(5S)-5-(3-Iodo-2-methylprop-2-en-1-yl)oxolan-2-one | 404356-75-8

• 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: (5S)-5-(3-Iodo-2-methylprop-2-en-1-yl)oxolan-2-one
• 英文别名: (5S)-5-(3-iodo-2-methylprop-2-enyl)oxolan-2-one
• CAS: 404356-75-8
• 化学式: C₈H₁₁IO₂
• 分子量: 266.079
• InChiKey: MDYGEDSNYRWBAY-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯基溴化硒 、 (5S)-5-(3-Iodo-2-methylprop-2-en-1-yl)oxolan-2-one 在 lithium hexamethyldisilazane 、 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 、
  参考文献：
  名称：

  A strategy toward the synthesis of C13-oxidized cembrenolides

  摘要：

  An efficient strategy for the construction of C-13-oxidized cembrenolides is reported. Central to this strategy is the installation of the C-13 hydroxyl group prior to cembrane macrocyclization (via formation of the C-1-C-2 bond), allowing access to both C-13 alcohol epimers. The orientation of the C-13 alcohol was found to influence the cyclization mode of the cembranolide scaffold upon furan oxidation, leading to motifs reminiscent to bipinnatolide F, bielschowskysin, and verrillin. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.085
• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 0.5h， 以0.37 g的产率得到(5S)-5-(3-Iodo-2-methylprop-2-en-1-yl)oxolan-2-one
  参考文献：
  名称：

  A strategy toward the synthesis of C13-oxidized cembrenolides

  摘要：

  An efficient strategy for the construction of C-13-oxidized cembrenolides is reported. Central to this strategy is the installation of the C-13 hydroxyl group prior to cembrane macrocyclization (via formation of the C-1-C-2 bond), allowing access to both C-13 alcohol epimers. The orientation of the C-13 alcohol was found to influence the cyclization mode of the cembranolide scaffold upon furan oxidation, leading to motifs reminiscent to bipinnatolide F, bielschowskysin, and verrillin. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.085

文献信息

• A strategy toward the synthesis of C13-oxidized cembrenolides
  作者：Alec Saitman、Steven D.E. Sullivan、Emmanuel A. Theodorakis

  DOI：10.1016/j.tetlet.2013.01.085

  日期：2013.3

  An efficient strategy for the construction of C-13-oxidized cembrenolides is reported. Central to this strategy is the installation of the C-13 hydroxyl group prior to cembrane macrocyclization (via formation of the C-1-C-2 bond), allowing access to both C-13 alcohol epimers. The orientation of the C-13 alcohol was found to influence the cyclization mode of the cembranolide scaffold upon furan oxidation, leading to motifs reminiscent to bipinnatolide F, bielschowskysin, and verrillin. (c) 2013 Elsevier Ltd. All rights reserved.