<α-2H>acrylophenone | 147991-75-1

• 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: <α-2H>acrylophenone
• 英文别名: [α-2H]acrylophenone；2-deuterio-1-phenylprop-2-en-1-one
• CAS: 147991-75-1
• 化学式: C₉H₈O
• 分子量: 133.154
• InChiKey: KUIZKZHDMPERHR-VMNATFBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  10.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  <α-2H>acrylophenone 、 aluminum isopropoxide 生成 1-phenyl<2-2H1>prop-2-en-1-ol
  参考文献：
  名称：

  DENHEZ J.-P.; GIRAULT G.; DIZABO P., J. LABELLED COMPOUNDS AND RADIOPHARM., 1981, 18, NO 5, 759-763

  摘要：

  DOI：
• 作为产物：
  描述：

  α,α-dideutero-β-chloropropiophenone 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 <α-2H>acrylophenone
  参考文献：
  名称：

  Popov, A. F.; Matvienko, V. N.; Piskunova, Zh. P., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 10, p. 1922 - 1924

  摘要：

  DOI：

文献信息

• Ruthenium-Catalyzed Functionalization of Pyrroles and Indoles with Propargyl Alcohols
  作者：Nora Thies、Cristian G. Hrib、Edgar Haak

  DOI：10.1002/chem.201200188

  日期：2012.5.14

  Several ruthenium‐catalyzed atom‐economic transformations of propargyl alcohols with pyrroles or indoles leading to alkylated, propargylated, or annulated heteroaromatics are reported. The mechanistically distinct reactions are catalyzed by a single ruthenium(0) complex containing a redox‐coupled dienone ligand. The mode of activation regarding the propargyl alcohols determines the reaction pathway

  据报道，几种钌催化的炔丙醇与吡咯或吲哚的原子经济转化会导致烷基化，炔丙基化或环化的杂芳族化合物。在机理上截然不同的反应是由包含氧化还原偶联的二烯酮配体的单一钌（0）配合物催化的。关于炔丙醇的活化方式决定了反应途径，并取决于醇的取代方式。次级底物通过1,2-氢转移形成烯基配合物，而第三级底物的转化涉及亚烯基中间体。1-乙烯基炔丙醇通过级联烯丙基化/环化序列转化。
• A Cooperative Catalysis Approach to the Morita-Baylis-Hillman Reaction of Aryl Vinyl Ketones
  作者：Kyungsoo Oh、Jian-Yuan Li

  DOI：10.1055/s-0030-1260468

  日期：2011.6

  achieved for the first time through cooperative catalysis of proline and brucine N-oxide. A unique mode of activation of the aldehydes through proline iminium intermediates has been identified as a key reaction parameter for the successful MBH reaction of aryl vinyl ketones. The reaction pathways leading to 1:2 MBH products under typical nucleophilic catalysis conditions were investigated. A systematic

  芳基乙烯基酮的Morita-Baylis-Hillman（MBH）反应是首次通过脯氨酸和Brucine N-氧化物的协同催化而实现的。通过脯氨酸亚胺鎓中间体活化醛的独特方式已被确定为芳基乙烯基酮成功进行MBH反应的关键反应参数。研究了在典型的亲核催化条件下导致1：2 MBH产物的反应途径。一项系统的研究揭示了导致MBH产物为1：2的两种不同反应途径：（1）正常MBH产物与芳基乙烯基酮的第二反应是反应初期的主要反应途径，以及（2）羟醛反应Rauhut-Currier产品与醛的合成途径 （酒精产物的自催化作用）是反应后期的主要反应途径。 醛醇缩合反应-生物碱-催化-酮-亲核试剂
• Dimmock; Shyam; Smith, Pharmazie, 1984, vol. 39, # 7, p. 467 - 470
  作者：Dimmock、Shyam、Smith

  DOI：——

  日期：——
• Popov, A. F.; Matvienko, V. N.; Piskunova, Zh. P., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 7, p. 1158 - 1161
  作者：Popov, A. F.、Matvienko, V. N.、Piskunova, Zh. P.

  DOI：——

  日期：——
• Stereoselective ring opening of 1-phenylcyclopropylamine catalyzed by monoamine oxidase-B
  作者：Richard B. Silverman、Joseph M. Cesarone、Xingliang Lu

  DOI：10.1021/ja00065a002

  日期：1993.6

  The inactivation of monoamine oxidase (MAO) by 1-phenylcyclopropylamine (1-PCPA, 1) has been proposed (Silverman, R. B.; Zieske, P. A. Biochemistry 1985,24,2128-2138) to proceed via a radical mechanism involving ring opening of an unstable cyclopropylaminyl radical (Scheme I). This intermediate has been shown to partition between attachment to the N-5 position of the covalently-bound flavin cofactor, which results in irreversible inactivation, and attachment to an active-site cysteine residue, which results in an unstable adduct that hydrolyzes to release acrylophenone and active enzyme over time. The stereochemistry and mechanism of the ring-opening step is investigated in this paper. The enantiomerically pure dideuterated 1-PCPA analogues 5 and 6 were prepared and used to inactivate MAO. Extractions of the acrylophenone metabolites released on decomposition of the reversible cysteine adducts that were formed during inactivation by 5 and by 6 were subjected to GCMS analysis. It was found that the inactivation by the R-isomer (5) produced 66% of [beta,beta-H-2(2)]acrylophenone, 19% of [alpha-H-2]acrylophenone, and 15% of unlabeled acrylophenone; inactivation by the S-isomer (6) resulted in formation of 4% of [beta,beta-H-2(2)]acrylophenone, 6% of [alpha-H-2]-acrylophenone, and 90% of unlabeled acrylophenone. These results are indicative of a stereoselective ring opening, preferentially forming beta,beta-dideutero adduct 8 following inactivation by 5 (Scheme II) and the alpha,alpha-dideuterio adduct 13 following inactivation by 6 (Scheme III). Stereoselective exchange of a single a deuterium on adduct 13 is proposed to account for the complete washout of deuterium in the product and the observed deuterium isotope effect of 3.1 on the reactivation of 6-inactivated MAO. The difference in the amount of cleavage of the two cyclopropyl bonds with each enantiomer may be due, at least in part, to a secondary deuterium isotope effect on the formation of the dideuterated carbon radical. This secondary deuterium isotope effect also provides a rationalization that favors a mechanism involving electron transfer to the aminium radical cation followed by cyclopropyl ring cleavage and then combination with an active-site cysteine radical. The results do not support a direct S(H)2 mechanism. The preference for cleavage of one of the cyclopropane bonds is believed to be the result of asymmetry at the active site which is set up for stereospecific removal of the pro-R proton from substrates; the pro-R C-H bond of substrates corresponds to the cyclopropane bond in 1-PCPA that is preferentially broken.