neohalicholactone | 124190-21-2

• 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: neohalicholactone
• 英文别名: (2S,4Z)-2-[(1R,2R)-2-[(1R,2E,4R,6Z)-1,4-dihydroxynona-2,6-dienyl]cyclopropyl]-3,6,7,8-tetrahydro-2H-oxonin-9-one
• CAS: 124190-21-2
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: BTDSTEQIFQUGOV-RUHIXKDASA-N

物化性质

• 熔点：
  72 °C
• 沸点：
  531.9±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1R,2R)-2-((Z)-(S)-9-Oxo-2,3,6,7,8,9-hexahydro-oxonin-2-yl)-cyclopropanecarboxylic acid 在 chromium chloride 、 sodium tetrahydroborate 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 四丁基氟化铵 、 nickel dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.33h， 生成 neohalicholactone
  参考文献：
  名称：

  Total Synthesis of Halicholactone and Neohalicholactone¹

  摘要：

  The total synthesis of the marine natural products neohalicholactone (1) and halicholactone (2), in enantiomerically pure form, are reported. Key steps in the synthesis of each compound include a cis-selective Wittig reaction, stereoselective cyclopropanation, nine-membered lactone formation using the Yamaguchi method and late-stage stereoselective Cr(II)/Ni(II) mediated coupling of vinyl iodides 39 and 50 with aldehyde 14. In the case of the neohalicholactone synthesis the two major components which were coupled in this convergent synthesis were each derived from the enantiomers of commercially available malic acid. The synthesis served to confirm the original assignment of absolute configuration which was made by Yamada and Clardy. We also demonstrated, through the preparation of diastereoisomers, that another reported compound closely related to neohalicholactone is likely to be the C-15 epimer 67.

  DOI：

  10.1021/jo962312j

文献信息

• Total Synthesis of Halicholactone and Neohalicholactone
  作者：Jörg Pietruszka、Martina Bischop、Verena Doum、Anja Nordschild née Rieche、Diana Sandkuhl

  DOI：10.1055/s-0029-1217145

  日期：2010.2

  New total syntheses of the marine oxylipins halicholactone and neohalicholactone are presented. The key building blocks were synthesized utilizing chemoenzymatic methods. natural product - total synthesis - enzymes - boron reagents - asymmetric synthesis

  提出了新的海洋氧合素卤代内酯 和新卤代内酯的合成方法 。关键组成部分是利用化学酶法合成的。 天然产物-全合成-酶-硼试剂-不对称合成
• The total asymmetric synthesis of Halicholactone and Neohalicholactone
  作者：Douglas J. Critcher、Stephen Connolly、Martin Wills

  DOI：10.1016/0040-4039(95)00588-4

  日期：1995.5

  Completion of the first total synthesis of the marine natural products Halicholactone and Neohalicholactone is reported. The key step is a moderately stereoselective coupling between a vinylic anion and an aldehyde. An unexpectedly slow desilylation due to the presence of a proximal hydroxy group is also reported.

  据报道已经完成了海洋天然产物卤代内酯和新卤代内酯的第一个全合成反应。关键步骤是乙烯基阴离子和醛之间的中等立体选择性偶联。还报道了由于近端羟基的存在而出乎意料的缓慢的甲硅烷基化。
• Total Synthesis of Halicholactone and Neohalicholactone¹
  作者：Douglas J. Critcher、Stephen Connolly、Martin Wills

  DOI：10.1021/jo962312j

  日期：1997.9.1

  The total synthesis of the marine natural products neohalicholactone (1) and halicholactone (2), in enantiomerically pure form, are reported. Key steps in the synthesis of each compound include a cis-selective Wittig reaction, stereoselective cyclopropanation, nine-membered lactone formation using the Yamaguchi method and late-stage stereoselective Cr(II)/Ni(II) mediated coupling of vinyl iodides 39 and 50 with aldehyde 14. In the case of the neohalicholactone synthesis the two major components which were coupled in this convergent synthesis were each derived from the enantiomers of commercially available malic acid. The synthesis served to confirm the original assignment of absolute configuration which was made by Yamada and Clardy. We also demonstrated, through the preparation of diastereoisomers, that another reported compound closely related to neohalicholactone is likely to be the C-15 epimer 67.