(R,E)-(1-(prop-2-ynyloxy)but-2-enyl)cyclohexane | 1017246-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R,E)-(1-(prop-2-ynyloxy)but-2-enyl)cyclohexane
• 英文别名: [(E,1R)-1-prop-2-ynoxybut-2-enyl]cyclohexane
• CAS: 1017246-18-2
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: JDAXYJNAPYAUOK-UTPRNQHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R,E)-(1-(prop-2-ynyloxy)but-2-enyl)cyclohexane 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 以93%的产率得到(3S,4S,E)-6-cyclohexyl-4-methylhex-5-en-1-yn-3-ol
  参考文献：
  名称：

  Asymmetric Catalysis Route to anti,anti Stereotriads, Illustrated by Applications

  摘要：

  A short sequence based on asymmetric catalysis, chirality transfer, and an optimized carbometallation protocol gave an anti,anti stereotriad building block in six steps. Both enantiomers of the chirality source, N-methyl ephedrine, are inexpensive, and the auxiliary is recoverable. In one chiral series, the building block was converted to the "B-2" intermediate in Miyashita's synthesis of scytophycin C; in the enantiomeric series, it was converted to a key intermediate for aplyronine A and to the polyketide "cap" for the callipeltins.

  DOI：

  10.1021/ol702989g
• 作为产物：
  描述：

  (R,E)-1-cyclohexylbut-2-en-1-ol 、 3-溴丙炔 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到(R,E)-(1-(prop-2-ynyloxy)but-2-enyl)cyclohexane
  参考文献：
  名称：

  Asymmetric Catalysis Route to anti,anti Stereotriads, Illustrated by Applications

  摘要：

  A short sequence based on asymmetric catalysis, chirality transfer, and an optimized carbometallation protocol gave an anti,anti stereotriad building block in six steps. Both enantiomers of the chirality source, N-methyl ephedrine, are inexpensive, and the auxiliary is recoverable. In one chiral series, the building block was converted to the "B-2" intermediate in Miyashita's synthesis of scytophycin C; in the enantiomeric series, it was converted to a key intermediate for aplyronine A and to the polyketide "cap" for the callipeltins.

  DOI：

  10.1021/ol702989g

文献信息

• Asymmetric Catalysis Route to <i>anti</i>,<i>anti</i> Stereotriads, Illustrated by Applications
  作者：Kathlyn A. Parker、Qiuzhe Xie

  DOI：10.1021/ol702989g

  日期：2008.4.1

  A short sequence based on asymmetric catalysis, chirality transfer, and an optimized carbometallation protocol gave an anti,anti stereotriad building block in six steps. Both enantiomers of the chirality source, N-methyl ephedrine, are inexpensive, and the auxiliary is recoverable. In one chiral series, the building block was converted to the "B-2" intermediate in Miyashita's synthesis of scytophycin C; in the enantiomeric series, it was converted to a key intermediate for aplyronine A and to the polyketide "cap" for the callipeltins.