methyl (Z)-2-carbomethoxy-5,9-dimethyl-4,8-decadienoate | 60729-61-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (Z)-2-carbomethoxy-5,9-dimethyl-4,8-decadienoate
• 英文别名: Methyl (Z)-2-methoxycarbonyl-5,9-dimethyldeca-4,8-dienoate；2-(3,7-diemthylocta-2Z,6-dienyl)malonic acid dimethyl ester；dimethyl (Z)-2-(3,7-dimethylocta-2,6-dien-1-yl)malonate；dimethyl 2-[(2Z)-3,7-dimethylocta-2,6-dienyl]propanedioate
• CAS: 60729-61-5
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: MSQDGYGYNAXYOI-XFXZXTDPSA-N

物化性质

• 沸点：
  125-130 °C(Press: 0.1 Torr)
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-carbomethoxy-5,9-dimethyl-4,8-decadienoate 在 吡啶 、 lithium aluminium tetrahydride 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 50.0h， 生成 [(4Z)-5,9-dimethyldeca-4,8-dienyl] methanesulfonate
  参考文献：
  名称：

  Bishomoisoprenoid triazole bisphosphonates as inhibitors of geranylgeranyl diphosphate synthase

  摘要：

  Protein geranylgeranylation reactions are dependent on the availability of geranylgeranyl diphosphate (GGDP), which serves as the isoprenoid donor. Inhibition of GGDP synthase (GGDPS) is of interest from a drug development perspective as GGDPS inhibition results in impaired protein geranylgeranylation, which in multiple myeloma, disrupts monoclonal protein trafficking and induces apoptosis. We have recently reported a series of isoprenoid triazole bisphosphonates and have demonstrated that a 3:1 mixture of homogeranyl and homoneryl isomers potently, and in a synergistic manner, inhibits GGDPS. We now present the synthesis and biological evaluation of a novel series of bishomoisoprenoid triazoles which furthers our understanding of the structure-function relationship of this class. These studies demonstrate the importance of chain length and olefin stereochemistry on inhibitory activity. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.066
• 作为产物：
  描述：

  在 锌 作用下， 以 溶剂黄146 为溶剂， 生成 methyl (Z)-2-carbomethoxy-5,9-dimethyl-4,8-decadienoate
  参考文献：
  名称：

  Cyclobutenes作为金（I）催化的1,8-烯炔的环异构化中的可分离中间体

  摘要：

  Abstractmagnified imageThe gold(I)‐catalysed isomerisation of 1,8‐enynes allows the efficient synthesis of functionalised bicyclo[5.2.0]nonenes. Notably, these cyclobutenes derivatives can be isolated as reactive intermediates that could undergo subsequent gold(I)‐catalysed transformations such as isomerisation, fragmentation or ene reaction to furnish more structurally complex products. This study also provides useful information related to the mechanism leading to metathesis‐type derivatives, examples of which were shown to be produced, in the present case, by a gold(I)‐catalysed ring fragmentation of the cyclobutene moiety.

  DOI：

  10.1002/adsc.200900056

文献信息

• Molybdenum(0) and tungsten(0) catalysts with enhanced reactivity for allylic substitution: regioselectivity and solvent effects †
  作者：Andrei V. Malkov、Ian R. Baxendale、Darren J. Mansfield、Pavel Kočovský

  DOI：10.1039/b100903f

  日期：——

  have been developed as pre-catalysts for allylic substitution with β-dicarbonyl nucleophiles. These complexes are reduced in situ to Mo(0) and W(0) catalytic species 30a,b and 31a,b by excess of NaH, employed to generate sodiomalonate nucleophiles, or by DIBAL-H. 1,3-Dioxolane and 1,4-dioxane, when used as solvents, substantially accelerate the reaction. These new catalysts exhibit “traditional” Mo regiochemistry

  已开发出双核Mo（II）和W（II）配合物28a，b和29a，b作为用β-二羰基亲核试剂进行烯丙基取代的预催化剂。这些络合物通过过量的NaH原位还原为Mo（0）和W（0）催化物种30a，b和31a，b，或用于DIBAL-H，该NaH用于生成磺基丙二酸酯亲核试剂。当用作溶剂时，1，3-二氧戊环和1，4-二氧六环大大促进了反应。这些新的催化剂表现出“传统的”区域化学，即，亲核攻击优先发生在取代度更高的碳上（5  →  9 ; 37  →  38），除非像香叶烷基那样，另外一个因素（例如与烯丙基亲电试剂的另一个部分进一步配位）会参与（41）型基板（32或33  →  36）。
• ELECTROPHILIC REACTION OF ALLYL ACETATES WITH ELECTROGENERATED CARBANIONS IN THE PRESENCE OF Pd(0)-CATALYST
  作者：Makoto Minato、Tsutomu Nonaka、Toshio Fuchigami

  DOI：10.1246/cl.1986.1071

  日期：1986.7.5

  Counter cation effect on the Pd(0)-catalyzed electrophilic reaction of allyl acetates with carbanions was studied by using the electrogenerated carbanions having various kinds of counter cations.

  利用具有多种抗衡阳离子的电生碳负离子，研究了抗衡阳离子对乙酸烯丙酯与碳负离子的Pd(0)催化亲电反应的影响。
• A convenient procedure for smooth palladium-catalyzed allylic alkylation by sodium dimethyl malonate and cyclopentadienide. A new synthesis of allylic substituted cyclopentadienes.
  作者：J.C. Fiaud、J.L. Malleron

  DOI：10.1016/s0040-4039(00)92193-2

  日期：——

  The use of the Pd(dba)12/dpe catalytic system in allylic alkylation allows sodium dimethyl malonate to react with allylic acetates at room temperature. According to this procedure, a novel synthesis of allylic substituted cyclopentadienes is described through the use of cyclopentadienide anion as a nucleophile.

  在烯丙基烷基化中使用Pd（dba）1 2 / dpe催化体系可使丙二酸二甲酯钠在室温下与乙酸烯丙酯反应。根据该方法，描述了通过使用环戊二烯阴离子作为亲核试剂来合成烯丙基取代的环戊二烯的新方法。
• Stereospecific Indium(III)‐Catalysed Tandem Cycloisomerization of Functionalized 1,6‐enynes: Scope and Mechanistic Insights
  作者：Raquel Pérez‐Guevara、Luis A. Sarandeses、Rosana Álvarez、M. Montserrat Martínez、José Pérez Sestelo

  DOI：10.1002/adsc.202301329

  日期：2024.2.20

  structures by cationic cascade reactions using aryl 1,6-enynes (Scheme 1b).16 In these contributions, the superior catalytic activity of diiodoindium(III) cation (InI2+), generated by the addition of Ag(I) salts to InI3, was discovered. In this article we report on the stereospecific indium(III)-catalysed tandem cycloisomerization reactions of functionalized 1,6-enynes to access a variety of polycyclic

  介绍 亲碳路易斯酸催化活化碳-碳不饱和键（π酸催化）是现代有机化学中日益重要的合成工具。1这种金属催化的亲电活化为构建在天然产物合成和材料科学中有价值的新碳键提供了一种原子和步骤经济、通用且高效的方法。2通常，催化作用与铂或金等贵重过渡金属有关，3然而，镓或铟等主族金属已被认为是经济的替代品。4铟作为第 13 族元素，具有极具吸引力的化学性质，具有广阔的合成应用前景。5作为具有亲氧和亲碳特性的软路易斯酸，铟(III) 具有σ-和π-酸的双重催化活性以及优异的官能团耐受性。6多年来，其催化活性已被用作基本有机转化（例如羰基加成或 Diels-Alder 反应）中的 σ-酸，5也被用作碳-碳不饱和键（主要是炔烃）的氢官能化中的 π-酸。6, 7作为我们对铟化学长期研究的一部分，8我们已经报道了在分子内炔烃加氢芳基化、加氢烷氧基化和加氢胺化反应中以及最近在 1,5-烯炔环异构化反应中使用铟 (III)
• Allylic alkylation. Palladium-catalyzed substitutions of allylic carboxylates. Stereo- and regiochemistry
  作者：Barry M. Trost、Thomas R. Verhoeven

  DOI：10.1021/ja00534a029

  日期：1980.7