1-cyclopropyl-1-phenyl-3-butyn-1-ol | 91909-17-0

• 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-cyclopropyl-1-phenyl-3-butyn-1-ol
• 英文别名: 1-cyclopropyl-1-phenyl-but-3-yn-1-ol；1-Cyclopropyl-1-phenyl-but-3-in-1-ol；1-Cyclopropyl-1-phenylbut-3-yn-1-ol
• CAS: 91909-17-0
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: JYRPDXWBBUOQEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• 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：

  p-bromobenzenesulfonyl azide 、 1-cyclopropyl-1-phenyl-3-butyn-1-ol 在 噻吩-2-甲酸亚铜(I) 作用下， 以 甲苯 为溶剂， 以24%的产率得到2-(1-((4-bromophenyl)sulfonyl)-1H-1,2,3-triazol-4-yl)-1-cyclopropyl-1-phenylethan-1-ol
  参考文献：
  名称：

  通过 α-亚氨基铑卡宾的形成引发的 1,3-羟基迁移合成 α-氨基环丁酮

  摘要：

  实现了 α-亚氨基卡宾的正式分子内 1,3-OH 迁移，产生了独特的两性离子，随后的选择性环化提供了 α-氨基环丁酮。诸如易于获得的底物、温和的反应条件、省时的程序、出色的官能团兼容性和有价值的产品转化等特点使这一独特的协议成为合成应变环状化合物的有效工具。密度泛函理论计算与实验观察结果非常吻合，并提出了一个合理的机制。

  DOI：

  10.1021/acs.orglett.2c01029
• 作为产物：
  描述：

  丙二烯 、 苯基环丙基甲酮 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 3.0h， 生成 1-cyclopropyl-1-phenyl-3-butyn-1-ol
  参考文献：
  名称：

  钯催化的一氧化碳将醛和酮一氧化碳转化为4-取代的同炔丙基醇和5-En-3-yn-1-ols †

  摘要：

  用镁和正丁基锂顺序处理2,3-二氯丙烯产生了1,3-二硫代丙炔，这相当于向醛和酮的区域特异性添加，从而生成高炔丙醇。在钯催化下，可以按照此规程形成的乙炔化锂中间体与芳族卤化物和乙烯基卤化物进一步反应，分别在一个锅中以良好的纯度分别生成4-取代的炔丙基醇和5-en-3-yn-1-醇。整体产量。

  DOI：

  10.1021/acs.joc.7b01529

文献信息

• Propargylation of carbonyl compounds: An efficient method for the synthesis of homopropargyl alcohols
  作者：Jorge A. Cabezas、Leonardo X. Alvarez

  DOI：10.1016/s0040-4039(98)00727-8

  日期：1998.6

  Controlled dilithiation of allene, with two equivalents of n-butyllithium, produces the propargyl dianion 5. The latter couples efficiently with carbonyl compounds to produce homopropargyl alcohols in high yields.

  用两个当量的正丁基锂对丙二烯进行受控的二锂化，生成炔丙基二阴离子5。后者与羰基化合物有效偶联，以高收率生产高炔丙醇。
• Efficient Propargylation of Aldehydes and Ketones Catalyzed by Titanocene(III)
  作者：José Justicia、Iris Sancho-Sanz、Enrique Álvarez-Manzaneda、J. Enrique Oltra、Juan M. Cuerva

  DOI：10.1002/adsc.200900479

  日期：2009.10

  We describe a novel method for the propargylation of a wide range of aldehydes and ketones catalyzed by titanocene(III) complexes under mild reaction conditions and compatible with many functional groups. Homopropargylic alcohols are obtained as the sole products even when ketones are used as starting materials, which is unusual in Barbier-type propargylations.

  我们描述了一种新型方法，该方法用于在温和的反应条件下并与许多官能团相容，由钛茂（III）配合物催化广泛的醛和酮的炔丙基化。即使使用酮作为起始原料，也只能得到同炔丙醇，这在巴比尔型炔丙基化中是不常见的。
• A new method for the preparation of 1,3-dilithiopropyne: an efficient synthesis of homopropargyl alcohols
  作者：Jorge A Cabezas、Albán R Pereira、Adam Amey

  DOI：10.1016/s0040-4039(01)01429-0

  日期：2001.9

  propargyl bromide with two equivalents of n-butyllithium, in the presence of TMEDA, produces the operational equivalent of the dianion 1,3-dilithiopropyne. The latter reacts efficiently with aldehydes and ketones to produce homopropargyl alcohols in a single step route and in high yields.

  在TMEDA存在下，炔丙基溴与两个当量的正丁基锂的受控二锂化反应产生了当量的二价阴离子1,3-二硫代丙炔。后者与醛和酮有效地反应，以一步法并以高收率生产高炔丙醇。
• The Prevalence of Daytime Napping and Its Relationship to Nighttime Sleep
  作者：June J. Pilcher、Kristin R. Michalowski、Renee D. Carrigan

  DOI：10.1080/08964280109595773

  日期：2001.1

  Many healthy adults report daytime napping. Surprisingly few studies, however have examined spontaneous napping behavior especially very short naps, in healthy adults. The authors examined the prevalence of power naps (lasting less than 20 minutes) and longer naps (20 minutes or more) and their effects on nighttime sleep in a group of healthy young and middle-aged adults. The young and middle-aged adults reported very similar sleep and napping patterns, with approximately 74% of the participants in both groups reporting they had napped during a 7-day sleep-log period. Almost half of the participants reported that the average nap lasted less than 20 minutes. A multivariant analysis of variance (MANOVA) found no significant differences between the no-nap and the power-nap or long-nap groups in sleep quantity or quality for either age group. The current data suggested that power napping occurs frequently in healthy adults and that spontaneous napping does not negatively affect nighttime sleep.
• Palladium-Catalyzed One-Pot Conversion of Aldehydes and Ketones into 4-Substituted Homopropargyl Alcohols and 5-En-3-yn-1-ols
  作者：Christian A. Umaña、Jorge A. Cabezas

  DOI：10.1021/acs.joc.7b01529

  日期：2017.9.15

  of 1,3-dilithiopropyne, which adds regiospecifically to aldehydes and ketones to produce homopropargyl alcohols. The lithium acetylide intermediate formed in this protocol can be further reacted with aromatic and vinyl halides, under palladium catalysis, to produce 4-substituted homopropargyl alcohols and 5-en-3-yn-1-ols, respectively, in one-pot with good overall yields.

  用镁和正丁基锂顺序处理2,3-二氯丙烯产生了1,3-二硫代丙炔，这相当于向醛和酮的区域特异性添加，从而生成高炔丙醇。在钯催化下，可以按照此规程形成的乙炔化锂中间体与芳族卤化物和乙烯基卤化物进一步反应，分别在一个锅中以良好的纯度分别生成4-取代的炔丙基醇和5-en-3-yn-1-醇。整体产量。