Diethylgeranylphosphonate | 25996-12-7

• 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: Diethylgeranylphosphonate
• 英文别名: geranyl diethyl phosphate；diethyl (3,7-dimethylocta-2,6-dien-1-yl)phosphonate；diethyl (2E)-3,7-dimethyl-2,6-octdienylphosphonate；diethyl (2E)-3,7-dimethyl-2,6-octadienylphosphonate；(2E)-1-diethoxyphosphoryl-3,7-dimethylocta-2,6-diene
• CAS: 25996-12-7
• 化学式: C₁₄H₂₇O₃P
• 分子量: 274.34
• InChiKey: UHOQIIGZRUGIBK-SDNWHVSQSA-N

物化性质

• 沸点：
  358.9±31.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Diethylgeranylphosphonate 在 (R)-1-[2-(Ph₃Si-propargyl)naphthalene-1-yl]-2-naphthol 、 magnesium 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 79.0h， 生成 1,1,4a,7-tetramethyl-2,3,4,9,10,10a-hexahydrophenanthrene
  参考文献：
  名称：

  同型（聚异戊二烯基）芳烃的对映选择性仿生环化。(+)-Podpcarpa-8,11,13-三烯二萜和(-)-沉积源四环多戊二烯的新入口

  摘要：

  DOI：

  10.1021/ja003541x
• 作为产物：
  描述：

  芳樟醇 、 亚磷酸三乙酯 在 zinc(II) iodide 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以21%的产率得到Diethylgeranylphosphonate
  参考文献：
  名称：

  苄醇和烯丙醇直接转化为膦酸酯

  摘要：

  苄基膦酸酯通常用作 Horner-Wadsworth-Emmons 反应的试剂。在大多数情况下，它们可以从苯甲醇通过形成相应的卤化物然后进行 Arbuzov 反应来制备。为了确定更直接的膦酸酯合成方法，我们开发了一种单瓶法，通过用亚磷酸三乙酯和 ZnI 2处理将苄醇和烯丙醇转化为相应的膦酸酯。

  DOI：

  10.1021/jo200137k

文献信息

• 一种番茄红素的制备方法
  申请人：肇庆巨元生化有限公司

  公开号：CN107445791A

  公开（公告）日：2017-12-08

  本发明公开了一种番茄红素的制备方法，该制备方法以3,7‑二甲基‑1,6‑辛二烯‑磷酸二乙酯和2,6,11,15‑四甲基‑2,4,6,8,10,12,14‑十六碳七烯二醛为原料，仅需重排解离反应和缩合反应两步反应即可得到目标产物番茄红素，其反式含量高，无需再进行异构化，路线简洁、操作简单，原料来源方便、成本低，而且回收率高，适合大批量工业化生产的制备方法。
• Method of Preparing 2,6,10-Trimethyl-1,1-Dialkoxy-3,5,9-Undecatriene Used as an Intermediate of Lycopene
  申请人：ZHANG PENGFEI

  公开号：US20120316366A1

  公开（公告）日：2012-12-13

  The present invention describes a novel synthetic method for preparing the key intermediate 2,6,10-trimethyl-1,1-dialkoxy-3,5,9-undecatriene of lycopene. An existing synthetic method have some disadvantages that it is very difficult to gain the raw material dialkyl 4-methyl-5,5-diakoxy-1-pentene-1-phosphonate (10) because no effective synthetic method can be adopted, and furthermore the obtained target compound is composed of several cis/trans isomers. This invention relates to a process comprising a condensation step wherein a starting C10-phosphonate is changed to its carbanion completely at a temperature of −40˜30 under an atmosphere of a non-reactive gas in an organic solvent catalyzed by base, and then C4-dialkyl is added to undergo Wittig-Horner condensation. This invention affords all trans C14-acetal and this method is characterized with the advantages of simple procedure, easy access to raw material and low cost, which makes it has the value of industrial application.

  本发明描述了一种新颖的合成方法，用于制备番茄红素的关键中间体2,6,10-三甲基-1,1-二烷氧基-3,5,9-十一烯。现有的合成方法存在一些缺点，即很难获得原料二烷氧基-4-甲基-5,5-二烷氧基-1-戊烯-1-膦酸酯（10），因为没有有效的合成方法可采用，而且所得目标化合物由几种顄/反异构体组成。本发明涉及一种包括缩合步骤的过程，在该过程中，起始的C10-膦酸酯在非反应性气体氛围下，在有机溶剂中由碱催化完全变为其碳负离子，然后加入C4-二烷基进行威蒂-霍纳缩合。本发明提供了全顄C14-缩醛，该方法具有简单的操作程序、易获得原料和低成本的优点，使其具有工业应用的价值。
• Method of preparing 2,6,10-Trimethyl-1,1-dialkoxy-3,5,9-undecatriene used as an intermediate of lycopene
  申请人：Zhang Pengfei

  公开号：US09051254B2

  公开（公告）日：2015-06-09

  The present invention describes a novel synthetic method for preparing the key intermediate 2,6,10-trimethyl-1,1-dialkoxy-3,5,9-undecatriene of lycopene. An existing synthetic method have some disadvantages that it is very difficult to gain the raw material dialkyl 4-methyl-5,5-diakoxy-1-pentene-1-phosphonate (10) because no effective synthetic method can be adopted, and furthermore the obtained target compound is composed of several cis/trans isomers. This invention relates to a process comprising a condensation step wherein a starting C10-phosphonate is changed to its carbanion completely at a temperature of −40˜30 under an atmosphere of a non-reactive gas in an organic solvent catalyzed by base, and then C4-dialkyl is added to undergo Wittig-Horner condensation. This invention affords all trans C14-acetal and this method is characterized with the advantages of simple procedure, easy access to raw material and low cost, which makes it has the value of industrial application.

  本发明描述了一种新的合成方法，用于制备番茄红素的关键中间体2,6,10-三甲基-1,1-二烷氧基-3,5,9-十一烯。现有的合成方法存在一些缺点，即很难获得原料二烷基4-甲基-5,5-二烷氧基-1-戊烯-1-膦酸二酯（10），因为没有有效的合成方法可供采用，而且所得到的目标化合物由几个顺反异构体组成。本发明涉及一种工艺，其中在非反应性气氛下，以有机溶剂为催化剂的碱催化下，将起始C10-膦酸酯在温度为-40℃至30℃下完全转化为其碳负离子，然后加入C4-二烷基进行威特希格-霍纳缩合反应。本发明提供全部反式C14-缩醛，该方法具有工艺简单、原料易得和成本低等优点，具有工业应用价值。
• The Chemistry of Coumarin Derivatives. Part VI. Diels-Alder Trapping of 3-Methylene-2,4-chromandione. A New Entry to Substituted Pyrano[3,2-c]coumarins
  作者：Giovanni Appendino、Giancarlo Cravotto、Lucio Toma、Rita Annunziata、Giovanni Palmisano

  DOI：10.1021/jo00098a013

  日期：1994.9

  3-Methylene-2,4-chromandione (1) can be generated from dicumarol or from paraformaldehyde and 4-hydroxycoumarin. 1 is a versatile substrate for cycloaddition reactions. Depending on the reaction partner, 1 can behave as an ambident heterodiene or as a dienophile. The reaction was investigated with a series of olefins and dienes, including several isoprenoids. Some generalizations could be drawn and rationalized in terms of HOMO-LUMO interactions. The reaction of 1 and certain asymmetrically substituted olefins gives pyrano[3,2-c]coumarins in a highly regio- and chemoselective way. As an application of this reaction to natural products chemistry, a concise (three steps) synthesis of the prenylated coumarin (+/-)-isoferprenin (35a) is reported.
• KOLODYAZHNYJ, O. I.;YAKOVLEV, V. I.;GRISHKUN, E. V.;KOVALENKO, A. B.;KUXA+, DOKL. AN YCCP,(1987) N 7, 52-55
  作者：KOLODYAZHNYJ, O. I.、YAKOVLEV, V. I.、GRISHKUN, E. V.、KOVALENKO, A. B.、KUXA+

  DOI：——

  日期：——