(S)-(5Z,8Z)-11-[tert-butoxycarbonyl-(2-hydroxyethyl)amino]tetradeca-5,8-dienoic acid allyl ester | 329184-73-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-(5Z,8Z)-11-[tert-butoxycarbonyl-(2-hydroxyethyl)amino]tetradeca-5,8-dienoic acid allyl ester
• 英文别名: prop-2-enyl (5Z,8Z,11S)-11-[2-hydroxyethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]tetradeca-5,8-dienoate
• CAS: 329184-73-8
• 化学式: C₂₄H₄₁NO₅
• 分子量: 423.593
• InChiKey: DAFQWZGINQWKHD-CCECSXMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-(5Z,8Z)-11-[tert-butoxycarbonyl-(2-hydroxyethyl)amino]tetradeca-5,8-dienoic acid allyl ester 在 palladium diacetate 吗啉 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 11.5h， 生成 (S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid 2-[tert-butoxycarbonyl-((S)-(Z)-10-carboxy-1-propyldec-6-enyl)amino]ethyl ester
  参考文献：
  名称：

  Synthesis of Unsaturated Polyazamacrolides from the Ladybird Beetle Subcoccinella vigintiquatuorpunctata

  摘要：

  The pupal defensive secretion of the ladybird beetle Subcoccinella vigintiquatuorpunctata consists of a mixture of macrocyclic polyamines (polyazamacrolides, PAMLs) dominated by three dimeric, 30-membered bislactones (1, 2, and 3), which represent the three possible head-to-tail combinations of the two building blocks (S)-(Z)-11-(2-hydroxyethylamino)-5-tetradecenoic acid (4) and (S)-(5Z,8Z)-11-(2-hydroxyethylamino)-5,8-tetradecadienoic acid (5). We now report the synthesis of these three alkaloids via a route involving the nucleophilic opening of a chiral aziridine as a common step.

  DOI：

  10.1021/jo001200w
• 作为产物：
  描述：

  4-methyl-N-[(S)-1-propyl-5-(tetrahydropyran-2-yloxy)pent-3-ynyl]benzenesulfonamide 在 Lindlar's catalyst 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium hydrogen sulfate 、 copper(l) iodide 、 正丁基锂 、 萘 、 四丁基氟化铵 、 氢气 、 溴 、 sodium 、 sodium hydride 、 N,N'-二环己基碳二亚胺 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 125.0h， 生成 (S)-(5Z,8Z)-11-[tert-butoxycarbonyl-(2-hydroxyethyl)amino]tetradeca-5,8-dienoic acid allyl ester
  参考文献：
  名称：

  Synthesis of Unsaturated Polyazamacrolides from the Ladybird Beetle Subcoccinella vigintiquatuorpunctata

  摘要：

  The pupal defensive secretion of the ladybird beetle Subcoccinella vigintiquatuorpunctata consists of a mixture of macrocyclic polyamines (polyazamacrolides, PAMLs) dominated by three dimeric, 30-membered bislactones (1, 2, and 3), which represent the three possible head-to-tail combinations of the two building blocks (S)-(Z)-11-(2-hydroxyethylamino)-5-tetradecenoic acid (4) and (S)-(5Z,8Z)-11-(2-hydroxyethylamino)-5,8-tetradecadienoic acid (5). We now report the synthesis of these three alkaloids via a route involving the nucleophilic opening of a chiral aziridine as a common step.

  DOI：

  10.1021/jo001200w

文献信息

• Synthesis of Unsaturated Polyazamacrolides from the Ladybird Beetle <i>Subcoccinella </i><i>v</i><i>igintiquatuorpunctata</i>
  作者：Matthew R. Gronquist、Jerrold Meinwald

  DOI：10.1021/jo001200w

  日期：2001.2.1

  The pupal defensive secretion of the ladybird beetle Subcoccinella vigintiquatuorpunctata consists of a mixture of macrocyclic polyamines (polyazamacrolides, PAMLs) dominated by three dimeric, 30-membered bislactones (1, 2, and 3), which represent the three possible head-to-tail combinations of the two building blocks (S)-(Z)-11-(2-hydroxyethylamino)-5-tetradecenoic acid (4) and (S)-(5Z,8Z)-11-(2-hydroxyethylamino)-5,8-tetradecadienoic acid (5). We now report the synthesis of these three alkaloids via a route involving the nucleophilic opening of a chiral aziridine as a common step.