2,2-dimethylpropionic acid (3S,4R)-dihydroxy-4-(1R,3R,3aR,7R,7aR)-(7-isopropyl-4-methyl-3-(prop-2-ynyl)-1,3,3a,6,7,7a-hexahydroisobenzofuran-1-yl)pentyl ester | 532382-50-6

• 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: 2,2-dimethylpropionic acid (3S,4R)-dihydroxy-4-(1R,3R,3aR,7R,7aR)-(7-isopropyl-4-methyl-3-(prop-2-ynyl)-1,3,3a,6,7,7a-hexahydroisobenzofuran-1-yl)pentyl ester
• CAS: 532382-50-6
• 化学式: C₂₅H₄₀O₅
• 分子量: 420.59
• InChiKey: XIHUQCBPGUBAFU-WXAJWRORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,2-dimethylpropionic acid (3S,4R)-dihydroxy-4-(1R,3R,3aR,7R,7aR)-(7-isopropyl-4-methyl-3-(prop-2-ynyl)-1,3,3a,6,7,7a-hexahydroisobenzofuran-1-yl)pentyl ester 在 2,6-二甲基吡啶 、 溶剂黄146 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 30.5h， 生成 2,2-dimethylpropionic acid (3S,4S)-bis-(tert-butyldimethylsiloxy)-4-(1R,3R,3aR,7R,7aR)-[3-(2-iodoallyl)-7-isopropyl-4-methyl-1,3,3a,6,7,7a-hexahydroisobenzofuran-1-yl]pentyl ester
  参考文献：
  名称：

  Total Synthesis of the Reputed Structure of Alcyonin and Reassignment of Its Structure

  摘要：

  [GRAPHICS]Introduction of the C4 hydroxyl group by an epoxy ester rearrangement is a pivotal step in the first total synthesis of the purported structure of alcyonin. As the spectral data for diol acetate 3 do not match those reported for alcyonin, the structure of this marine diterpene must be revised. Reexamination of NMR spectra, MS data, and chemical transformations of natural alcyonin suggests that the structure of this marine metabolite is allylic peroxide 15.

  DOI：

  10.1021/ol034384k
• 作为产物：
  描述：

  (1R,3R,3aR,7R,7aR)-2(R)-[3(R)-(7-isopropyl-4-methyl-3-prop-2-ynyl-1,3,3a,6,7,7a-hexahydroisobenzofuran-1-yl)-3-methyloxiranyl]ethanol 在 吡啶 、 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 吡啶 、 甲苯 为溶剂， 反应 5.08h， 生成 2,2-dimethylpropionic acid (3S,4R)-dihydroxy-4-(1R,3R,3aR,7R,7aR)-(7-isopropyl-4-methyl-3-(prop-2-ynyl)-1,3,3a,6,7,7a-hexahydroisobenzofuran-1-yl)pentyl ester
  参考文献：
  名称：

  Total Synthesis of the Reputed Structure of Alcyonin and Reassignment of Its Structure

  摘要：

  [GRAPHICS]Introduction of the C4 hydroxyl group by an epoxy ester rearrangement is a pivotal step in the first total synthesis of the purported structure of alcyonin. As the spectral data for diol acetate 3 do not match those reported for alcyonin, the structure of this marine diterpene must be revised. Reexamination of NMR spectra, MS data, and chemical transformations of natural alcyonin suggests that the structure of this marine metabolite is allylic peroxide 15.

  DOI：

  10.1021/ol034384k

文献信息

• A Unified Strategy for Enantioselective Total Synthesis of Cladiellin and Briarellin Diterpenes: Total Synthesis of Briarellins E and F and the Putative Structure of Alcyonin and Revision of Its Structure Assignment
  作者：Olivier Corminboeuf、Larry E. Overman、Lewis D. Pennington

  DOI：10.1021/jo9010156

  日期：2009.8.7

  Enantioselective total syntheses of briarellin E (12) and briarellin F (13), as well as the structure originally proposed for the cladiellin diterpene alcyonin (10), have been realized. Comparison of the spectral data for synthetic 10, natural alcyonin, cladiellisin (33), and cladiellaperoxide (34), as well as chemical transformations of 10 and natural alcyonin, suggest that the structure of this coral

  briarellin E ( 12 ) 和briarellin F ( 13 ) 的对映选择性全合成，以及最初为cladiellin diterpene alcyonin ( 10 )提出的结构，已经实现。合成10、天然 alcyonin、cladiellisin ( 33 ) 和 cladiellaperoxide ( 34 )的光谱数据的比较，以及10和天然 alcyonin 的化学转化，表明这种珊瑚代谢物的结构是烯丙基过氧化物11。此处详述的统一方法可用于访问 C4-脱氧和 C4-氧化的 cladiellins 和 briarellins。这些合成的核心步骤是（Z )-α,β-不饱和醛17与环己二烯二醇18形成中间体16，其中包含六氢异苯并呋喃核和这些海洋二萜的五个立体中心（方案 1）。