α-phenylselenenyl propionaldehyde | 84782-51-4

• 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-phenylselenenyl propionaldehyde
• 英文别名: α-phenylselenyl propionaldehyde；(+/-)-2-phenylselenopropionaldehyde；(+/-)-2-(phenylseleno)propanal；α-phenylselenopropanal；methyl-phenylseleno-ethanal；2-(phenylseleno)propanal；Propanal, 2-(phenylseleno)-；2-phenylselanylpropanal
• CAS: 84782-51-4
• 化学式: C₉H₁₀OSe
• 分子量: 213.138
• InChiKey: XNCJRVWXDRHXFM-UHFFFAOYSA-N

物化性质

• 沸点：
  84 °C(Press: 0.2 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：

  α-phenylselenenyl propionaldehyde 以85%的产率得到
  参考文献：
  名称：

  NISHIYAMA, HISAO;KITAJIMA, TOSHIO;YAMAMOTO, AKIKO;ITOH, KENJI, J. CHEM. SOC. CHEM. COMMUN., 1982, N 21, 1232-1233

  摘要：

  DOI：
• 作为产物：
  描述：

  phenylselenium trichloride 在 水 、 硫脲 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 α-phenylselenenyl propionaldehyde
  参考文献：
  名称：

  Use of Phenylselenium Trichloride For Simple and Rapid Preparation of α-Phenylselanyl Aldehydes and Ketones

  摘要：

  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。

  DOI：

  10.1055/s-1997-1509

文献信息

• [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。
• 含苯硒基的喹喔啉类化合物及其制备与应用
  申请人：浙江工业大学

  公开号：CN104016931B

  公开（公告）日：2016-06-15

  本发明公开了一种含苯硒基的喹喔啉类化合物及其制备和应用，所述含苯硒基的喹喔啉类化合物的结构如式(V)所示，其合成路线如下反应方程式所示。本发明提供的含苯硒基的喹喔啉类化合物具有良好的单胺氧化酶抑制活性，可用于制备单胺氧化酶抑制剂。
• K₂S₂O₈-promoted C–Se bond formation to construct α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds
  作者：Xue-Yan Yang、Ruizhe Wang、Lu Wang、Jianjun Li、Shuai Mao、San-Qi Zhang、Nanzheng Chen

  DOI：10.1039/d0ra05927g

  日期：——

  oxidant in the absence of catalyst and afford desired products in moderate to excellent yields. This protocol provides a very simple route for the synthesis of α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds.

  已经开发了一种新的 K 2 S 2 O 8促进中性条件下交叉偶联形成的 C-Se 键。在没有催化剂的情况下，使用 K 2 S 2 O 8作为氧化剂，多种醛和酮反应良好，并以中等至优异的产率提供所需的产物。该协议为合成α-苯基硒羰基化合物和α、β-不饱和羰基化合物提供了一条非常简单的路线。
• New rearrangement of phenylseleno- and trimethylsilylmethyl groups in 2-hydroxy-3-trimethylsilylpropyl selenides
  作者：Hisao Nishiyama、Toshio Kitajima、Akiko Yamamoto、Kenji Itoh

  DOI：10.1039/c39820001232

  日期：——

  2-Hydroxy-3-trimethylsilyl-propyl selenides, readily prepared by the reaction of α-phenylselenoaldehydes and trimethylsilylmethyl-lithium, are transformed into primary allylic selenides and β-trimethylsilylpropanals by acid-catalysed dehydroxysilylation accompanied by a phenylseleno-shift, and by silver-induced rearrangement of the trimethylsilylmethyl group, respectively.

  易于通过α-苯基硒醛与三甲基硅烷基甲基锂反应制得的2-羟基-3-三甲基甲硅烷基丙基硒化物，通过酸催化的脱羟基甲硅烷基化并伴有苯基硒基转移，并通过银转化为伯烯丙基硒化物和β-三甲基甲硅烷基丙醛。诱导的三甲基甲硅烷基甲基的重排。
• Preparation of silyl enol ethers derived from α-phenylseleno aldehydes and α-phenylseleno ketones
  作者：Sylvain Ponthieux、Francis Outurquin、Claude Paulmier

  DOI：10.1016/0040-4020(95)00532-d

  日期：1995.8

  experimental conditions for the preparation of trimethylsilyl enol ethers 3 from α-phenylseleno aldehydes 1, compatible with a limited deselenenylation of the substrate, were studied. Starling from α-phenylseleno ketones 2, the enoxysilanes 4, bearing a vinylic PhSe group, are the major products when triethylamine is the base. Trimethylsilyl enol ethers 5 with an allylic PhSe group arc also formed beside 4

  研究了由α-苯基硒基醛1制备三甲基甲硅烷基烯醇醚3的最佳实验条件，该底物与底物的有限的硒烯基化作用相容。当以三乙胺为碱时，带有乙烯基PhSe基团的环氧硅烷4是由α-苯基硒基酮2形成的星形化合物。当在较低温度下使用LDA或KH时，在4旁边还会形成具有烯丙基PhSe基团的三甲基甲硅烷基烯醇醚5。