(E)-ethyl 3-methylnon-2-enoate | 22268-09-3

• 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: (E)-ethyl 3-methylnon-2-enoate
• 英文别名: ethyl (E)-3-methylnon-2-enoate；ethyl (2E)-3-methylnon-2-enoate
• CAS: 22268-09-3
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: KTRQMKFGPLUMQQ-ZHACJKMWSA-N

物化性质

• 沸点：
  254.1±9.0 °C(Predicted)
• 密度：
  0.887±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-methylnon-2-enoate 在 platinum(IV) oxide lithium aluminium tetrahydride 、 氢气 、 三溴化磷 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 5-Methyl-undecansaeure
  参考文献：
  名称：

  Structure and Reactivity. I. The Oximation Rates of Some Straight-Chain and Monomethyl-Substituted Alkanones

  摘要：

  DOI：

  10.1021/jo01029a022
• 作为产物：
  描述：

  3-羟基-3-甲基壬酸乙酯 在 phosphorus pentoxide 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 (E)-ethyl 3-methylnon-2-enoate
  参考文献：
  名称：

  Structure and Reactivity. I. The Oximation Rates of Some Straight-Chain and Monomethyl-Substituted Alkanones

  摘要：

  DOI：

  10.1021/jo01029a022

文献信息

• Highly E-selective solvent-free Horner–Wadsworth–Emmons reaction catalyzed by DBU
  作者：Kaori Ando、Kyohei Yamada

  DOI：10.1039/c1gc15134g

  日期：——

  The solvent-free Horner–Wadsworth–Emmons reaction of triethyl phosphonoacetate with a variety of aldehydes was catalyzed by DBU in the presence of K2CO3 to give E-α,β-unsaturated esters highly selectively (99:1 for most of the reactions). The reaction with ketones gave trisubstituted olefins with good to high E-selectivity by DBU-Cs2CO3.

  这 溶剂无Horner–Wadsworth–Emmons的反应 膦酸三乙酯 与各种 醛类DBU在K 2 CO 3的存在下催化得到E -α，β-不饱和酯类高度选择性（大多数反应为99 ：1）。与之反应酮类 给出三取代 烯烃DBU-Cs 2 CO 3具有良好的电子选择性，甚至具有很高的电子选择性。
• Chromium(II)-Catalyzed Diastereoselective and Chemoselective Csp²–Csp³ Cross-Couplings Using Organomagnesium Reagents
  作者：Jie Li、Qianyi Ren、Xinyi Cheng、Konstantin Karaghiosoff、Paul Knochel

  DOI：10.1021/jacs.9b08586

  日期：2019.11.13

  A simple protocol for performing chromium-catalyzed highly diastereoselective alkylations of arylmagnesium halides with cyclohexyl iodides at ambient temperature has been developed. Furthermore, this ligand-free CrCl2 enables efficient electrophilic alkenylations of primary, secondary and tetiary alkylmagnesium halides with readily available alkenyl acetates. Moreover, this chemoselective C‒C coupling

  已开发出一种在环境温度下用环己基碘对芳基镁卤化物进行铬催化的高度非对映选择性烷基化的简单方案。此外，这种不含配体的 CrCl2 能够使伯、仲和叔烷基卤化镁与容易获得的乙酸烯基酯进行有效的亲电烯基化。此外，这种与立体定义的烯基乙酸酯的化学选择性 C-C 偶联反应以立体保留方式进行。烷基碘化物和烯基乙酸酯上的各种官能团具有良好的耐受性，从而以良好的收率和高非对映选择性提供官能化的 Csp2-Csp3 偶联产物。详细的机理研究表明，原位生成的低价铬 (I) 物种可能是这些 Csp2-Csp3 交叉偶联的活性催化剂。
• SUBSTITUTED CYANO CYCLOALKYL PENTA-2,4-DIENES, CYANO CYCLOALKYL PENT-2-EN-4-YNES, CYANO HETEROCYCLYL PENTA-2,4-DIENES AND CYANO HETEROCYCLYL PENT-2-EN-4-YNES AS ACTIVE SUBSTANCES
  申请人：BAYER CROPSCIENCE AKTIENGESELLSCHAFT

  公开号：US20170210701A1

  公开（公告）日：2017-07-27

  The invention relates to cyano cycloalkyl penta-2,4-dienes, cyano cycloalkyl pent-2-en-4-ynes, cyano heterocyclyl penta-2,4-dienes and cyano heterocyclyl pent-2-en-4-ynes of general formula (I), or the salts thereof, where [X-Y], Q, R 1 , R 2 , A 1 , A 2 , V, W, m and n have the definitions specified in the description. The invention also relates to a production method for same and to the use of same for increasing stress tolerance in plants against abiotic stress, and/or for increasing the plant yield.

  该发明涉及一般式(I)的氰基环烷基戊二烯、氰基环烷基戊-2-炔、氰基杂环烷基戊二烯和氰基杂环烷基戊-2-炔，或其盐，其中[X-Y]、Q、R1、R2、A1、A2、V、W、m和n的定义如描述中所指定。该发明还涉及同类物质的生产方法以及将其用于增加植物对非生物胁迫的抗逆性和/或增加植物产量。
• Pheromone study on acarid mites. Part IX. Syntheses of alarm pheromone analogues of the mold mite, Tyrophagus putrescentiae, and their biological activities.
  作者：Yasumasa KUWAHARA、Lica SAKUMA

  DOI：10.1271/bbb1961.46.1855

  日期：——

  Against the mold mite, Tyrophagus putrescentiae, 3, 7-dimethyl-(Z)-2-octenyl formate (II) is the most active compound as an alarm pheromone besides the natural pheromone, neryl formate (I), and this activity is equal to I (1-10ppm). In order to elucidate the structural requisites for inducing alarm pheromone activity, a total of 16 analogues of I were prepared by modifying the structure of II. For preparation of 3-methyl- and 3-ethyl-(Z)-2-alkenyl formates, the Wittig reaction of ethoxy- or methoxy-carbonylmethylene triphenyl phosphorane with 2-alkanone or 3-alkanone was used. The reaction with 2-alkanone gave a mixture of (Z)-2-alkenoate (ca. 40%) and (E)-2-alkenoate (ca. 60%) in an average 60% yield. The reaction with 3-alkanone gave a mixture of (Z)-2-alkenoate (56%) and (E)-2-alkenonate (44%). Alarm pheromone activities were demonstrated on 14 compounds of (Z)-2-alkenyl formates. The presence of the (Z)-allylic primary alcohol formate moiety in a molecule was clarified as the key to induce pheromone activity, and no necessity for an acyclic monoterpene carbon skeleton was demonstrated.

  针对霉菌螨（Tyrophagus putrescentiae），3, 7-二甲基-(Z)-2-辛烯酸甲酯（II）是除了天然信息素（奈尔酸甲酯 I）外，作为警报信息素最活跃的化合物，其活性与 I 相当（1-10ppm）。为了阐明诱导警报信息素活性的结构要求，制备了16个 I 的类似物，通过改造 II 的结构。为制备3-甲基和3-乙基-(Z)-2-烯酸甲酯，采用了乙氧基或甲氧基碳酰基甲烯三苯基膦与2-烷酮或3-烷酮的威蒂格反应。与2-烷酮的反应产生了约40%的(Z)-2-烯酸酯和约60%的(E)-2-烯酸酯，平均产率为60%。与3-烷酮的反应则得到了56%的(Z)-2-烯酸酯和44%的(E)-2-烯酸酯。在14种(Z)-2-烯酸甲酯化合物中展示了警报信息素活性。研究表明，分子中存在(Z)-烯丙基初级醇酸甲酯基团是诱导信息素活性的关键，且不需要非环状单萜碳骨架。
• An entry to non-racemic β-tertiary-β-amino alcohols, building blocks for the synthesis of aziridine, piperazine, and morpholine scaffolds
  作者：Aleksandra Narczyk、Sebastian Stecko

  DOI：10.1039/d0ob01315c

  日期：——

  corresponding β,β′-dialkyl-substituted non-racemic allyl alcohols. In addition, an asymmetric synthesis of such highly substituted allylic alcohols via either enantioselective 1,2-reduction of enones, enzymatic kinetic resolution, or a functionalization of chiral propargyl alcohols, with discussion of scope and limitations of each method is reported.

  报道了一种制备具有四取代C-立体中心的对映纯 β-叔氨基醇的方法，以及将它们转化为选定的药用特权杂环系统（吗啉、氮丙啶、哌嗪）的方法。这些化合物是通过氨基甲酸烯丙酯的对映特异性σ向重排作为关键步骤获得的。后者由相应的 β,β'-二烷基取代的非外消旋烯丙醇制备。此外，还报道了通过对映选择性 1,2-烯酮还原、酶动力学拆分或手性炔丙醇功能化合成这种高度取代的烯丙醇，并讨论了每种方法的范围和局限性。