(6R)-6-[(1S,2R)-2-[(1E,3R,4S,6Z)-3,4-dihydroxydodeca-1,6-dienyl]cyclopropyl]oxan-2-one | 160523-30-8

• 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: (6R)-6-[(1S,2R)-2-[(1E,3R,4S,6Z)-3,4-dihydroxydodeca-1,6-dienyl]cyclopropyl]oxan-2-one
• CAS: 160523-30-8
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: GUCRVQJMZMFWEY-VBBTXEEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  4-溴苯甲酰氯 、 (6R)-6-[(1S,2R)-2-[(1E,3R,4S,6Z)-3,4-dihydroxydodeca-1,6-dienyl]cyclopropyl]oxan-2-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以53%的产率得到Bis(p-bromobenzoyl)constanolactone E
  参考文献：
  名称：

  Structure and stereochemistry of constanolactones A-G, lactonized cyclopropyl oxylipins from the red marine alga Constantinea simplex

  摘要：

  Extracts of the Oregon marine alga Constantinea simplex were found to contain a mixture of omega 6 and omega 3 unsaturated constanolactones, lactonized cyclopropyl-containing metabolites that logically derive from arachidonic and eicosapentaenoic acids, respectively. Detailed spectroscopic analysis of the isolated compounds, as natural products and various ester derivatives, afforded the planar structures of seven structurally related constanolactones. Constanolactones A-D possess 1,4-diol functionalities while constanolactones E-G contain a vicinal diol functionality. The absolute stereochemistry at all stereocenters in constanolactones A-D and at two stereocenters in constanolactones E and F were determined by chiral chromatography of fragments and chiroptical measurements of various mono- and dibenzoate derivatives and by comparable rotations within the two series (A-D and E-G). Isolation of these various diastereomeric diols, as well as of two presumed methanol adducts from CHCl3/MeOH extraction of C. simplex, leads us to speculate on the occurrence of highly unstable allylic epoxides in this red alga.

  DOI：

  10.1021/jo00103a012
• 作为产物：
  描述：

  n-溴代已基三苯基膦 在 吡啶 、 六甲基磷酰三胺 、 sodium chlorite 、 disodium hydrogenphosphate 、 sodium dihydrogenphosphate 、 重铬酸吡啶 、 正丁基锂 、 sodium amalgam 、 2-甲基-2-丁烯 、 草酰氯 、 4 A molecular sieve 、 四丁基氟化铵 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 47.75h， 生成 (6R)-6-[(1S,2R)-2-[(1E,3R,4S,6Z)-3,4-dihydroxydodeca-1,6-dienyl]cyclopropyl]oxan-2-one
  参考文献：
  名称：

  Total Synthesis of Constanolactone E, a Marine Eicosanoid from the Alga Constantinea simplex; Absolute Structure of Constanolactone E

  摘要：

  DOI：

  10.3987/com-97-s(n)58

文献信息

• Synthesis of constanolactone E
  作者：Hiroaki Miyaoka、Tatsuya Shigemoto、Yasuji Yamada

  DOI：10.1016/0040-4039(96)01692-9

  日期：1996.10

  Synthesis of marine eicosanoid constanolactone E was achieved through the one-pot formation of chiral cyclopropane derivative 4 using the anion of allyl phenyl sulfone and chiral epoxymesylate 3.

  通过使用烯丙基苯基砜和手性环氧甲磺酸酯3的阴离子一锅法形成手性环丙烷衍生物4，实现了海洋类二十烷酸甾醇内酯E的合成。
• Total Synthesis of Constanolactone E, a Marine Eicosanoid from the Alga Constantinea simplex; Absolute Structure of Constanolactone E
  作者：Yasuji Yamada、Hiroaki Miyaoka、Tatsuya Shigemoto

  DOI：10.3987/com-97-s(n)58

  日期：——
• Structure and stereochemistry of constanolactones A-G, lactonized cyclopropyl oxylipins from the red marine alga Constantinea simplex
  作者：Dale G. Nagle、William H. Gerwick

  DOI：10.1021/jo00103a012

  日期：1994.12

  Extracts of the Oregon marine alga Constantinea simplex were found to contain a mixture of omega 6 and omega 3 unsaturated constanolactones, lactonized cyclopropyl-containing metabolites that logically derive from arachidonic and eicosapentaenoic acids, respectively. Detailed spectroscopic analysis of the isolated compounds, as natural products and various ester derivatives, afforded the planar structures of seven structurally related constanolactones. Constanolactones A-D possess 1,4-diol functionalities while constanolactones E-G contain a vicinal diol functionality. The absolute stereochemistry at all stereocenters in constanolactones A-D and at two stereocenters in constanolactones E and F were determined by chiral chromatography of fragments and chiroptical measurements of various mono- and dibenzoate derivatives and by comparable rotations within the two series (A-D and E-G). Isolation of these various diastereomeric diols, as well as of two presumed methanol adducts from CHCl3/MeOH extraction of C. simplex, leads us to speculate on the occurrence of highly unstable allylic epoxides in this red alga.