1-(2-烯丙基苯基)-2-丙烯-1-醇 | 291525-79-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2-烯丙基苯基)-2-丙烯-1-醇
• 中文别名: 4-羟基-3-甲基-2-[(2Z)-戊-2,4-二烯-1-基]环戊-2-烯-1-酮
• 英文名称: 1-(2-allylphenyl)-2-propen-1-ol
• 英文别名: 1-(2-allylphenyl)prop-2-en-1-ol；1-(2-Prop-2-enylphenyl)prop-2-en-1-ol
• CAS: 291525-79-6
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: GCYYUPIYZSUDQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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-(2-烯丙基苯基)-2-丙烯-1-醇 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以45%的产率得到o-Allylphenyl vinyl ketone
  参考文献：
  名称：

  使用不同羰基的铑类胡萝卜素的环化-环加成反应。突出互动的位置

  摘要：

  当用催化量的羧酸铑（II）处理时，发现一系列3-重氮烷二酮可提供通过捕获羰基内酯中间体而衍生的恶双环二极性环加合物。该反应涉及通过将酮类胡萝卜素分子内环化到相邻酮基的氧原子上来产生1，3-偶极。五环和六环羰基烷基化物以相同的效率形成。还对几种α-重氮酮酸酯的串联环化-环加成级联进行了研究，并且级联序列以高收率进行。当相互作用的酮羰基被亚氨基取代时，铑（II）催化的反应进行得不均匀。相反，在用Rh（II）催化剂处理时，α-重氮酰胺基酯不会进行氮挤出。代替，

  DOI：

  10.1021/jo000378f
• 作为产物：
  描述：

  2-甲酰基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 1-(2-烯丙基苯基)-2-丙烯-1-醇
  参考文献：
  名称：

  “Close-to-Release”: Spontaneous Bioorthogonal Uncaging Resulting from Ring-Closing Metathesis

  摘要：

  Bioorthogonal uncaging reactions offer versatile tools in chemical biology. In recent years, reactions have been developed to proceed efficiently under physiological conditions. We present herein an uncaging reaction that results from ring-closing metathesis (RCM). A caged molecule, tethered to a diolefinic substrate, is released via spontaneous 1,4-elimination following RCM. Using this strategy, which we term "close-to-release", we show that drugs and fluorescent probes are uncaged with fast rates, including in the presence of mammalian cells or in the periplasm of Escherichia coli. We envision that this tool may find applications in chemical biology, bioengineering and medicine.

  DOI：

  10.1021/jacs.9b07193

文献信息

• Auto‐Tandem Cooperative Catalysis Using Phosphine/Palladium: Reaction of Morita–Baylis–Hillman Carbonates and Allylic Alcohols
  作者：Peng Chen、Zhi‐Chao Chen、Yue Li、Qin Ouyang、Wei Du、Ying‐Chun Chen

  DOI：10.1002/anie.201814403

  日期：2019.3.18

  here is an unprecedented auto‐tandem cooperative catalysis (ATCC) for Morita–Baylis–Hillman carbonates from isatins and allylic carbonates using a simple Pd(PPh3)4 precursor. Dissociated phosphine generates phosphorus ylides and the Pd leads to π‐allylpalladium complexes, and they undergo a γ‐regioselective allylic–allylic alkylation reaction. Importantly, a cascade intramolecular Heck‐type coupling proceeds

  自动串联催化（ATC）（其中一种催化剂以级联模式促进两个或多个机械上不同的反应）提供了一种从简单的起始原料制备复杂产品的有效策略。此处报道的是使用简单的Pd（PPh 3）4从靛红和烯丙基碳酸酯中对森田-贝利斯-希尔曼碳酸盐进行的史无前例的自动串联协同催化（ATCC ）4前体。离解的磷化氢生成磷酰化物，Pd生成π-烯丙基钯络合物，并且它们进行γ-区域选择性烯丙基-烯丙基烷基化反应。重要的是，进行分子级联的Heck型偶联最终可以提供具有4－亚甲基－2－环戊烯基序的螺硫醇。实验结果表明，Pd和膦都在催化Heck反应中起着至关重要的作用。另外，探索了具有手性膦或手性助剂的不对称形式，并获得了适度的结果。
• Tandem cyclization-cycloaddition reaction of rhodium carbenoids. Studies dealing with intramolecular cycloadditions
  作者：Albert Padwa、Susan F. Hornbuckle、Glen E. Fryxell、Zhijia J. Zhang

  DOI：10.1021/jo00047a032

  日期：1992.10

  A series of 5-alkenyl-1-diazo-2,5-pentanediones, when treated with a catalytic quantity of rhodium(II) acetate, were found to give cycloadducts derived from the intramolecular trapping of a carbonyl ylide intermediate. Tethers of three or four methylenes readily enter into intramolecular cycloaddition, while longer and shorter tethers were reluctant to do so. Alkenes attached to the formally cationic terminus of the carbonyl ylide readily undergo internal cycloaddition if the tether allows for a relatively strain-free transition state. The internal cycloaddition reaction does not occur when the olefinic side chain is attached by means of an ester functionality. Bimolecular trapping experiments established that carbonyl ylide formation occurred, but the dipole does not undergo intramolecular cycloaddition. The inability of these alpha-diazo keto esters to undergo internal cycloaddition is related to conformational factors. The equilibrium between the two possible conformations of the dipole lies predominantly on the side of the Z-isomer. In this orientation, intramolecular dipolar cycloaddition cannot occur, and instead the dipole collapses by means of a proton transfer to give an enol ether.
• <i>Ortho</i>-TMS Benzaldehyde: An Effective Linchpin for Type II Anion Relay Chemistry (ARC)
  作者：Amos B. Smith、Won-Suk Kim、William M. Wuest

  DOI：10.1002/anie.200802301

  日期：2008.9.1

  Ortho-TMS benzaldehyde, an effective bifunctional linchpin for Type II Anion Relay Chemistry (ARC), permits efficient multi-component union of a variety of nucleophiles and electrophiles, including the first example of a Pd-mediated ARC Type II process. To demonstrate the utility of the Type II ARC protocol, a “proof of concept” synthetic sequence was designed and implemented for construction of a focused library of “natural product-like” compounds.
• “Close-to-Release”: Spontaneous Bioorthogonal Uncaging Resulting from Ring-Closing Metathesis
  作者：Valerio Sabatino、Johannes G. Rebelein、Thomas R. Ward

  DOI：10.1021/jacs.9b07193

  日期：2019.10.30

  Bioorthogonal uncaging reactions offer versatile tools in chemical biology. In recent years, reactions have been developed to proceed efficiently under physiological conditions. We present herein an uncaging reaction that results from ring-closing metathesis (RCM). A caged molecule, tethered to a diolefinic substrate, is released via spontaneous 1,4-elimination following RCM. Using this strategy, which we term "close-to-release", we show that drugs and fluorescent probes are uncaged with fast rates, including in the presence of mammalian cells or in the periplasm of Escherichia coli. We envision that this tool may find applications in chemical biology, bioengineering and medicine.
• Cyclization−Cycloaddition Cascade of Rhodium Carbenoids Using Different Carbonyl Groups. Highlighting the Position of Interaction
  作者：Albert Padwa、Zhijia J. Zhang、Lin Zhi

  DOI：10.1021/jo000378f

  日期：2000.8.1

  carboxylate, were found to afford oxabicyclic dipolar cycloadducts derived by the trapping of a carbonyl ylide intermediate. The reaction involves generation of the 1,3-dipole by intramolecular cyclization of the keto carbenoid onto the oxygen atom of the neighboring keto group. Both five- and six-ring carbonyl ylides are formed with the same efficiency. A study of the tandem cyclization-cycloaddition

  当用催化量的羧酸铑（II）处理时，发现一系列3-重氮烷二酮可提供通过捕获羰基内酯中间体而衍生的恶双环二极性环加合物。该反应涉及通过将酮类胡萝卜素分子内环化到相邻酮基的氧原子上来产生1，3-偶极。五环和六环羰基烷基化物以相同的效率形成。还对几种α-重氮酮酸酯的串联环化-环加成级联进行了研究，并且级联序列以高收率进行。当相互作用的酮羰基被亚氨基取代时，铑（II）催化的反应进行得不均匀。相反，在用Rh（II）催化剂处理时，α-重氮酰胺基酯不会进行氮挤出。代替，