hex-5-en-1-yn-3-ol | 116182-59-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hex-5-en-1-yn-3-ol
• 英文别名: Allylpropargyl alcohol
• CAS: 116182-59-3
• 化学式: C₆H₈O
• 分子量: 96.1289
• InChiKey: HRTFZVSJWXOSIX-UHFFFAOYSA-N

物化性质

• 沸点：
  148.4±20.0 °C(Predicted)
• 密度：
  0.921±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  hex-5-en-1-yn-3-ol 在 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 94.25h， 生成 5-[tert-butyl(dimethyl)silyl]oxyoct-7-en-3-yn-1-ol
  参考文献：
  名称：

  Design of a radical translocation step through 1, n (n = 5, 6, 7) hydrogen transfers for incorporation into new radical cascades

  摘要：

  The scope and limitations in the 1,n (n = 5, 6, 7) hydrogen transfers from homoallyl radicals of type 10 have been delineated. Encouraging results have notably been obtained with a dioxolane on the side chain to promote a 1,6-H transfer and with a TBS ether to promote a 1,5-H transfer. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00899-5
• 作为产物：
  描述：

  (+/-)-1-(trimethylsilyl)hex-5-en-1-yn-3-ol 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 hex-5-en-1-yn-3-ol
  参考文献：
  名称：

  Metathesis in the presence of a transition metal alkyne complex

  摘要：

  A ring closing metathesis approach to medium sized rings is described. The methodology succeeds in the presence of a transition metal alkyne complex. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01017-6

文献信息

• Highly Regio- and Stereoselective Halohydroxylation Reaction of 1,2-Allenyl Phenyl Sulfoxides. Reaction Scope, Mechanism, and the Corresponding Pd- or Ni-Catalyzed Selective Coupling Reactions
  作者：Shengming Ma、Hongjun Ren、Qi Wei

  DOI：10.1021/ja034039q

  日期：2003.4.1

  A highly regio- and stereoselective halohydroxylation of 1,2-allenyl sulfoxides with X(+) and water was developed. The reaction shows E-stereoselectivity. In the iodohydroxylation reaction, I(2) was used to introduce the iodine atom. For bromohalohydroxylation, CuBr(2), NBS, or Br(2) can be used. When using I(2), NBS, or Br(2), the addition of LiOAc.2H(2)O is necessary for high yields of the halohydroxylation

  开发了 1,​​2-烯基亚砜与 X(+) 和水的高度区域和立体选择性卤代羟基化。该反应显示出 E-立体选择性。在碘羟基化反应中，I(2) 用于引入碘原子。对于溴卤羟基化，可以使用 CuBr(2)、NBS 或 Br(2)。当使用 I(2)、NBS 或 Br(2) 时，LiOAc.2H(2)O 的添加对于卤代羟基化产品的高产率是必要的。氯羟基化反应是通过用硅胶研磨 1,2-烯基亚砜和 CuCl(2).2H(2)O 来进行的。在 Pd(0) 配合物的催化下，卤代羟基化产物，即 E-2-halo-1-phenylsulfinyl-1-alken-3-ols，可以发生 Sonogashira、Suzuki 和 Negishi 交叉偶联反应，导致Z-2-取代的-1-苯基磺酰基-1-链烯-3-醇。偶联产物的CS键可以在Ni催化剂的催化下与有机锌进一步发生偶联反应。在这里，羟基的存在对于涉及 CS 键的平
• Chemoselective Epoxidation of Ene-Ynamides: Intramolecular Cyclopropanation Induced by the Intermediate α-Oxocarbene
  作者：Christophe Meyer、Sylvain Couty、Janine Cossy

  DOI：10.1055/s-2007-990841

  日期：——

  Chemoselective epoxidation of the triple bond of ene-ynamides generates an α-oxocarbene intermediate that effects the intramolecular cyclopropanation of the alkene.

  烯-炔酰胺三键的化学选择性环氧化反应会产生δ-氧代碳中间体，从而影响烯的分子内环丙烷化反应。
• The influence of intramolecular dynamics on branching ratios in thermal rearrangements
  作者：Richard H. Newman-Evans、Reyna J. Simon、Barry K. Carpenter

  DOI：10.1021/jo00289a053

  日期：1990.1
• Enantioselective hydrolyses by baker's yeast - III11For part II Bee; B.I. Glänzer, K. Faber and H. Griengl, Tetrahedron 43, 771 (1987).
  作者：B.I. Glänzer、K. Faber、H. Griengl

  DOI：10.1016/s0040-4020(01)87785-1

  日期：——
• Radical cyclization of (bromomethyl)dimethylsilyl propargyl ethers. Regio-, chemo- and stereoselectivity.
  作者：Michel Journet、Max Malacria

  DOI：10.1021/jo00037a026

  日期：1992.5

  Radical cyclization of (bromomethyl)dimethylsilyl propargyl ether derivatives 1 is a powerful reaction with a high degree of regio-, chemo-, and stereoselectivity. Trisubstituted olefins 3, cyclopentene derivatives 5, and diquinane system 7j are obtained in good yields by a judicious choice of unsaturated substituents. Triquinane frameworks could be obtained stereoselectively from a suitable acyclic substrate of type 1 in a one-pot reaction. First attempts have not yet allowed us to aim at this goal due to interesting (1,5) hydrogen transfers. Moreover, we have intercepted, for the first time, the alpha-cyclopropyl radical which is involved in the Stork-Beckwith mechanism of the 5-versus 6-membered ring formation in the vinyl radical cyclization.