1-phenyl-2-propyl-3-butyn-1-ol | 319923-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-phenyl-2-propyl-3-butyn-1-ol
• 英文别名: 1-phenyl-2-propyl-but-3-yn-1-ol；Opt.-inakt. 1-Hydroxy-2-aethinyl-1-phenyl-pentan；1-Phenyl-2-propyl-but-3-in-1-ol；2-Ethynyl-1-phenylpentan-1-ol
• CAS: 319923-38-1
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: OWVPSTMOOUWGTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  1-phenyl-2-propyl-3-butyn-1-ol 在 硫酸 、 mercury(II) sulfate 作用下， 生成 2-propyl-1-phenyl-buten-(1)-one-(3) 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  569.炔类化合物的研究。第二十一部分。用炔丙基溴进行Reformatsky反应

  摘要：

  DOI：

  10.1039/jr9490002696
• 作为产物：
  描述：

  1-己炔-3-醇 在 chromium dichloride 、 氢氧化钾 、 lithium bromide 作用下， 以 乙醚 、 N,N-二甲基乙酰胺 、 二甲基亚砜 为溶剂， 反应 2.5h， 生成 1-phenyl-2-propyl-3-butyn-1-ol
  参考文献：
  名称：

  Preparation of polyfunctional allenic alcohols by the regioselective addition of functionalized propargylic chromium(III) organometallics to carbonyl compounds

  摘要：

  The reaction of propargylic halides 1 (X = Cl, Br) with an aldehyde or ketone (0.67 equiv) in the presence of CrCl2 (2.0 equiv) and LiI (2 equiv, necessary if X = Cl) affords allenic alcohols 3 with excellent regioselectivities (3-6% of the regioisomeric acetylenic alcohol 4 is formed) and in good yields (68-90%). Interestingly, this method allows the generation of highly functionalized intermediate propargylic chromium organometallics contained an ester, cyano, or chloride functionality. The alpha-alkyl-substituted propargylic bromide 10 reacts with benzaldehyde yielding the acetylenic alcohol 11 as a diastereomeric mixture of only one regioisomer (90% yield).

  DOI：

  10.1021/jo00041a006

文献信息

• Carbonyl Allenylations andPropargylations by 3-Chloro-1-propyne or 2-Propynyl Mesylateswith Tin(IV) Chloride and Tetrabutylammonium Iodide
  作者：Yoshiro Masuyama、Akiko Watabe、Yasuhiko Kurusu

  DOI：10.1055/s-2003-41012

  日期：——

  By the use of tin(IV) chloride and tetrabutylammonium iodidein dichloromethane, 3-chloro-1-propyne or 2-propynyl mesylate canbe applied to allenylation and propargylation of aldehydes (carbonylallenylation and propargylation) to produce a mixture of 1-substituted2,3-butadien-1-ols and 1-substituted 3-butyn-1-ols. 1-Substituted2-propynyl mesylates selectively cause carbonyl propargylation,while 3-substituted 2-propynyl mesylates cause carbonyl allenylation.

  通过使用四氯化锡和四丁基碘化铵在二氯甲烷中，3-氯-1-丙炔或2-丙炔基甲磺酸酯可用于醛的烯丙炔化（碳基烯丙炔化和丙炔化），产生1-取代的2,3-丁二烯-1-醇和1-取代的3-丁炔-1-醇的混合物。1-取代的2-丙炔基甲磺酸酯选择性地导致碳基丙炔化，而3-取代的2-丙炔基甲磺酸酯导致碳基烯丙炔化。
• 569. Researches on acetylenic compounds. Part XXI. Reformatsky reactions with propargyl bromides
  作者：H. B. Henbest、E. R. H. Jones、I. M. S. Walls

  DOI：10.1039/jr9490002696

  日期：——
• Preparation of polyfunctional allenic alcohols by the regioselective addition of functionalized propargylic chromium(III) organometallics to carbonyl compounds
  作者：Kevin Belyk、Michael J. Rozema、Paul Knochel

  DOI：10.1021/jo00041a006

  日期：1992.7

  The reaction of propargylic halides 1 (X = Cl, Br) with an aldehyde or ketone (0.67 equiv) in the presence of CrCl2 (2.0 equiv) and LiI (2 equiv, necessary if X = Cl) affords allenic alcohols 3 with excellent regioselectivities (3-6% of the regioisomeric acetylenic alcohol 4 is formed) and in good yields (68-90%). Interestingly, this method allows the generation of highly functionalized intermediate propargylic chromium organometallics contained an ester, cyano, or chloride functionality. The alpha-alkyl-substituted propargylic bromide 10 reacts with benzaldehyde yielding the acetylenic alcohol 11 as a diastereomeric mixture of only one regioisomer (90% yield).