(±)-1-(benzyloxy)pent-3-yn-2-ol | 131101-47-8

• 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-(benzyloxy)pent-3-yn-2-ol
• 英文别名: 1-(benzyloxy)-3-pentyn-2-ol；1-Phenylmethoxypent-3-yn-2-ol
• CAS: 131101-47-8
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: IUILTHOPHMETRF-UHFFFAOYSA-N

物化性质

• 沸点：
  327.1±32.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (±)-1-(benzyloxy)pent-3-yn-2-ol 在 sodium hydride 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 silver nitrate 、 calcium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 5.5h， 生成 2-(hydroxymethyl)-3-methyl-5-<(benzyloxy)methyl>furan
  参考文献：
  名称：

  Synthesis of furans by silver(I)-promoted cyclization of allenyl ketones and aldehydes

  摘要：

  A series of conjugated allenones (11b, 12b, 13c; 18a; 18b; 19b, 20b, AB, and 27d) were prepared by [2,3] Wittig rearrangement of (propargyloxy) acetic acids or [(progargyloxy)methy]stannanes followed by oxidation of the resultant allenylcarbinols. These allenones were readily cyclized to 2,3,5-trisubstituted furans upon treatment with AgNO3-CaCO3 in aqueous acetone. Under these conditions 2-(hydroxymethyl)-3,5-dialkylfurans self-condensed to give 2,2'-difurylmethanes.

  DOI：

  10.1021/jo00003a013
• 作为产物：
  描述：

  苄氧基乙醛 、 1-丙炔溴化镁 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (±)-1-(benzyloxy)pent-3-yn-2-ol
  参考文献：
  名称：

  Electrophilic Fluorodesilylation of Allenylmethylsilanes:  A Novel Entry to 2-Fluoro-1,3-dienes

  摘要：

  Various fluorodienes were prepared by treatment of the corresponding allenylmethylsilanes with Selectfluor. This is the first route to these compounds not based on the use of a fluorinated building block. The reaction allows the preparation of 2-fluoro-1,3-dienes with several substitution patterns, including di- and trisubstituted compounds.

  DOI：

  10.1021/ol047319z

文献信息

• Synthesis of Alkylidene(<i>gem</i>-Difluorocyclopropanes) from Propargyl Glycolates by a One-Pot Difluorocyclopropenation/Ireland–Claisen Rearrangement Sequence
  作者：Guillaume Ernouf、Jean-Louis Brayer、Benoît Folléas、Jean-Pierre Demoute、Christophe Meyer、Janine Cossy

  DOI：10.1021/acs.joc.7b00197

  日期：2017.4.7

  difluorocyclopropenation/Ireland–Claisen rearrangement sequence applied to readily available propargyl glycolates was developed as a route toward functionalized alkylidene(gem-difluorocyclopropanes). This strategy conveniently avoids the isolation of the unstable 3,3-difluorocyclopropenylcarbinyl glycolates arising from the difluorocyclopropenation. The Ireland–Claisen rearrangement proceeds with high

  一锅法二氟环丙烷/爱尔兰-克莱森重排序列适用于现成的炔丙基乙醇酸酯，是开发向官能化亚烷基（gem -difluorocyclopropanes）的一种途径。该策略方便地避免了由二氟环丙烷化引起的不稳定的3，3-二氟环丙烯基羰基羰基乙醇酸酯的分离。爱尔兰-克莱森重排过程以高非对映选择性和手性转移进行，得到亚烷基（宝石-二氟环丙烷），并带有季立体中心和受保护的乙醇酸部分，这对于制备官能化的宝石-二氟环丙烷是有用的基础。
• Inhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; a novel potent inhibitor of AI-2 signalling
  作者：Manikandan Kadirvel、Fariba Fanimarvasti、Sarah Forbes、Andrew McBain、John M. Gardiner、Gavin D. Brown、Sally Freeman

  DOI：10.1039/c3cc49678c

  日期：——

  (±)4-Fluoro-DPD completely inhibited bioluminescence and bacterial growth of Vibrio harveyi BB170 strain by disruption of quorum sensing cascade.

  (±)4-氟-DPD通过破坏群体感应级联完全抑制了Vibrio harveyi BB170菌株的发光和细菌生长。
• JPS6396145A
  申请人：——

  公开号：JPS6396145A

  公开（公告）日：1988-04-27
• Electrophilic Fluorodesilylation of Allenylmethylsilanes:  A Novel Entry to 2-Fluoro-1,3-dienes
  作者：M Carmen Pacheco、Véronique Gouverneur

  DOI：10.1021/ol047319z

  日期：2005.3.1

  Various fluorodienes were prepared by treatment of the corresponding allenylmethylsilanes with Selectfluor. This is the first route to these compounds not based on the use of a fluorinated building block. The reaction allows the preparation of 2-fluoro-1,3-dienes with several substitution patterns, including di- and trisubstituted compounds.
• Synthesis of furans by silver(I)-promoted cyclization of allenyl ketones and aldehydes
  作者：James A. Marshall、Xiao Jun Wang

  DOI：10.1021/jo00003a013

  日期：1991.2

  A series of conjugated allenones (11b, 12b, 13c; 18a; 18b; 19b, 20b, AB, and 27d) were prepared by [2,3] Wittig rearrangement of (propargyloxy) acetic acids or [(progargyloxy)methy]stannanes followed by oxidation of the resultant allenylcarbinols. These allenones were readily cyclized to 2,3,5-trisubstituted furans upon treatment with AgNO3-CaCO3 in aqueous acetone. Under these conditions 2-(hydroxymethyl)-3,5-dialkylfurans self-condensed to give 2,2'-difurylmethanes.