acetic acid (1R,2R,6R,7R,8R,9R,10S,12S)-9,12-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylene-15-oxatricyclo[6.6.1.0^2,7]pentadec-3-en-10-yl ester | 532384-89-7

• 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: acetic acid (1R,2R,6R,7R,8R,9R,10S,12S)-9,12-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylene-15-oxatricyclo[6.6.1.0^2,7]pentadec-3-en-10-yl ester
• 英文别名: alcyonin；[(1R,2R,6R,7R,8R,9R,10S,12S)-9,12-dihydroxy-3,9-dimethyl-13-methylidene-6-propan-2-yl-15-oxatricyclo[6.6.1.02,7]pentadec-3-en-10-yl] acetate
• CAS: 532384-89-7
• 化学式: C₂₂H₃₄O₅
• 分子量: 378.509
• InChiKey: ZDDYROFVYQUUSR-DIHPLBBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  acetic acid (1R,2R,6R,7R,8R,9R,10S,12S)-9,12-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylene-15-oxatricyclo[6.6.1.0^2,7]pentadec-3-en-10-yl ester 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到klyflaccilin S
  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：

  2,2-dimethylpropionic acid (3S,4S)-bis-(tert-butyldimethylsiloxy)-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 chromium dichloride 、 4-二甲氨基吡啶 、 二甲基硫 、 四丁基氟化铵 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 溶剂黄146 、 nickel dichloride 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 131.17h， 生成 acetic acid (1R,2R,6R,7R,8R,9R,10S,12S)-9,12-dihydroxy-6-isopropyl-3,9-dimethyl-13-methylene-15-oxatricyclo[6.6.1.0^2,7]pentadec-3-en-10-yl 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）。
• KUSUMI, TAKENORI;UCHIDA, HIDEAKI;ISHITSUKA, MIDORI O.;YAMAMOTO, HIROSHI;K+, CHEM. LETT.,(1988) N 6, 1077-1078
  作者：KUSUMI, TAKENORI、UCHIDA, HIDEAKI、ISHITSUKA, MIDORI O.、YAMAMOTO, HIROSHI、K+

  DOI：——

  日期：——
• Alcyonin, a New Cladiellane Diterpene from the Soft Coral<i>Sinularia flexibilis</i>
  作者：Takenori Kusumi、Hideaki Uchida、Midori O. Ishitsuka、Hiroshi Yamamoto、Hiroshi Kakisawa

  DOI：10.1246/cl.1988.1077

  日期：1988.6.5

  The structure of alcyonin, a diterpene isolated from the soft coral Sinularia flexibilis has been determined by spectroscopic and chemical methods.
• Total Synthesis of the Reputed Structure of Alcyonin and Reassignment of Its Structure
  作者：Olivier Corminboeuf、Larry E. Overman、Lewis D. Pennington

  DOI：10.1021/ol034384k

  日期：2003.5.1

  [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.