(3-hydroxy-1-cyclohexenyl)ethanenitrile | 105694-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-hydroxy-1-cyclohexenyl)ethanenitrile
• 英文别名: 2-(3-Hydroxycyclohexen-1-yl)acetonitrile
• CAS: 105694-74-4
• 化学式: C₈H₁₁NO
• 分子量: 137.181
• InChiKey: HEUPNGGZVYOSPX-UHFFFAOYSA-N

物化性质

• 沸点：
  272.8±33.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (7-oxabicyclo<4.1.0>hept-2-ylidene)ethanenitrile 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到(3-hydroxy-1-cyclohexenyl)ethanenitrile
  参考文献：
  名称：

  Reductive cleavage reaction of .gamma.-functionalized .alpha.,.beta.-unsaturated esters and halomethyls mediated with magnesium in methanol

  摘要：

  Reductive cleavage of various types of C-O and C-N bonds tethered to alpha,beta-unsaturated esters and halomethyls was mediated with magnesium in methanol, which provided a facile method for the synthesis of delta-hydroxy or delta-amino beta,gamma-unsaturated esters and allylic alcohols. Regardless of the geometry (E or Z) of the alpha,beta-unsaturated esters, 1a-b, 5a-c, 11, 13, and 23, the cleavage product obtained was exclusively the E isomer of the corresponding deconjugated hydroxy and amino esters. The steric bias and ring strain of 15, 17, and 21 gave rise to a product mixture of E and Z isomers.

  DOI：

  10.1021/jo00058a038

文献信息

• Lanthanides in organic synthesis. 5. Reduction of vinyloxiranes with samarium diiodide. An efficient route to functionalized chiral, non-racemic (E)-allylic alcohols
  作者：Gary A. Molander、Bruce E. La Belle、Gregory Hahn

  DOI：10.1021/jo00376a039

  日期：1986.12
• Pak Chwang Siek, Lee Eun, Lee Ge Hyeong, J. Org. Chem, 58 (1993) N 6, S 1523-1530
  作者：Pak Chwang Siek, Lee Eun, Lee Ge Hyeong

  DOI：——

  日期：——
• MOLANDER G. A.; LA BELLE B. E.; HAHN G., J. ORG. CHEM., 51,(1986) N 26, 5259-5264
  作者：MOLANDER G. A.、 LA BELLE B. E.、 HAHN G.

  DOI：——

  日期：——