(E)-4-hydroxy-3-(hydroxymethyl)-4-(prop-1-enyl)tetrahydro-2H-pyran-2-one | 1375003-54-5

• 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: (E)-4-hydroxy-3-(hydroxymethyl)-4-(prop-1-enyl)tetrahydro-2H-pyran-2-one
• 英文别名: 4-hydroxy-3-(hydroxymethyl)-4-[(E)-prop-1-enyl]oxan-2-one
• CAS: 1375003-54-5
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: YUWJDOZTOBTXJF-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-hydroxy-3-(hydroxymethyl)-4-(prop-1-enyl)tetrahydro-2H-pyran-2-one 在 碳酸氢钠 、 戴斯-马丁氧化剂 、 二乙胺 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 19.5h， 生成 angelone
  参考文献：
  名称：

  Total synthesis of angelone enabled by a remarkable biomimetic sequence

  摘要：

  The natural product angelone was readily accessed with a remarkable biomimetic journey that sequentially features carbonyl formation elimination, 6 pi-electrocyclization, visible light-promoted singlet O-2 Diels-Alder reaction, Kornblum-DeLaMare-type peroxide rearrangement, 6 pi-electrocyclic ring-opening, and conjugative addition-elimination as the key steps. With key intermediates isolated and characterized, this study stands to reveal a rare system in which bio-inspired synthetic strategies were found to mirror experimental realities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.076
• 作为产物：
  描述：

  (E)-1,3-dihydroxyhex-4-ene 在 咪唑 、 甲醇 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 80.33h， 生成 (E)-4-hydroxy-3-(hydroxymethyl)-4-(prop-1-enyl)tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Total synthesis of angelone enabled by a remarkable biomimetic sequence

  摘要：

  The natural product angelone was readily accessed with a remarkable biomimetic journey that sequentially features carbonyl formation elimination, 6 pi-electrocyclization, visible light-promoted singlet O-2 Diels-Alder reaction, Kornblum-DeLaMare-type peroxide rearrangement, 6 pi-electrocyclic ring-opening, and conjugative addition-elimination as the key steps. With key intermediates isolated and characterized, this study stands to reveal a rare system in which bio-inspired synthetic strategies were found to mirror experimental realities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.076

文献信息

• Total synthesis of angelone enabled by a remarkable biomimetic sequence
  作者：Haibo Tan、Xinzheng Chen、Zheng Liu、David Zhigang Wang

  DOI：10.1016/j.tet.2012.03.076

  日期：2012.5

  The natural product angelone was readily accessed with a remarkable biomimetic journey that sequentially features carbonyl formation elimination, 6 pi-electrocyclization, visible light-promoted singlet O-2 Diels-Alder reaction, Kornblum-DeLaMare-type peroxide rearrangement, 6 pi-electrocyclic ring-opening, and conjugative addition-elimination as the key steps. With key intermediates isolated and characterized, this study stands to reveal a rare system in which bio-inspired synthetic strategies were found to mirror experimental realities. (C) 2012 Elsevier Ltd. All rights reserved.