(Z)-4,8-dimethylnona-3,7-dienal | 76826-74-9

• 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: (Z)-4,8-dimethylnona-3,7-dienal
• 英文别名: (3Z)-4,8-dimethylnona-3,7-dienal
• CAS: 76826-74-9
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: AEMBVQYDXXTMIH-FLIBITNWSA-N

物化性质

• 沸点：
  245.1±19.0 °C(Predicted)
• 密度：
  0.855±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  (Z)-4,8-dimethylnona-3,7-dienal 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以654 mg的产率得到homonerol
  参考文献：
  名称：

  Stereoselective Synthesis of Homoneryl and Homogeranyl Triazole Bisphosphonates

  摘要：

  Isoprenoid-substituted bisphosphonates are known to serve as inhibitors of the enzyme geranylgeranyl diphosphate synthase, and their activity can be highly sensitive to olefin stereochemistry. A mixture of homogeranyl and homoneryl triazole bisphosphonates has previously demonstrated potent activity, and thus stereocontrolled syntheses of the individual isomers have been developed.

  DOI：

  10.1021/acs.joc.6b01693
• 作为产物：
  描述：

  (Z)-2-acetoxy-2-acetyl-5,9-dimethyldeca-4,8-dienoic acid tert-butyl ester 在 sodium periodate 、 lithium aluminium tetrahydride 、 silica gel 、 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 52.0h， 生成 (Z)-4,8-dimethylnona-3,7-dienal
  参考文献：
  名称：

  Stereoselective Synthesis of Homoneryl and Homogeranyl Triazole Bisphosphonates

  摘要：

  Isoprenoid-substituted bisphosphonates are known to serve as inhibitors of the enzyme geranylgeranyl diphosphate synthase, and their activity can be highly sensitive to olefin stereochemistry. A mixture of homogeranyl and homoneryl triazole bisphosphonates has previously demonstrated potent activity, and thus stereocontrolled syntheses of the individual isomers have been developed.

  DOI：

  10.1021/acs.joc.6b01693

文献信息

• Amides as bioisosteres of triazole-based geranylgeranyl diphosphate synthase inhibitors
  作者：Daniel B. Goetz、Michelle L. Varney、David F. Wiemer、Sarah A. Holstein

  DOI：10.1016/j.bmc.2020.115604

  日期：2020.8

  synthase (GGDPS) inhibitors are of potential therapeutic interest as a consequence of their activity against the bone marrow cancer multiple myeloma. A series of bisphosphonates linked to an isoprenoid tail through an amide linkage has been prepared and tested for the ability to inhibit GGDPS in enzyme and cell-based assays. The amides were designed as analogues to triazole-based GGDPS inhibitors. Several

  香叶基香叶基二磷酸合酶 (GGDPS) 抑制剂因其对骨髓癌多发性骨髓瘤的活性而具有潜在的治疗意义。已经制备了一系列通过酰胺键连接到类异戊二烯尾部的双膦酸盐，并在基于酶和细胞的测定中测试了抑制 GGDPS 的能力。酰胺被设计为类似于基于三唑的 GGDPS 抑制剂。几种新化合物在酶和细胞测定中均显示出 GGDPS 抑制活性，其效力取决于链长和烯烃立体化学。
• Palladium-catalyzed formylation of organic halides with carbon monoxide and tin hydride
  作者：Victor P. Baillargeon、J. K. Stille

  DOI：10.1021/ja00263a015

  日期：1986.2

  La formylation catalysee par le palladium d'une variete de substrats organiques (iodoarenes, halogenures benzyliques, iodures vinyliques, triflates de vinyles et halogenures allyliques) avec le tributylstannane et le monoxyde de carbone donne les aldehydes avec de bons rendements dans des conditions douces et tolere un certain nombre de groupes fonctionnels

  La formylation catalysee par le palladium d'une variete de substrats Organics特定的团体名称
• Three-Carbon Homologating Agent: New Preparation of (3,3-Diisopropoxypropyl)triphenylphosphonium Bromide
  作者：Jacques Viala、Maurice Santelli

  DOI：10.1055/s-1988-27589

  日期：——

  A new and very efficient preparation of the title compound in one step using acrolein, triphenylphosphine and hydrobromic acid is described. This reagent used in the three-carbon homologation of carbonyl compounds gave β,γ-unsaturated aldehydes in good yields.

  报道了一种新的高效率一步合成标题化合物的方法，使用丙烯醛、三苯基膦和氢溴酸。该试剂在羰基化合物的三碳同系化反应中，能以良好的产率得到β,γ-不饱和醛。
• Organic syntheses with sulfones noxxxvi: conversion of sulfones into aldehydes and ketones.
  作者：J.-B. Baudin、M. Julia、C. Rolando

  DOI：10.1016/s0040-4039(00)95090-1

  日期：1985.1

  Alkyl and allyl sulfones can be converted into boronic esters, oxidation of which leads to aldehydes or ketones.

  烷基和烯丙基砜可转化为硼酸酯，其氧化可生成醛或酮。
• Use of certain manganese-accumulating plants for carrying out organic chemistry reactions
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US10702860B2

  公开（公告）日：2020-07-07

  The use, after heat treatment, of manganese accumulating plants for carrying out chemical reactions.

  利用经过热处理的蓄锰植物进行化学反应。