ethyl 6-oxohex-2-enoate | 26392-27-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 6-oxohex-2-enoate
• CAS: 26392-27-8
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: AERNDGQPWSLYDI-UHFFFAOYSA-N

物化性质

• 沸点：
  231.8±23.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6-oxohex-2-enoate 在 羟胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 ((2S,5R)-1-Hydroxy-5-{2-[(E)-hydroxyimino]-propyl}-pyrrolidin-2-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Facile synthesis of α,α′ disubstituted N-hydroxypyrrolidines and N-hydroxypiperidines via double 1,4-addition of hydroxylamine

  摘要：

  A versatile synthesis of alpha and alpha' disubstituted N-hydroxypiperidine and N-hydroxypyrrolidine by consecutive double 1,4-addition of hydroxylamine on the corresponding bis alpha,beta-tinsaturated diester is described. This reaction takes place an environmentally friendly (ethanol/water) system and at room temperature. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.064
• 作为产物：
  描述：

  (E)-6,6-Diethoxy-hex-2-enoic acid ethyl ester 在 磷酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 ethyl 6-oxohex-2-enoate
  参考文献：
  名称：

  Kovalev,B.G. et al., Journal of Organic Chemistry USSR (English Translation), 1969, vol. 5, p. 1718 - 1721

  摘要：

  DOI：

文献信息

• Desymmetrization of diols by a tandem oxidation/Wittig olefination reaction
  作者：David J. Phillips、Kathryn S. Pillinger、Wei Li、Angela E. Taylor、Andrew E. Graham

  DOI：10.1039/b602329k

  日期：——

  Diols are desymmetrized by a tandem oxidation/Wittig olefination to give alpha,beta-unsaturated hydroxy esters without the requirement for protecting group strategies; the alpha,beta-unsaturated hydroxy esters are transformed into dienyl diesters using a second oxidation/Wittig olefination sequence using PCC.

  通过串联氧化/维蒂希（Wittig）烯化反应使二元醇脱对称，得到α，β-不饱和羟基酯，而无需保护基团的策略；使用PCC，通过第二次氧化/维蒂希烯化序列将α，β-不饱和羟基酯转化为二烯基二酯。
• Guanidine Bases in Synthesis: Extending the Scope of the Corey-Chaykovsky Epoxidation
  作者：Andrew Graham、David Phillips

  DOI：10.1055/s-0029-1219359

  日期：2010.3

  Guanidine bases, such as 1,5,7-triazabicyclo[4.4.0]dec-1-ene (TBD) or 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-1-ene (MTBD), are highly effective reagents for the in situ generation of sulfonium ylides from sulfonium salts in Corey-Chaykovsky epoxidation reactions of aldehydes. These reactions proceed rapidly to produce the corresponding epoxides in excellent yields and with high selectivity for the trans product. Significantly, this reagent combination is applicable to both nonenolizable and enolizable aldehydes and α,β-unsaturated aldehydes.

  胍基化合物，如1,5,7-三氮杂双环[4.4.0]癸-1-烯（TBD）或7-甲基-1,5,7-三氮杂双环[4.4.0]癸-1-烯（MTBD），是有效的试剂，可在Corey-Chaykovsky环氧化反应中可以原位生成磺壳盐中的磺烯烃。这些反应迅速进行，生成相应的环氧化物，产率极高，并且对反式产物具有较高的选择性。值得注意的是，这种试剂组合适用于不可酯化和可酯化的醛以及α,β-不饱和醛。
• A General Catalyst for Site-Selective C(sp³)–H Bond Amination of Activated Secondary over Tertiary Alkyl C(sp³)–H Bonds
  作者：Ryan J. Scamp、James G. Jirak、Nicholas S. Dolan、Ilia A. Guzei、Jennifer M. Schomaker

  DOI：10.1021/acs.orglett.6b01392

  日期：2016.6.17

  catalyst-controlled and selective carbon–hydrogen (C–H) bond amination of activated secondary C–H bonds over tertiary alkyl C(sp3)–H bonds is challenging, as substrate control often dominates when reactive nitrene intermediates are involved. In this letter, we report the design of a new silver complex, [(Py5Me2)AgOTf]2, that displays general and good-to-excellent selectivity for nitrene insertion into

  作为底物控制，发现能够促进活化的二级 C-H 键在叔烷基 C(sp 3 )-H 键上的一般、催化剂控制和选择性碳-氢 (C-H) 键胺化的过渡金属配合物的发现具有挑战性当涉及反应性氮烯中间体时，通常占主导地位。在这封信中，我们报告了一种新的银配合物 [(Py 5 Me 2 )AgOTf] 2的设计，该配合物在将氮烯插入炔丙基、苄基和烯丙基 C-H 键时表现出普遍和良好的选择性。叔烷基 C(sp 3 )-H 键。
• Unsaturated aromatic amides as pesticides
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0111105A2

  公开（公告）日：1984-06-20

  The specification describes and claims methods of controlling acarine pests by application of a compound of Formula (I), methods of controlling arthropod pests by application of a compound of Formula (IA), compounds of Formula (IA) per se, pesticidal compositions comprising a compound of Formula (IA), and processes for preparing a compound of Formula (IA).

  本说明书描述并权利要求通过施用式（I）化合物控制螨类害虫的方法、通过施用式（IA）化合物控制节肢动物害虫的方法、式（IA）化合物本身、包含式（IA）化合物的杀虫组合物以及制备式（IA）化合物的工艺。
• Sequential- and tandem-oxidation–epoxidation reactions employing guanidine bases
  作者：David J. Phillips、Joseline L. Kean、Andrew E. Graham

  DOI：10.1016/j.tet.2013.05.036

  日期：2013.7

  1,5,7-Triazabicyclo[4.4.0]dec-1-ene (TBD) and 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-1-ene (MTBD) promote the efficient formation of sulfonium ylides from sulfonium salts in the Corey-Chaykovsky epoxidation of aldehydes and provide excellent yields of the corresponding epoxides. This reaction protocol can be further adapted to allow for the development of both sequential and tandem-oxidation-epoxidation protocols from aldehydes generated in situ by manganese dioxide (MnO2) or barium manganate (BaMnO4) mediated oxidation reactions. (C) 2013 Elsevier Ltd. All rights reserved.