Acetic acid (E)-(S)-5-oxo-7-[(E)-3-(3-phenyl-propynoylamino)-allyl]-8,9,11,14-tetrahydro-5H,7H-6,10-dioxa-benzocyclododecen-4-yl ester | 794588-58-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: Acetic acid (E)-(S)-5-oxo-7-[(E)-3-(3-phenyl-propynoylamino)-allyl]-8,9,11,14-tetrahydro-5H,7H-6,10-dioxa-benzocyclododecen-4-yl ester
• 英文别名: [(4S,9E)-2-oxo-4-[(E)-3-(3-phenylprop-2-ynoylamino)prop-2-enyl]-3,7-dioxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraen-16-yl] acetate
• CAS: 794588-58-2
• 化学式: C₂₈H₂₇NO₆
• 分子量: 473.525
• InChiKey: PUXLUFSOCSLWNZ-BSUCBAHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetic acid (E)-(S)-5-oxo-7-[(E)-3-(3-phenyl-propynoylamino)-allyl]-8,9,11,14-tetrahydro-5H,7H-6,10-dioxa-benzocyclododecen-4-yl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以23.6 mg的产率得到3-phenylpropynoic acid [3-(4-hydroxy-5-oxo-8,9,11,14-tetrahydro-5H,7H-6,10-dioxabenzocyclododecen-7-yl)propenyl]amide
  参考文献：
  名称：

  Ring-closing metathesis: a powerful tool for the synthesis of simplified salicylihalamide-based V-ATPase inhibitors

  摘要：

  Based on our synthetic strategy developed for the total synthesis of the macrocyclic salicylate natural product salicylihalamide, we describe herein the synthesis of a series of simplified salicylihalamide-based analogs. Alterations in the aromatic fragment, the macrolactone scaffold and side-chain were evaluated for in vitro inhibition of V-ATPase activity and human tumor cell growth. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.146
• 作为产物：
  描述：

  acetic acid 7-(3-azidocarbonylallyl)-5-oxo-8,9,11,14-tetrahydro-5H,7H-6,10-dioxabenzocyclododecen-7-yl ester 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 5.5h， 生成 Acetic acid (E)-(S)-5-oxo-7-[(E)-3-(3-phenyl-propynoylamino)-allyl]-8,9,11,14-tetrahydro-5H,7H-6,10-dioxa-benzocyclododecen-4-yl ester
  参考文献：
  名称：

  Ring-closing metathesis: a powerful tool for the synthesis of simplified salicylihalamide-based V-ATPase inhibitors

  摘要：

  Based on our synthetic strategy developed for the total synthesis of the macrocyclic salicylate natural product salicylihalamide, we describe herein the synthesis of a series of simplified salicylihalamide-based analogs. Alterations in the aromatic fragment, the macrolactone scaffold and side-chain were evaluated for in vitro inhibition of V-ATPase activity and human tumor cell growth. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.146