ent-seco-plakortolide I | 1403494-54-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: ent-seco-plakortolide I
• 英文别名: (4R,5R)-4-hydroxy-5-[(2S)-2-hydroxy-2-methyl-12-phenyldodecyl]-5-methyloxolan-2-one
• CAS: 1403494-54-1
• 化学式: C₂₄H₃₈O₄
• 分子量: 390.563
• InChiKey: GFBQUZIAOMGAPQ-YFNKSVMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ent-seco-plakortolide I 、 (S)-(+)-alpha-甲氧基苯乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到(S)-(2R,3R)-2-[(S)-2-hydroxy-2-methyl-12-phenyldodecyl]-2-methyl-5-oxotetrahydrofuran-3-yl 2-methoxy-2-phenylacetate
  参考文献：
  名称：

  Plakortolide Stereochemistry Revisited: The Checkered History of Plakortolides E and I

  摘要：

  The relative configuration of the plakortolide metabolite (4) isolated from a Madagascan Plakortis sp. and named (+)-plakortolide I is revised following reassignment of the C-13 signals for C-7 and C-16, thereby establishing that the metabolite isolated was likely (+)-plakortolide E (3). 'We propose that the name "plakortolide I" should be retained for the plakortolide metabolite 5 first isolated by the Faulkner group; its enantiomer 4 can then be named ent-plakortolide I in line with the description of Barnych and Vatele. The spectroscopic data for MPA esters prepared from synthetic samples of seco derivatives of plakortolide E (3) and ent-plakortolide I (4) were compared with those of MPA esters of seco derivatives from naturally isolated plakortolides L (1) and K (2) and of seco-plakortolide E (6a). Likewise, the spectroscopic data for MTPA esters derived from 3 and 4 were compared with data for the MTPA esters derived from S. These various comparisons established that the sign of the specific rotation associated with the natural isolates is an unreliable indicator of absolute configuration and verify that the absolute configurations of plakortolides L (1), K (2), E (3), and I (5) are (3S, 4S, 6S), (3R, 4R, 6S), (3R, 4R, 6R), and (3S, 4S, 6R), respectively.

  DOI：

  10.1021/np3005634
• 作为产物：
  描述：

  plakortolide I 在 溶剂黄146 、 锌 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以98%的产率得到ent-seco-plakortolide I
  参考文献：
  名称：

  Plakortolide Stereochemistry Revisited: The Checkered History of Plakortolides E and I

  摘要：

  The relative configuration of the plakortolide metabolite (4) isolated from a Madagascan Plakortis sp. and named (+)-plakortolide I is revised following reassignment of the C-13 signals for C-7 and C-16, thereby establishing that the metabolite isolated was likely (+)-plakortolide E (3). 'We propose that the name "plakortolide I" should be retained for the plakortolide metabolite 5 first isolated by the Faulkner group; its enantiomer 4 can then be named ent-plakortolide I in line with the description of Barnych and Vatele. The spectroscopic data for MPA esters prepared from synthetic samples of seco derivatives of plakortolide E (3) and ent-plakortolide I (4) were compared with those of MPA esters of seco derivatives from naturally isolated plakortolides L (1) and K (2) and of seco-plakortolide E (6a). Likewise, the spectroscopic data for MTPA esters derived from 3 and 4 were compared with data for the MTPA esters derived from S. These various comparisons established that the sign of the specific rotation associated with the natural isolates is an unreliable indicator of absolute configuration and verify that the absolute configurations of plakortolides L (1), K (2), E (3), and I (5) are (3S, 4S, 6S), (3R, 4R, 6S), (3R, 4R, 6R), and (3S, 4S, 6R), respectively.

  DOI：

  10.1021/np3005634

文献信息

• Plakortolide Stereochemistry Revisited: The Checkered History of Plakortolides E and I
  作者：Ken W. L. Yong、Bogdan Barnych、James J. De Voss、Jean-Michel Vatèle、Mary J. Garson

  DOI：10.1021/np3005634

  日期：2012.10.26

  The relative configuration of the plakortolide metabolite (4) isolated from a Madagascan Plakortis sp. and named (+)-plakortolide I is revised following reassignment of the C-13 signals for C-7 and C-16, thereby establishing that the metabolite isolated was likely (+)-plakortolide E (3). 'We propose that the name "plakortolide I" should be retained for the plakortolide metabolite 5 first isolated by the Faulkner group; its enantiomer 4 can then be named ent-plakortolide I in line with the description of Barnych and Vatele. The spectroscopic data for MPA esters prepared from synthetic samples of seco derivatives of plakortolide E (3) and ent-plakortolide I (4) were compared with those of MPA esters of seco derivatives from naturally isolated plakortolides L (1) and K (2) and of seco-plakortolide E (6a). Likewise, the spectroscopic data for MTPA esters derived from 3 and 4 were compared with data for the MTPA esters derived from S. These various comparisons established that the sign of the specific rotation associated with the natural isolates is an unreliable indicator of absolute configuration and verify that the absolute configurations of plakortolides L (1), K (2), E (3), and I (5) are (3S, 4S, 6S), (3R, 4R, 6S), (3R, 4R, 6R), and (3S, 4S, 6R), respectively.