(S)-2-allyl-4-hydroxycyclohex-2-enone | 1005488-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-allyl-4-hydroxycyclohex-2-enone
• 英文别名: (4S)-2-allyl-4-hydroxycyclohex-2-en-1-one；(4S)-4-hydroxy-2-prop-2-enylcyclohex-2-en-1-one
• CAS: 1005488-25-4
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: WDRCIJYKQSTHKP-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-allyl-4-hydroxycyclohex-2-enone 、 (S)-3-oxo-3-(pent-4-en-2-yloxy)propanoic acid 在 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 以85%的产率得到(S)-3-allyl-4-oxocyclohex-2-enyl (S)-pent-4-en-2-yl malonate
  参考文献：
  名称：

  A Convergent Synthesis of the Tricyclic Core of the Dictyosphaeric Acids

  摘要：

  The first synthetic route to the tricyclic core of the dictyosphaeric acids has been established starting from readily available (S)-(-)-4-(tert-butyldimethylsilyloxy)cyclohexenone and involving 9 steps, including a ring-closing metathesis to produce a 13-membered macrolactone, and a doubly tethered intramolecular Michael addition.

  DOI：

  10.1021/ol702887e
• 作为产物：
  描述：

  (S)-2-allyl-4-(tert-butyldimethylsilyloxy)cyclohex-2-enone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (S)-2-allyl-4-hydroxycyclohex-2-enone
  参考文献：
  名称：

  A Convergent Synthesis of the Tricyclic Core of the Dictyosphaeric Acids

  摘要：

  The first synthetic route to the tricyclic core of the dictyosphaeric acids has been established starting from readily available (S)-(-)-4-(tert-butyldimethylsilyloxy)cyclohexenone and involving 9 steps, including a ring-closing metathesis to produce a 13-membered macrolactone, and a doubly tethered intramolecular Michael addition.

  DOI：

  10.1021/ol702887e

文献信息

• Asymmetric synthesis of 2-alkyl-4-hydroxycyclohex-2-en-1-ones by scandium(III) triflate-catalyzed fragmentation of 2-alkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones
  作者：Jun-ichi Matsuo、Mizuki Kawano、Kosuke Takeuchi、Hiroyuki Tanaka、Hiroyuki Ishibashi

  DOI：10.1016/j.tetlet.2009.02.016

  日期：2009.4

  Fragmentation of (2S,3S,4S)-2-allyl-3-iodo-1-oxocyclohexan-2,4-carbolactone to (4S)-2-allyl-4-hydroxy-cyclohex-2-en-1-one, a chiral building block of (-)-platensimycin, proceeded efficiently by using scandium(III) triflate in DMF-H2O (1:3) at 100 degrees C. (C) 2009 Elsevier Ltd. All rights reserved.
• A Convergent Synthesis of the Tricyclic Core of the Dictyosphaeric Acids
  作者：Christopher W. Barfoot、Alan R. Burns、Michael G. Edwards、Martin N. Kenworthy、Mahmood Ahmed、Stephen E. Shanahan、Richard J. K. Taylor

  DOI：10.1021/ol702887e

  日期：2008.1.1

  The first synthetic route to the tricyclic core of the dictyosphaeric acids has been established starting from readily available (S)-(-)-4-(tert-butyldimethylsilyloxy)cyclohexenone and involving 9 steps, including a ring-closing metathesis to produce a 13-membered macrolactone, and a doubly tethered intramolecular Michael addition.