2-(phenylseleno)decanal | 68048-50-0

• 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: 2-(phenylseleno)decanal
• 英文别名: 2-Phenylselanyldecanal
• CAS: 68048-50-0
• 化学式: C₁₆H₂₄OSe
• 分子量: 311.326
• InChiKey: ULXDKMGILYVXGP-UHFFFAOYSA-N

物化性质

• 沸点：
  142-143 °C(Press: 0.06 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  癸醛 、 N-(苯硒基)邻苯二甲酰亚胺 在 polystyrene-supported L-proline 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以85%的产率得到2-(phenylseleno)decanal
  参考文献：
  名称：

  聚苯乙烯支持的脯氨酸和脯氨酰胺。用于水中不对称羟醛反应和醛类α-硒烯化反应的通用多相有机催化剂

  摘要：

  已经进行了简单有效的聚苯乙烯负载的脯氨酸和脯氨酰胺的合成。聚苯乙烯负载的脯氨酸已被用作有机溶剂，用于环己酮与取代的苯甲醛在水中的不对称羟醛反应中，而无需任何添加剂。已经观察到高产率，非对映选择性和ee值。该树脂的多功能性在醛的α-硒烯基化中得到证明。脯氨酸和脯氨酰胺树脂均提供了高收率。回收研究表明，脯氨酸树脂的效果比脯氨酰胺树脂好。

  DOI：

  10.1016/j.tetlet.2006.11.040

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。
• One-step Oxidation of Olefins into α-Phenylseleno Carbonyl Compounds
  作者：Makoto Shimizu、Isao Kuwajima

  DOI：10.1246/bcsj.54.3100

  日期：1981.10

  olefins has been examined with the following three types of reagents; (i) (C6H5Se)2–Br2–(Bu3Sn)2O, (ii) (C6H5Se)2–t-BuOOH, and (iii) (C6H6Se)2–(C6H5SeO)2O, and the corresponding α-phenylseleno carbonyl compounds have been obtained directly from the olefins.

  烯烃的氧化已经用以下三种类型的试剂进行了检查；(i) (C6H5Se)2–Br2–(Bu3Sn)2O，(ii) (C6H5Se)2–t-BuOOH，和 (iii) (C6H6Se)2–(C6H5SeO)2O，相应的 α-苯基硒羰基化合物有直接从烯烃中获得。
• A Simple and Efficient <scp>l</scp>-Prolinamide-Catalyzed α-Selenenylation Reaction of Aldehydes
  作者：Wei Wang、Jian Wang、Hao Li

  DOI：10.1021/ol0488946

  日期：2004.8.1

  An efficient and simple l-prolinamide-catalyzed alpha-selenenylation reaction of aldehydes with N-(phenylseleno)phthalimide has been developed for the efficient preparation of alpha-phenylselenoaldehydes. Such compounds are versatile building blocks for the synthesis of alpha,beta-unsaturated aldehydes, allylic alcohols, and amines. [reaction: see text]

  已经开发了醛与N-（苯基硒代）邻苯二甲酰亚胺的有效且简单的1-脯氨酰胺催化的醛的α-硒烯化反应，用于有效制备α-苯基硒代醛。这样的化合物是用于合成α，β-不饱和醛，烯丙基醇和胺的通用结构单元。[反应：看文字]
• Direct, Facile Aldehyde and Ketone α-Selenenylation Reactions Promoted by <scp>l</scp>-Prolinamide and Pyrrolidine Sulfonamide Organocatalysts
  作者：Jian Wang、Hao Li、Yujiang Mei、Bihshow Lou、Dingguo Xu、Daiqian Xie、Hua Guo、Wei Wang

  DOI：10.1021/jo0506940

  日期：2005.7.1

  A new catalytic method for direct alpha-selenenylation reactions of aldehydes and ketones has been developed. The results of exploratory studies have demonstrated that L-prolinamide is an effective catalyst for a-selenenylation reactions of aldehydes, whereas pyrrolidine trifluoromethanesulfonamide efficiently promotes reactions of ketones. Under optimized reaction conditions, using N-(phenylseleno)phthalimide as the selenenylation reagent in CH2Cl2 in the presence of L-prolinamide (2 mol %) or pyrrolidine trifluoromethanesulfonamide (10 mol %), a variety of aldehydes and ketones undergo this process to generate a-selenenylation products in high yields. Mechanistic insight into the L-proline and L-prolinamide catalyzed alpha-selenenylation reactions of aldehydes with N-(phenylseleno)phthalimide has come from theoretical studies employing ab initio methods and density functional theory. The results reveal that (1) the rate-limiting step of the process involves attack of the enamine intermediate at selenium in N-(phenylseleno)phthalimide and (2) the energy of the transition state for the reaction catalyzed by prolinamide is lower than that promoted by proline. This result is consistent with experimental observations. The role of hydrogen bond interactions in stabilizing the transition states for this process is also discussed.
• Oxidation of olefins with diphenyl diselenide-bromine-hexabutyldistannoxane. A one-step preparation of α-phenylseleno carbonyl compounds from olefins
  作者：Isao Kuwajima、Makoto Shimizu

  DOI：10.1016/0040-4039(78)80105-1

  日期：1978.4