ethyl nona-2,3-dienoate | 928835-59-0

• 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 nona-2,3-dienoate
• 英文别名: Nona-2,3-dienoic acid, ethyl ester
• CAS: 928835-59-0
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: RSGLOEHCQDOWGS-UHFFFAOYSA-N

物化性质

• 沸点：
  243.7±7.0 °C(Predicted)
• 密度：
  0.885±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  ethyl nona-2,3-dienoate 在 吡啶 、 Tebbe's reagent 、 三丁基膦 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  通过分支反应途径实现多样性：多环支架的生成和抗迁移剂的鉴定

  摘要：

  通过一系列膦催化的成环反应、Tebbe 反应、Diels-Alder 反应以及某些情况下的水解，合成了由 16 个不同支架组成的 91 种杂环化合物库。这种以多样性为导向的合成努力产生了一系列化合物，这些化合物在立体化学和所代表的支架范围方面都表现出高水平的结构变化。因此，一个简单但强大的反应序列产生了一个相对适中的高度多样性库，用于探索化学空间的生物学相关区域。从该文库中，鉴定出几种抑制乳腺癌细胞迁移和侵袭的分子，并可作为抗转移剂开发的先导物。

  DOI：

  10.1002/chem.201002195
• 作为产物：
  描述：

  1-diazoheptan-2-one 、 乙氧甲酰基亚甲基三苯基膦 在 silver benzoate 作用下， 生成 ethyl nona-2,3-dienoate
  参考文献：
  名称：

  Long-acting contraceptive agents: Norethisterone esters of polyunsaturated acids

  摘要：

  Some new derivatives of norethisterone (17 alpha-ethynyl-17 beta-hydroxyestr-4-en-3-one) are described in which the 17 beta-hydroxyl group of the steroid is esterified with polyunsaturated aliphatic acids. The potential of these compounds as long-acting contraceptive agents has been evaluated.

  DOI：

  10.1016/0039-128x(83)90098-3

文献信息

• Phosphine-Catalyzed β-Selective Conjugate Addition of α-Fluoro-β-ketoamides to Allenic Esters
  作者：Narendra Kumar Vaishanv、Mohd Khalid Zaheer、Ruchir Kant、Kishor Mohanan

  DOI：10.1002/ejoc.201901199

  日期：2019.9.22

  A strategy for the β‐selective conjugate addition of α‐fluoro‐β‐ketoamides to allenic esters has been developed via phosphine catalysis and demonstrated for a wide range of ketoamides and allenoate substrates.

  通过膦催化，已经开发了一种将α-氟-β-酮酰胺添加到烯丙基酯中的β-选择共轭的策略，并已证明可用于多种酮酰胺和烯丙基酸酯底物。
• Substrate-controlled, PBu₃-catalyzed annulation of phenacylmalononitriles with allenoates enables tunable access to cyclopentenes
  作者：Narendra Kumar Vaishanv、Sanoop P Chandrasekharan、Mohd Khalid Zaheer、Ruchir Kant、Kishor Mohanan

  DOI：10.1039/d0cc04688d

  日期：——

  phenacylmalononitriles with allenoates, controlled by the γ-substitution on allenoates, offers a tunable synthesis of multifunctionalized cyclopentene carboxamides and cyclopentenols. An unprecedented formation of cyclopentene carboxamide was observed when allenic esters bearing a substitution at the γ-position were employed, while unsubstituted allenoates produced cyclopentenols. The former reaction likely involves

  在PBu 3催化的[3 + 2]苯甲酰丙二腈与脲基酸酯的环化反应中的差异，由脲基酸酯上的γ取代控制，提供了多官能化环戊烯羧酰胺和环戊烯醇的可调谐合成。当使用在γ位带有取代基的烯丙基酯时，观察到空前的环戊烯羧酰胺形成，而未取代的烯醇酸酯产生环戊烯醇。前一种反应可能以多米诺骨牌方式涉及迈克尔/醛/亲核环化序列。
• Direct Catalytic Asymmetric and Regiodivergent N1‐ and C3‐ Allenylic Alkylation of Indoles
  作者：Taochun Zha、Jiehui Rui、Zhihan Zhang、Dongqiang Zhang、Zhirong Yang、Peiyuan Yu、Yingcheng Wang、Fangzhi Peng、Zhihui Shao

  DOI：10.1002/anie.202300844

  日期：——

  We report the first direct catalytic asymmetric N1-functionalization of 1H-indoles via an allenylic alkylation strategy. This transformation produces N-alkylated indoles bearing axial chirality with a stereocenter non-adjacent (β) to the nitrogen. The regioselectivity (N1/C3) of this process can be switched efficiently. We also introduce a new class of tri-substituted allenylic electrophiles.

  我们报告了第一个通过烯丙基烷基化策略对 1H-吲哚进行直接催化不对称 N1-功能化。这种转化产生具有轴向手性的 N-烷基化吲哚，其立构中心不与氮相邻 (β)。该过程的区域选择性 (N1/C3) 可以有效切换。我们还介绍了一类新的三取代丙二烯基亲电子试剂。
• Small-Molecule Inhibitors of Protein Geranylgeranyltransferase Type I
  作者：Sabrina Castellano、Hannah D. G. Fiji、Sape S. Kinderman、Masaru Watanabe、Pablo de Leon、Fuyuhiko Tamanoi、Ohyun Kwon

  DOI：10.1021/ja070274n

  日期：2007.5.1

  Small molecules that inhibit the geranylgeranylation of K-Ras4B and RhoA by protein geranylgeranyltransferase type I (GGTase-I) were identified from chemical genetic screens of heterocycles synthesized through phosphine catalysis of allenes. To further improve the efficacy of the GGTase-I inhibitors (GGTIs), 4288 related compounds bearing core dihydropyrrole/pyrrolidine and tetrahydropyridine/piperidine scaffolds were synthesized on SynPhase lanterns in a split-pool manner through phosphine-catalyzed [3 + 2] and [4 + 2] annulations of resin-bound allenoates. Testing of the 4288 analogues resulted in several GGTIs exhibiting submicromolar IC50 values. Because proteins such as Ras and Rho GTPases are implicated in oncogenesis and metastasis, these GGTIs might ultimately lead to the development of novel antitumor therapeutics.
• Iron Porphyrin-Catalyzed Olefination of Ketenes with Diazoacetate for the Enantioselective Synthesis of Allenes
  作者：Chuan-Ying Li、Xiao-Bing Wang、Xiu-Li Sun、Yong Tang、Jun-Cheng Zheng、Zheng-Hu Xu、Yong-Gui Zhou、Li-Xin Dai

  DOI：10.1021/ja068642v

  日期：2007.2.1

  In the presence of Ph3P and catalytic Fe(TCP) Cl, ketenes could react with EDA to give allenes in high yields under neutral conditions for the first time. By employing chiral phosphine instead of PPh3, allenes could be synthesized with high enantioselectivity (93-98% ee) in good yields.