6-甲基-6-庚烯-4-炔-3-醇 | 95764-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-甲基-6-庚烯-4-炔-3-醇
• 英文名称: 6-methyl-6-hepten-4-yn-3-ol
• 英文别名: 6-methylhept-6-en-4-yn-3-ol
• CAS: 95764-76-4
• 化学式: C₈H₁₂O
• mdl: MFCD00041590
• 分子量: 124.183
• InChiKey: DUDZQARPXNGCOB-UHFFFAOYSA-N

物化性质

• 沸点：
  87°C 14mm
• 保留指数：
  972

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险类别码：
  R36/37/38
• 海关编码：
  2905290000
• 安全说明：
  S26,S36/37/39

反应信息

• 作为反应物：
  描述：

  6-甲基-6-庚烯-4-炔-3-醇 在 4-二甲氨基吡啶 、 三乙胺 、 copper(I) bromide 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.17h， 生成 3-ethyl-2-methylhepta-1,3,4-triene
  参考文献：
  名称：

  通过乙烯基丙烯烯和磺酰基氰化物的[4 + 2]环加成反应合成高度取代的吡啶。

  摘要：

  描述了合成多取代吡啶的收敛策略。乙烯基烯与Diels-Alder环加成物中的市售芳基磺酰基氰化物结合，生成异吡啶环加成物，其在进一步加热或添加碱后转化为吡啶。2-磺酰吡啶产物与氧和碳亲核试剂进行亲核芳族取代反应，以提供进入各种高度取代的吡啶的途径。

  DOI：

  10.1021/acs.joc.9b02628
• 作为产物：
  描述：

  丙醛 、 9-(3-Methylbut-3-en-1-yn-1-yl)-9-borabicyclo[3.3.1]nonane 在 C.I.酸性橙108 作用下， 以 正戊烷 为溶剂， 反应 0.5h， 以81%的产率得到6-甲基-6-庚烯-4-炔-3-醇
  参考文献：
  名称：

  Organoboranes. 38. A facile and highly efficient addition of B-1-alkynyl-9-borabicyclo[3.3.1]nonanes to aldehydes and ketones: an exceptionally chemoselective synthesis of propargylic alcohols

  摘要：

  DOI：

  10.1021/jo00210a003

文献信息

• Ene-yne unsaturated compounds as accelerators for hydrosilation
  申请人：DOW CORNING CORPORATION

  公开号：EP0751140A2

  公开（公告）日：1997-01-02

  A hydrosilation process where a silicon hydride is reacted with an unsaturated reactant in the presence of a platinum catalyst and an accelerator selected from ene-yne unsaturated compounds. The accelerators are especially useful for facilitating the hydrosilation of unsaturated reactants where the unsaturation is in the internal portion of the reactant's structure, for example, as in cyclopentene or cyclohexene.

  一种氢化硅在铂催化剂和选自烯炔不饱和化合物的促进剂存在下与不饱和反应物反应的氢化工艺。促进剂特别适用于促进不饱和反应物的加氢反应，不饱和反应物的不饱和结构位于反应物结构的内部，例如环戊烯或环己烯。
• Diastereoselective [4 + 1] Cycloaddition of Alkenyl Propargyl Acetates with CO Catalyzed by [RhCl(CO)₂]₂
  作者：Wei Chen、Jia-Hui Tay、Xiao-Qi Yu、Lin Pu

  DOI：10.1021/jo3009403

  日期：2012.7.20

  A class of alkenyl propargyl acetates, RCH(OAc)C CC(CH3)=CH2 (5), are found to undergo [4 + 1] cycloaddition with CO (1 atm) in the presence of [RhCl(CO)(2)](2) in refluxing 1,2-dichloroethane to give cyclopentenones (6) in good yields. It has been demonstrated that, when the R group of 5 is a phenyl group bearing o-electron-withdrawing substituents up to 10:1 diastereoselectivity and 96% yield can be achieved for the [4 + 1] cycloaddition. This process provides a convenient method to construct highly functionalized cyclopentenones that are useful in organic synthesis.
• Nonenzymatic Kinetic Resolution of Propargylic Alcohols by a Planar−Chiral DMAP Derivative:  Crystallographic Characterization of the Acylated Catalyst
  作者：Beata Tao、J. Craig Ruble、Diego A. Hoic、Gregory C. Fu

  DOI：10.1021/ja9906958

  日期：1999.6.1
• Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp
  作者：Kevin Burgess、Lee D. Jennings

  DOI：10.1021/ja00016a032

  日期：1991.7

  Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of beta-hydroxy-alpha-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of gamma-hydroxy-alpha,beta-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.
• BROWN, H. C.;MOLANDER, G. A.;SINGH, SHANKAR, M.;RACHERLA, U. S., J. ORG. CHEM., 1985, 50, N 10, 1577-1582
  作者：BROWN, H. C.、MOLANDER, G. A.、SINGH, SHANKAR, M.、RACHERLA, U. S.

  DOI：——

  日期：——

表征谱图