1-(phenylselanyl)propan-2-one | 61759-13-5

• 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-(phenylselanyl)propan-2-one
• 英文别名: 2-Propanone, 1-(phenylseleno)-；1-phenylselanylpropan-2-one
• CAS: 61759-13-5
• 化学式: C₉H₁₀OSe
• 分子量: 213.138
• InChiKey: JSSLATKTLCWQNP-UHFFFAOYSA-N

物化性质

• 沸点：
  72-74 °C(Press: 0.1 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(phenylselanyl)propan-2-one 在 tin(ll) chloride 水 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-methyl-3-prop-2-enyl phenylselenide
  参考文献：
  名称：

  Transformation of α-phenylseleneketones to allylic selenides via migration of the phenylseleno group

  摘要：

  DOI：

  10.1016/s0040-4039(00)88359-8
• 作为产物：
  描述：

  1-[dichloro(phenyl)-λ4-selanyl]propan-2-one 在 硫脲 作用下， 以 丙酮 为溶剂， 以99%的产率得到1-(phenylselanyl)propan-2-one
  参考文献：
  名称：

  苯基三氯化硒的合成。与酮反应。亚硒酸盐消除反应的新变化

  摘要：

  使用苯基三氯化硒将PhSeCl 2-基团引入酮的α-位。这些产物被转化为烯酮（水解/亚硒酸酯消除）或α-苯基硒酮（硫脲还原）。

  DOI：

  10.1016/s0040-4039(01)84605-0

文献信息

• Synthesis of Selenium-Substituted Pyrroles and Pyrazol-3-ones
  作者：Orazio Attanasi、Lucia De Crescentini、Marcello Tiecco、Fabio Mantellini、Francesca Marini、Simona Nicolini、Silvia Sternativo

  DOI：10.1055/s-0029-1216630

  日期：2009.4

  An approach to the synthesis of 4-(phenylseleno)pyrroles, 4-(phenylseleno)pyrazol-3-ones, and 4-(1,3-benzoselenazol-2-ylthio)pyrazol-3-ones is described. Their formation passes through hydrazonic intermediates obtained by the reaction between 1,2-diaza-1,3-butadienes and l-(phenylseleno)ketones, phenylselenol, or 2-mercaptobenzoselenazole, respectively.

  描述了一种合成 4-(phenylseleno)pyrroles、4-(phenylseleno)pyrazol-3-ones 和 4-(1,3-benzoselenazol-2-ylthio)pyrazol-3-ones 的方法。它们的形成分别通过 1,2-二氮杂-1,3-丁二烯和 l-（苯基硒基）酮、苯基硒醇或 2-巯基苯并硒唑之间的反应获得的腙中间体。
• Use of Phenylselenium Trichloride For Simple and Rapid Preparation of α-Phenylselanyl Aldehydes and Ketones
  作者：Didier Houllemare、Sylvain Ponthieux、Francis Outurquin、Claude Paulmier

  DOI：10.1055/s-1997-1509

  日期：1997.1

  α-Phenylselanyl aldehydes are prepared on a large scale by reaction of PhSeCl3 with the corresponding aldehydes in acetonitrile without isolation of the intermediate dichloro adducts. This method has been applied to α-phenylselanyl ketones derived from alkyl aryl ketones, symmetrical aliphatic ketones and alkyl isopropyl ketones. cis-4-tert-Butyl-2-phenylselanylcyclohexanone was also prepared in the same way.

  α-苯硒基醛通过PhSeCl3与相应醛在乙腈中反应大规模制备，无需分离二氯加成中间体。该方法已应用于由烷基芳基酮、对称脂肪酮和烷基异丙基酮衍生的α-苯硒基酮，并同样制备了顺-4-叔丁基-2-苯硒基环己酮。
• A convenient method for the synthesis of α-phenylselenenyl carbonyl compounds
  作者：Noritaka Miyoshi、Tetsuya Yamamoto、Nobuaki Kambe、Shinji Murai、Noboru Sonoda

  DOI：10.1016/s0040-4039(00)85720-2

  日期：1982.1

  Treatment of ketones or aldehydes with selenium dioxide and diphenyl diselenide in the presence of acid catalyst afforded the corresponding α-phenylselenenyl carbonyl compounds in good yields.

  在酸催化剂的存在下用二氧化硒和二苯二硒化物处理酮或醛，以良好的收率得到相应的α-苯基硒烯基羰基化合物。
• Evidence for a common selenolate intermediate in the glutathione peroxidase-like catalysis of α-(phenylselenenyl) ketones and diphenyl diselenide
  作者：Lars Engman、Claes Andersson、Ralf Morgenstern、Ian A. Cotgreave、Carl-Magnus Andersson、Anders Hallberg

  DOI：10.1016/s0040-4020(01)87004-6

  日期：1994.2

  glutathione peroxidase-like catalysis of α-(phenylselenenyl) ketones was investigated. Degradation studies demonstrated the rapid cleavage of the aliphatic carbon-selenium bond of α-(phenylselenenyl) ketones by glutathione at pH 6.9 in a methanolic phosphate buffer under argon. On treatment with excess glutathione under aerobic conditions, α-(phenylselenenyl) ketones, S-(phenylselenenyl)glutathione and

  研究了谷胱甘肽过氧化物酶样α-（苯基硒烯基）酮的催化作用。降解研究表明，在氩气下，在pH值为6.9的甲醇磷酸盐缓冲液中，谷胱甘肽可快速裂解α-（苯基硒烯基）酮的脂肪族碳-硒键。在有氧条件下用过量的谷胱甘肽处理后，α-（苯基硒烯基）谷胱甘肽和S-（苯基硒烯基）谷胱甘肽和二苯基二硒化物都显示出苯硒酸酯。发现该材料被过氧化氢的氧化比α-（苯基硒烯基）酮，S-（苯基硒烯基）谷胱甘肽或二苯基二硒化物快得多。涉及苯硒酸酯的催化机理，
• [EN] ORGANOCATALYSTS AND METHODS OF USE IN CHEMICAL SYNTHESIS<br/>[FR] ORGANOCATALYSEURS ET PROCEDES D'UTILISATION DE CES DERNIERS DANS LA SYNTHESE CHIMIQUE
  申请人：STC UNM

  公开号：WO2006007586A1

  公开（公告）日：2006-01-19

  The present invention pertains generally to compositions comprising organocatalysts that facilitate stereo-selective reactions and the method of their synthesis and use. Particularly, the invention relates to metal-free organocatalysts for facilitation of stereo-­selective reactions, and the method of their synthesis and use. These compounds have the structure of the Formulas (I) and (II). Where X is independently selected from CH2, N-Ra, O, S or C=O; Y is CH2, N-Ra, O, S or C=O, with the proviso that at least one of X or Y is CH2, and preferably both of X and Y are CH2; Ra is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6 alkyl including a C3-C6 cyclic alkyl group, or an optionally substituted aryl group, preferably an optionally substituted phenyl group; Rb is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6 acyclic or a a C3-C6 cyclic alkyl group, CHO, N(Me)O, CO(S)Ra or the group of Formula (III). Where Rc and Rd are each independently H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C12 alkyl, more preferably a C1-C6 alkyl, and an optionally substituted aryl group, or together Rc and Rd form an optionally substituted carbocyclic or optionally substituted heterocyclic ring; R1 is OH, OR, NR'R', NHC(=O)R, NHSO2R; R2 is H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1­C6 alkyl, an optionally substituted aryl group or a =O group (which establishes a carbonyl group with the carbon to which =O is attached; R3 is H, OH, F, C1, Br, I, Cl, an optionally substituted C1-C20 alkyl, alkenyl or alkynyl ('hydrocarbyl') group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl, such that the carbon to which R3 is attached has an R or S configuration; R is H, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group, R' and R' are each independently H, an optionally substituted C1-C20 alkyl group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group; or together R' and R' form an optionally substituted heterocyclic, preferably a 4 to 7 membered optionally substituted heterocyclic group or an optionally substituted heteroaryl ring with the nitrogen to which R' and R' are attached; and wherein said compound is free from a metal catalyst.

  本发明涉及一般包括有机催化剂的组合物，该催化剂促进立体选择性反应以及其合成和使用方法。特别地，本发明涉及无金属有机催化剂以促进立体选择性反应，以及其合成和使用方法。这些化合物具有以下结构的式（I）和（II）。其中X独立地选择自CH2、N-Ra、O、S或C=O；Y为CH2、N-Ra、O、S或C=O，但至少X或Y中的一个为CH2，最好是X和Y都为CH2；Ra为H、可选择地取代的C1-C12烷基，最好是可选择地取代的C1-C6烷基，包括C3-C6环烷基，或可选择地取代的芳基，最好是可选择地取代的苯基；Rb为H、可选择地取代的C1-C12烷基，最好是可选择地取代的C1-C6无环或C3-C6环烷基，CHO、N(Me)O、CO(S)Ra或式（III）的基团。其中Rc和Rd各自独立地为H、F、C1、可选择地取代的C1-C20烷基，最好是可选择地取代的C1-C12烷基，更好地是C1-C6烷基，以及可选择地取代的芳基，或者Rc和Rd一起形成可选择地取代的碳环或可选择地取代的杂环；R1为OH、OR、NR'R'、NHC(=O)R、NHSO2R；R2为H、F、C1、可选择地取代的C1-C20烷基，最好是可选择地取代的C1-C6烷基，可选择地取代的芳基或=O基团（与=O连接的碳形成羰基基团）；R3为H、OH、F、C1、Br、I、Cl、可选择地取代的C1-C20烷基、烯基或炔基（'烃基'），最好是可选择地取代的C1-C6烷基，或可选择地取代的芳基，使得R3连接的碳具有R或S构型；R为H、可选择地取代的C1-C20烷基，最好是可选择地取代的C1-C6烷基，或可选择地取代的芳基，R'和R'各自独立地为H、可选择地取代的C1-C20烷基，最好是可选择地取代的C1-C6烷基，或可选择地取代的芳基；或者R'和R'一起形成可选择地取代的杂环，最好是4到7成员的可选择地取代的杂环基团或与R'和R'连接的氮原子形成可选择地取代的杂芳基环；其中所述化合物不含金属催化剂。

表征谱图