1-(but-3-yn-2-yl)cyclohexanol | 103934-07-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(but-3-yn-2-yl)cyclohexanol
• 英文别名: Cyclohexanol, 1-(1-methyl-2-propynyl)-；1-but-3-yn-2-ylcyclohexan-1-ol
• CAS: 103934-07-2
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: KHZPJGFUDYTAIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-Methyl-2-methylidene-1-oxaspiro[3.5]nonane 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到1-(but-3-yn-2-yl)cyclohexanol
  参考文献：
  名称：

  An Unanticipated Ring-Opening of 2-Methyleneoxetanes:  A Fundamentally New Approach to the Preparation of Homopropargylic Alcohols

  摘要：

  DOI：

  10.1021/jo9816360

文献信息

• Preparation of Organoaluminum Reagents from Propargylic Bromides and Aluminum Activated by PbCl2 and Their Regio- and Diastereoselective Addition to Carbonyl Derivatives
  作者：Li-Na Guo、Hongjun Gao、Peter Mayer、Paul Knochel

  DOI：10.1002/chem.201000523

  日期：2010.8.23

  propargylic and allenic aluminum reagents have been easily prepared by a direct insertion of aluminum into propargylic bromides in the presence of PbCl2 (1 mol %). These organoaluminum reagents react with carbonyl compounds to afford the corresponding allenic alcohols or homopropargylic alcohols in good to excellent yields with high regio‐ and diastereoselectivity.

  通过在PbCl 2（1 mol％）存在下将铝直接插入到炔丙基溴中，可以很容易地制备出各种炔丙基和烯丙基铝试剂。这些有机铝试剂可与羰基化合物反应，以高至极高的选择性和高非对映选择性提供相应的烯丙醇或均丙炔醇。
• A Highly Atom Efficient, Solvent Promoted Addition of Tetraallylic, Tetraallenic, and Tetrapropargylic Stannanes to Carbonyl Compounds
  作者：Adam McCluskey、I. Wayan Muderawan、Muntari、David J. Young

  DOI：10.1021/jo015904x

  日期：2001.11.1

  Tetraallylic, tetraallenic, and tetrapropargylic stannanes (0.25 equiv) react with aldehydes in methanol to provide unsaturated alcohols in good to excellent yields (56-99%). These reactions proceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)tin 16c and predominantly with allylic rearrangement for tetrapropadienyltin 16a and tetra(2-butynyl)tin 6e. Allylation. reactions also proceeded smoothly with reactive ketones such as ethyl pyruvate (9a) and cyclohexanone (9b). The corresponding TFA-catalyzed reactions of dimethyl acetals 4d and 4e are regiospecific with allylic rearrangement.
• An effective and selective conjugate propargylation reaction of stannylallenes to .alpha.,.beta.-unsaturated carbonyl compounds and .alpha.-nitro olefins
  作者：Junichi Haruta、Koichi Nishi、Satoshi Matsuda、Shuji Akai、Yasumitsu Tamura、Yasuyuki Kita

  DOI：10.1021/jo00303a019

  日期：1990.8
• An Unanticipated Ring-Opening of 2-Methyleneoxetanes:  A Fundamentally New Approach to the Preparation of Homopropargylic Alcohols
  作者：Lisa M. Dollinger、Amy R. Howell

  DOI：10.1021/jo9816360

  日期：1998.10.1