(E,E)-4,8,12-Trimethyl-3,7,11-tridecatrien-1-yl iodide | 113219-28-6

• 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: (E,E)-4,8,12-Trimethyl-3,7,11-tridecatrien-1-yl iodide
• 英文别名: (3E,7E)-1-iodo-4,8,12-trimethyltrideca-3,7,11-triene；(10E)-13-iodo-2,6,10-trimethyltrideca-2,6,10-triene；homofarnesyl iodide；(E,E)-4,8,12-trimethyl-3,7,11-tridecatrienyl iodide；(E,E)-13-Iodo-2,6,10-trimethyl-2,6,10-tridecatriene；(6E,10E)-13-iodo-2,6,10-trimethyltrideca-2,6,10-triene
• CAS: 113219-28-6
• 化学式: C₁₆H₂₇I
• 分子量: 346.295
• InChiKey: DZUVOVCKRFBPCE-NCZFFCEISA-N

物化性质

• 沸点：
  348.3±31.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E,E)-4,8,12-Trimethyl-3,7,11-tridecatrien-1-yl iodide 在 叔丁基锂 作用下， 生成 (E,E)-[Ethoxy(4,8,12-trimethyl-3,7,11-tridecatrienyl)phosphinyl]formic acid, ethyl ester
  参考文献：
  名称：

  异戊烯基膦酰基甲酸酯：角鲨烯合成酶的新抑制剂。

  摘要：

  DOI：

  10.1021/jm00110a024
• 作为产物：
  描述：

  (10E)-13-bromo-2,6,10-trimethyltrideca-2,6,10-triene 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以94%的产率得到(E,E)-4,8,12-Trimethyl-3,7,11-tridecatrien-1-yl iodide
  参考文献：
  名称：

  Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase: conjugate addition of organocuprates to N-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone.

  摘要：

  Synthesis of ammonium ion analogues of the first cationic intermediate, 5, presumed to be formed during the cyclization of 2,3-oxidosqualene by 2,3-oxidosqualene-lanosterol cyclase are reported. The required 2,3-substituted-4-piperidinols are prepared by conjugate addition of higher order alkyl (2-thienyl)(cyano)cuprates to 1-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone. The nitrogen protecting group (carbobenzyloxy) is key to the synthesis in that it allows the conjugate addition to proceed in high yield and is easily converted to the required N-methyl group in the final products. The key terpenoid side chain appended to C-2 of the piperidinols was constructed from homofarnesyl bromide and 1,5-difunctionalized homoisopentenyl derivatives prepared by zirconium-catalyzed carboalumination of protected 1-butyn-4-ol.

  DOI：

  10.1021/jo00036a008

文献信息

• .alpha.-phosphonocarboxylate squalene synthetase inhibitors
  申请人：Bristol-Myers Squibb Co.

  公开号：US05312814A1

  公开（公告）日：1994-05-17

  .alpha.- Phosphonocarboxylate compounds are provided which inhibit the enzyme squalene synthetase and thereby inhibit cholesterol biosynthesis. These compounds have the formula ##STR1## wherein R.sup.1 is a lipophilic group which contains at least 7 carbons and is substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted arylalkyl or optionally substituted aryl; Z is H, halogen, hydroxy, hydroxyalkyl or lower alkyl; R.sup.2 and R.sup.3 are independently H, metal ion or other pharmaceutically acceptable cation, or a prodrug ester; R.sup.4 is H, metal ion or other pharmaceutically acceptable cation, lower alkyl, lower alkenyl, arylalkyl, aryl or a prodrug ester.

  提供了抑制齐墩果酸合酶并从而抑制胆固醇生物合成的磷酸羧酸化合物。这些化合物的化学式为##STR1##其中R.sup.1是至少含有7个碳且为取代烷基、可选择取代环烷基、可选择取代环烷基烷基、可选择取代烯基、可选择取代炔基、可选择取代芳基烷基或可选择取代芳基的亲脂基团；Z为H、卤素、羟基、羟基烷基或较低烷基；R.sup.2和R.sup.3独立地为H、金属离子或其他药用可接受阳离子，或为一种前药酯；R.sup.4为H、金属离子或其他药用可接受阳离子、较低烷基、较低烯基、芳基烷基、芳基或一种前药酯。
• Efficient route to the synthesis of C-2, C-3 substituted 4-piperidones
  作者：Dharmpal S. Dodd、Allan C. Oehlschlager

  DOI：10.1016/s0040-4039(00)79755-3

  日期：1991.7

  6-dihydro-4-pyridone ((1) has proven to be exceptionally receptive in the conjugate addition of organocuprates to give C-2 substituted piperidones having the C-3 position activated toward alkylation. Enone (1) was used as the key synthon in the synthesis of C-1, C-2 and C-3 substituted 4-piperidinol (8).

  1-Carbobenzoxy-3-carbomethoxy-5,6-dihydro-4-pyridone（（1））已被证明在共轭添加有机铜酸盐时产生了C-3取代的C-2取代的哌啶酮，C-3位置朝着烷基化方向活化。烯酮（1）被用作合成C-1，C-2和C-3取代的4-哌啶醇的关键合成子（8）。
• Farnesyl pyrophosphate analogs
  申请人：Merck & Co., Inc.

  公开号：US05298655A1

  公开（公告）日：1994-03-29

  The present invention is directed to farnesyl pyrophosphate analogs which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention, and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.

  本发明涉及抑制法尼基蛋白转移酶（FTase）和致癌基因蛋白Ras的法尼基焦磷酸酯类似物。该发明还涉及含有本发明化合物的化疗组合物，以及抑制法尼基蛋白转移酶和致癌基因蛋白Ras的方法。
• [EN] PREPARATION OF HOMOALLYLIC COMPOUNDS BY REACTION OF CYCLOPROPYLVINYL PRECURSORS WITH BRONSTEDT ACIDS<br/>[FR] PRÉPARATION DE COMPOSÉS HOMOALLYLIQUES PAR RÉACTION DE PRÉCURSEURS CYCLOPROPYLVINYLIQUES AVEC DES ACIDES DE BRÖNSTED
  申请人：GIVAUDAN SA

  公开号：WO2015059293A1

  公开（公告）日：2015-04-30

  A method of forming homoallylic compounds 2 from cyclopropylvinyl precursors 1 in the presence of a Bronsted acid HQ.

  在Bronsted酸HQ的存在下，从环丙基乙烯前体1形成同型烯丙基化合物2的方法。
• A short and selective synthesis of (S)-geranylcitronellol via conjugate addition of a functionalized copper reagent to 2-substituted exo-bornyl crotonates
  作者：Anders Johansson、Thomas Olsson、Gunnar Bergström

  DOI：10.1016/0040-4039(96)01557-2

  日期：1996.9

  An asymmetric synthesis of the diterpene (S)-geranylcitronellol 1a and its acetate 1b is reported. The chirality is induced by TMSI-promoted conjugate addition of a homoallylic monoorganocopper reagent to 2-naphthyl-exo-bornylcrotonate, which proceeds with more than 98% diastereomeric excess.

  据报道二萜（S）-香叶基香茅醇1a和其乙酸盐1b的不对称合成。手性是通过TMSI促进的将均烯丙基单有机铜试剂共轭添加到2-萘基-外-冰片基巴豆酸酯中而进行的，其非对映体过量超过98％。