(6Z,9R)-4,5,8,9-tetrahydro-9-[(1E,3S,4S,6Z)-4-hydroxy-3-methoxy-1,6-dodecadienyl]-2(3H)-oxoninone | 886193-10-8

• 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: (6Z,9R)-4,5,8,9-tetrahydro-9-[(1E,3S,4S,6Z)-4-hydroxy-3-methoxy-1,6-dodecadienyl]-2(3H)-oxoninone
• 英文别名: (2R,4Z)-2-[(1E,3S,4S,6Z)-4-hydroxy-3-methoxydodeca-1,6-dienyl]-3,6,7,8-tetrahydro-2H-oxonin-9-one
• CAS: 886193-10-8
• 化学式: C₂₁H₃₄O₄
• 分子量: 350.499
• InChiKey: NGVOPKDYDKTASH-KMRPYSECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6Z,9R)-4,5,8,9-tetrahydro-9-[(1E,3S,4S,6Z)-4-hydroxy-3-methoxy-1,6-dodecadienyl]-2(3H)-oxoninone 在 甲醇 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 13.0h， 生成 (2R,4Z)-2-[(1E,3S,4R,6Z)-4-hydroxy-3-methoxydodeca-1,6-dienyl]-3,6,7,8-tetrahydro-2H-oxonin-9-one
  参考文献：
  名称：

  Stereochemical assignment of topsentolide C2 by stereodivergent synthesis of its four diastereomers

  摘要：

  Four diastereomers of topsentolide C-2, a cytotoxic nine-membered lactone isolated from the marine sponge Topsentia sp., were synthesized stereodivergently from a common chiral seco acid by the combined use of the Yamaguchi and Mitsunobu lactonizations. Comparison of the NMR spectra of the four diastereomers with those of an authentic sample of topsentolide C-2 led to the stereochemical determination of topsentolide C-2 as 8R, 11S, and 12S. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.032
• 作为产物：
  描述：

  (6Z,9R)-4,5,8,9-tetrahydro-9-[(1E,3S,4S,6Z)-3-methoxy-4-(4-methoxyphenyl)methoxy-1,6-dodecadienyl]-2(3H)-oxoninone 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以99%的产率得到(6Z,9R)-4,5,8,9-tetrahydro-9-[(1E,3S,4S,6Z)-4-hydroxy-3-methoxy-1,6-dodecadienyl]-2(3H)-oxoninone
  参考文献：
  名称：

  Synthesis of topsentolides A2 and C2, and non-enzymatic conversion of the former to the latter

  摘要：

  The first total synthesis of the marine-derived cytotoxin topsentolide A(2), which eventually culminated in its stereochemical determination, was accomplished in 17 steps from a known chiral alcohol. An improved synthesis of its congener, topsentolide C-2, from a synthetic intermediate of topsentolide A(2) was also performed by utilizing the Yamaguchi lactonization to construct its nine-membered lactone ring. Treatment of epoxide ring-containing topsentolide Ay with HCl/MeOH brought about its quantitative conversion into topsentolide C-2. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.040

文献信息

• Synthesis of topsentolides A2 and C2, and non-enzymatic conversion of the former to the latter
  作者：Ryo Towada、Shigefumi Kuwahara

  DOI：10.1016/j.tet.2014.04.040

  日期：2014.6

  The first total synthesis of the marine-derived cytotoxin topsentolide A(2), which eventually culminated in its stereochemical determination, was accomplished in 17 steps from a known chiral alcohol. An improved synthesis of its congener, topsentolide C-2, from a synthetic intermediate of topsentolide A(2) was also performed by utilizing the Yamaguchi lactonization to construct its nine-membered lactone ring. Treatment of epoxide ring-containing topsentolide Ay with HCl/MeOH brought about its quantitative conversion into topsentolide C-2. (C) 2014 Elsevier Ltd. All rights reserved.
• Stereochemical assignment of topsentolide C2 by stereodivergent synthesis of its four diastereomers
  作者：Ryo Towada、Yusuke Kurashina、Shigefumi Kuwahara

  DOI：10.1016/j.tetlet.2013.10.032

  日期：2013.12

  Four diastereomers of topsentolide C-2, a cytotoxic nine-membered lactone isolated from the marine sponge Topsentia sp., were synthesized stereodivergently from a common chiral seco acid by the combined use of the Yamaguchi and Mitsunobu lactonizations. Comparison of the NMR spectra of the four diastereomers with those of an authentic sample of topsentolide C-2 led to the stereochemical determination of topsentolide C-2 as 8R, 11S, and 12S. (C) 2013 Elsevier Ltd. All rights reserved.