3-methyl-pent-4-yn-1-ol | 55930-35-3

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 3-methyl-pent-4-yn-1-ol
• 英文别名: 3-Methylpent-4-yn-1-ol
• CAS: 55930-35-3
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: RRURBGUJFHZKAL-UHFFFAOYSA-N

物化性质

• 沸点：
  68-71 °C(Press: 24 Torr)
• 密度：
  0.898±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：
  0.67
• 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：

  3-methyl-pent-4-yn-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四溴化碳 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-(5-bromo-3-methylpent-1-ynyl)-4-nitrobenzene
  参考文献：
  名称：

  Modular and Stereoselective Synthesis of Tetrasubstituted Helical Alkenes via a Palladium-Catalyzed Domino Reaction

  摘要：

  A highly modular and stereoselective synthesis of tetrasubstituted helical alkenes is accomplished by a Pd-catalyzed norbornene-mediated domino reaction. This protocol features the rapid assembly of four C-C bonds via sequential C-H activations and carbopalladations along with efficient access to enantiopure bromoalkyl aryl alkyne precursors using homologative alkynylation as the key transformation. Three distinct elements of stereoselectivity were observed in the preparation of the chiral helical alkenes: retention of stereochemistry of the substrates, induced helical diastereoselectivity in the alkene formation, and the exclusive exo-facial selectivity of the norbornene incorporation.

  DOI：

  10.1021/ol301495q
• 作为产物：
  描述：

  α-甲基-γ-丁内酯 在 二异丁基氢化铝 、 (1-重氮基-2-氧代丙基)膦酸二甲酯 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 3-methyl-pent-4-yn-1-ol
  参考文献：
  名称：

  金 (I) 催化的丙炔双环化用于合成应变和平面多环化合物

  摘要：

  金催化的萘系联烯炔级联环化得到 4 H -环戊[ def ]菲 (CPP) 衍生物。该反应通过炔烃与活化丙二烯的亲核反应进行，生成乙烯基阳离子中间体，然后进行芳基化。还介绍了根据反应条件，使用芳基取代的底物选择性形成 CPP 和二苯并芴衍生物。

  DOI：

  10.1002/anie.202307532

文献信息

• Enäther als Reaktionspartner von Organometallen II Hydroxyäthyl-allene und andere Folgeprodukte aus Dihydrofuran-Derivaten
  作者：Bruno Schaub、Manfred Schlosser

  DOI：10.1002/hlca.19750580227

  日期：——

  with organolithium compounds, 2-alkyl-4,5-dihydrofurans undergo ring opening through β-elimination leading to the corresponding 3,4-dien-1-ol. If 3-chloro-2-methyl-4,5-dihydrofuran serves as a substrate, however, no 3-chloro-3,4-dien-1-ol can be isolated though it acts as a reaction intermediate. Its formation is slow compared to subsequent replacement of halogen by the organic moiety of the alkyllithium

  用有机锂化合物处理后，2-烷基-4,5-二氢呋喃通过β-消除进行开环反应，生成相应的3,4-二烯-1-醇。然而，如果将3-氯-2-甲基-4,5-二氢呋喃用作底物，则尽管其充当反应中间体，但不能分离出3-氯-3,4-二烯-1-醇。与随后被烷基锂试剂的有机部分取代卤素相比，其形成是缓慢的。因此形成五-3，4-二烯-1-醇，其可以异构化，但是在某些反应条件下提供末端乙炔。这些以及它们的烯丙基前体可以用氨中的钠转化为戊-4-烯-1-醇或戊-3-烯-1-醇衍生物。
• Relative Asymmetric Induction in the Intramolecular Reaction between Alkynes and Cyclopropylcarbene−Chromium Complexes:  Stereocontrolled Synthesis of Five-Membered Rings Fused to Oxygen Heterocycles
  作者：Jingbo Yan、Jin Zhu、Julius J. Matasi、James W. Herndon

  DOI：10.1021/jo982144q

  日期：1999.2.1

  Synthesis of cyclopentenone derivatives fused to oxygen heterocycles by means of the intramolecular coupling of alkynes and cyclopropylcarbene-chromium complexes has been examined for a variety of cases in which the tethering chain features a stereogenic center. In some cases, this process proceeds with a very high degree of stereoselectivity; however, the extent and direction of relative asymmetric induction is very dependent upon the position of the chiral atom within the tethering chain and the length of the tethering chain. In the best case, featuring a two-carbon tether and a stereogenic center at the homopropargylic position (complex 1N), the heterocyclic ring was produced with 97:3 selectivity for the cis heterocycle (3N). In the worst case, featuring a three-carbon tether and a stereogenic center at the homopropargylic position (complexes 1F and ii), no stereoselectivity was observed. Improvement in stereoselectivity was noticed when terminal alkynes were replaced by silylated alkynes and when proton sources were eliminated from the reaction.
• GIL, GERARD;FERRE, ELISEE;BARRE, MICHEL;LE, PETIT JEAN, TETRAHEDRON LETT., 29,(1988) N 31, C. 3797-3798
  作者：GIL, GERARD、FERRE, ELISEE、BARRE, MICHEL、LE, PETIT JEAN

  DOI：——

  日期：——