2-(phenylseleno)heptanal | 61759-16-8

• 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)heptanal
• 英文别名: Heptanal, 2-(phenylseleno)-；2-phenylselanylheptanal
• CAS: 61759-16-8
• 化学式: C₁₃H₁₈OSe
• 分子量: 269.245
• InChiKey: ZTMSKOFPWAQQEN-UHFFFAOYSA-N

物化性质

• 沸点：
  326.3±34.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  2-(phenylseleno)heptanal 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 methyl (E)-2-[(2-methylpropan-2-yl)oxycarbonylamino]non-3-enoate
  参考文献：
  名称：

  Synthesis of protected racemic β,γ-unsaturated-α-amino acids via γ-phenylseleno-α,β-unsaturated esters

  摘要：

  DOI：

  10.1016/s0040-4039(00)98351-5
• 作为产物：
  描述：

  苯基氯化硒 在 camphor-10-sulfonic acid 作用下， 以 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 23.0h， 生成 2-(phenylseleno)heptanal
  参考文献：
  名称：

  N-Phenylselenosaccharin (NPSSac): a new electrophilic selenium-containing reagent

  摘要：

  A new reagent N-phenylselenosaccharin (NPSSac) was simply prepared and used as a source of the electrophilic phenylselenyl group. This relatively stable new compound was able to react with a series of electron rich organic molecules like alkenes in the presence of external or internal nucleophiles, activated aromatic substrates, or enolizable carbonyl derivatives, under very mild experimental conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.068

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。
• N,N,N-Triphenylselenylisocyanuric Acid (TPSCA): A New Versatile Reagent for α-Phenylselenenylation of Aldehydes and Ketones
  作者：Barahman Movassagh、Ahmad Takallou

  DOI：10.1055/s-0035-1560051

  日期：——

  a source of the electrophilic phenylselenyl group. This relatively stable compound was utilized for an efficient α-selenenylation reaction of aldehydes and ketones catalyzed by l -prolinamide under mild reaction conditions. The organocatalytic asymmetric α-selenenylation of an aldehyde was also studied and the reaction was found to proceed with high enantioselectivity (96% ee).

  已制备、表征并用作亲电子苯基硒基的来源，新的、多功能的试剂 N , N , N - 三苯基硒基异氰脲酸 (TPSCA)。这种相对稳定的化合物用于在温和的反应条件下由 l-脯氨酰胺催化的醛和酮的有效 α-硒基化反应。还研究了醛的有机催化不对称 α-硒基化反应，发现该反应以高对映选择性（96% ee）进行。
• 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。
• 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]
• Unexpectedly easy formation of α-seleno-carbonyl compounds from vinyl selenides
  作者：Alfredo Cravador、Alain Krief

  DOI：10.1039/c39800000951

  日期：——

  Seleno-carbonyl compounds are formed on reaction of seleninic acid or anhydride with vinyl selenides and vinyl sulphides.

  硒代羰基化合物是在硒酸或酸酐与硒化乙烯和硫化乙烯反应后形成的。