(4S)-4-ethyl-2-hydroxy-3-methyl-5-methylidenecyclopent-2-en-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S)-4-ethyl-2-hydroxy-3-methyl-5-methylidenecyclopent-2-en-1-one
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: WNERXFHNBQDTMS-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 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：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-methyl-1-morpholin-4-ylpent-2-en-1-one 、 1-O-allenyl-3,4,6-tri-O-t-butyldimethylsilyl-2-deoxy-α-D-glucopyranoside 在 盐酸 正丁基锂 、 1,10-菲罗啉 、 lithium chloride 、 六氟异丙醇 、 乙酰氯 作用下， 以 四氢呋喃 、 正己烷 、 2,2,2-三氟乙醇 为溶剂， 反应 2.75h， 生成 (4S)-4-ethyl-2-hydroxy-3-methyl-5-methylidenecyclopent-2-en-1-one 、 (4R)-4-ethyl-2-hydroxy-3-methyl-5-methylidenecyclopent-2-en-1-one
  参考文献：
  名称：

  An Improved Chiral Auxiliary for the Allene Ether Version of the Nazarov Cyclization

  摘要：

  alpha-2-Deoxy-D-glucose derived ether 14 is a superior reagent for the allene ether version of the Nazarov cyclization. Enantiomeric excesses of products derived from trisubstituted morpholino enamides varied between 85% and 93% ee.

  DOI：

  10.1021/ol060816q

文献信息

• Asymmetric Cyclopentannelation:  Camphor-Derived Auxiliary
  作者：Paul E. Harrington、Tsuyoshi Murai、Chester Chu、Marcus A. Tius

  DOI：10.1021/ja020591o

  日期：2002.8.1

  The scope of an enantioselective cyclopentannelation reaction that makes use of allenyl ether-derived nucleophiles has been probed. The enantioselectivity is induced by a traceless chiral auxiliary that is easily derived from camphor. It has been shown that for gamma-substituted allene ethers that are axially chiral, very high enantiomeric excesses of cyclopentenone products are observed in the matched cases. Two fundamentally different mechanisms are observed, one for the cyclizations of allenyl ketones (see eq 7), the other for the cyclizations of allenyl alcohols (see eq 11). The methodology is versatile, efficient, and well-suited for applications in synthesis.
• An Improved Chiral Auxiliary for the Allene Ether Version of the Nazarov Cyclization
  作者：Derrick B. delos Santos、April R. Banaag、Marcus A. Tius

  DOI：10.1021/ol060816q

  日期：2006.6.1

  alpha-2-Deoxy-D-glucose derived ether 14 is a superior reagent for the allene ether version of the Nazarov cyclization. Enantiomeric excesses of products derived from trisubstituted morpholino enamides varied between 85% and 93% ee.