(1R,2R)-2-(6-oxooxan-2-yl)cyclopropane-1-carbaldehyde | 148138-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,2R)-2-(6-oxooxan-2-yl)cyclopropane-1-carbaldehyde
• CAS: 148138-16-3
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: BJLRZRBGFHEVOW-KJFJCRTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  Aplydilactone 在 platinum(IV) oxide 吡啶 、 sodium periodate 、 四氧化锇 、 氢气 作用下， 生成 (1R,2R)-2-(6-oxooxan-2-yl)cyclopropane-1-carbaldehyde
  参考文献：
  名称：

  Aplydilactone, a novel fatty acid metabolite from the marine mollusc aplysia kurodai

  摘要：

  DOI：

  10.1016/s0040-4039(00)97765-7

文献信息

• Cyclopropane-Containing Eicosanoids of Marine Origin. Biomimetic Synthesis of Constanolactones A and B from the Alga Constantinea simplex
  作者：James D. White、Mark S. Jensen

  DOI：10.1021/ja00128a008

  日期：1995.6

  Asymmetric syntheses of 7, a substance isolated from incubation of arachidonic acid with an acetone powder of the coral Plexaura homomalla, and of constanolactones A (9) and B (10), metabolites of the red alga Constantinea simplex, are described. The key step involves stannic chloride-mediated cyclization of the oxirane derived from Sharpless epoxidation of 10-hydroxy-5,8-decadienoates, and is shown to yield a trans disubstituted cyclopropane Linked to a delta-lactone. Both (R) and (S) configurations at C5 of the lactone are produced in the cyclization, the ratio being independent of olefin geometry in the acyclic precursor, Elaboration of the cyclization products via Nozaki-Kishi coupling of the derived aldehydes 26 and 37 with the appropriate (1E,5Z)-1-iodo-1,5-undecadiene led to 7, 9, and 10, thereby establishing the relative configuration of 7 and confirming the absolute configuration of 9 and 10.