(1S,2S)-2-((Z)-(S)-7-Carboxy-1-hydroxy-hept-3-enyl)-cyclopropanecarboxylic acid tert-butyl ester | 194540-68-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (1S,2S)-2-((Z)-(S)-7-Carboxy-1-hydroxy-hept-3-enyl)-cyclopropanecarboxylic acid tert-butyl ester
• CAS: 194540-68-6
• 化学式: C₁₆H₂₆O₅
• 分子量: 298.379
• InChiKey: SIGOSGQXKVQWMV-DCRFLDTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-((Z)-(S)-7-Carboxy-1-hydroxy-hept-3-enyl)-cyclopropanecarboxylic acid tert-butyl ester 在 4-二甲氨基吡啶 、 三氟甲磺酸 、 2,4,6-三氯苯甲酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.5h， 生成 (1S,2S)-2-((Z)-(S)-9-Oxo-2,3,6,7,8,9-hexahydro-oxonin-2-yl)-cyclopropanecarboxylic acid
  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
• 作为产物：
  描述：

  (1S,2S)-2-((Z)-(S)-1-Hydroxy-7-methoxycarbonyl-hept-3-enyl)-cyclopropanecarboxylic acid tert-butyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 16.0h， 以100%的产率得到(1S,2S)-2-((Z)-(S)-7-Carboxy-1-hydroxy-hept-3-enyl)-cyclopropanecarboxylic acid tert-butyl ester
  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