta(2" 3")-olefin isomer 2b was obtained. In addition, Arndt-Eistert reactions of the parent NsA permitted a one-carbon homologation to the 6" register. These efforts identified new analogues with significant flea activity and illustrated the biological significance of unsaturation at the 1",2" register. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00826-0
• 作为产物：
  描述：

  在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 4-甲基苯磺酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (E)-4-[(3S,4S,7S,8S,9R,12S,23R,24S,28S)-7,24-dihydroxy-3,4,8,20,20,22,22-heptamethyl-27-oxo-28-prop-1-en-2-yl-21-oxa-1-azaoctacyclo[13.13.1.02,14.03,12.04,9.017,25.018,23.026,29]nonacosa-2(14),15,17(25),18,26(29)-pentaen-8-yl]but-3-enoate
  参考文献：
  名称：

  Nodulisporic acid side-Chain modifications: access to the 2″, 3″, 4″, and 6″ registers

  摘要：

  Efficient routes to access the 2", 3", 4", and 6" registers of the nodulisporic acid (NsA) side chain are disclosed. A mild one-carbon, Ph2C=NCH(2)Cequivalent toN mediated homologation of NsA's 3"-aldehyde permitted access to the 4"-register. Curtius reaction of NsA's 3"-acid yielded the corresponding 2"-aldehyde 4 from which the unnatural Delta(2" 3")-olefin isomer 2b was obtained. In addition, Arndt-Eistert reactions of the parent NsA permitted a one-carbon homologation to the 6" register. These efforts identified new analogues with significant flea activity and illustrated the biological significance of unsaturation at the 1",2" register. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00826-0