(2E)-2,6-dimethyl-2,5-heptadien-1-ol | 43160-59-4

• 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: (2E)-2,6-dimethyl-2,5-heptadien-1-ol
• 英文别名: (2E)-2,6-dimethylhepta-2,5-dien-1-ol；(E)-2,6-Dimethyl-3,5-heptadien-1-ol；(E)-2,6-dimethyl-2,5-heptadien-1-ol；(E)-2,6-dimethylhepta-2,5-dien-1-ol；(E)-2,6-dimethylhepta-2,5-dienol；(E)-(HOCH2)(CH3)CCHCH2CHC(CH3)2
• CAS: 43160-59-4；92215-03-7；43161-20-2
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: RTAAHZJTBDXDOL-RMKNXTFCSA-N

物化性质

• 沸点：
  105 °C(Press: 15 Torr)
• 密度：
  0.868±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E)-2,6-dimethyl-2,5-heptadien-1-ol 在 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 L-(+)-酒石酸二甲酯 叔丁基过氧化氢 、 四溴环己二烯-1-酮 、 四丁基氟化铵 、 氯化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (2S,3R,5S)-5-Bromo-3-chloro-2,6,6-trimethyl-tetrahydro-pyran-2-carbaldehyde
  参考文献：
  名称：

  Efficient total synthesis of the cytotoxic halogenated monoterpene aplysiapyranoid D

  摘要：

  The first total synthesis of the antitumor marine natural product aplysiapyranoid D (1d) has been accomplished in seven steps from the dienol 2 using a key brominative cyclization that gives mainly the tetrahydropyran products rather than the expected tetrahydrofuran products.

  DOI：

  10.1021/jo00004a001
• 作为产物：
  描述：

  (2,6-Dimethyl-hepta-1,5-diene-3-sulfinyl)-benzene 在 diethyl amine 作用下， 以 甲醇 为溶剂， 生成 (2E)-2,6-dimethyl-2,5-heptadien-1-ol
  参考文献：
  名称：

  从普通起始材料合成紫苏和蔷薇呋喃

  摘要：

  使用甲烯丙醇和异戊二烯氯作为常见的起始原料，合成了两种结构异构的呋喃单萜紫杉烯和蔷薇呋喃。

  DOI：

  10.1246/cl.1984.1261

文献信息

• Antiparasitic Activity of Sulfur- and Fluorine-Containing Bisphosphonates against Trypanosomatids and Apicomplexan Parasites
  作者：Tamila Galaka、Mariana Ferrer Casal、Melissa Storey、Catherine Li、María Chao、Sergio Szajnman、Roberto Docampo、Silvia Moreno、Juan Rodriguez

  DOI：10.3390/molecules22010082

  日期：——

  Based on crystallographic data of the complexes 2-alkyl(amino)ethyl-1,1-bisphosphonates–Trypanosoma cruzi farnesyl diphosphate synthase, some linear 1,1-bisphosphonic acids and other closely related derivatives were designed, synthesized and biologically evaluated against T. cruzi, the responsible agent of Chagas disease and against Toxoplasma gondii, the etiologic agent of toxoplasmosis and also towards the target enzymes farnesyl pyrophosphate synthase of T. cruzi (TcFPPS) and T gondii (TgFPPS), respectively. The isoprenoid-containing 1,1-bisphosphonates exhibited modest antiparasitic activity, whereas the linear α-fluoro-2-alkyl(amino)ethyl-1,1-bisphosphonates were unexpectedly devoid of antiparasitic activity. In spite of not presenting efficient antiparasitic activity, these data turned out to be very important to establish a structural activity relationship.

  基于2-烷基（氨基）乙基-1,1-双膦酸酯与克鲁兹锥虫法尼基二磷酸合成酶的晶体学数据，设计、合成了一些线性1,1-双膦酸及其他密切相关的衍生物，并对其在针对克鲁兹锥虫（造成查加斯病的病原体）和弓形虫（造成弓形虫病的病原体）的生物活性进行了评估，同时也针对克鲁兹锥虫（TcFPPS）和弓形虫（TgFPPS）的目标酶法尼基焦磷酸合成酶进行评估。含异戊烯基的1,1-双膦酸酯表现出适度的抗寄生虫活性，而线性α-氟-2-烷基（氨基）乙基-1,1-双膦酸酯则出人意料地缺乏抗寄生虫活性。尽管未表现出有效的抗寄生虫活性，这些数据对于建立结构活性关系却显得非常重要。
• Palladium catalyzed coupling of organostannanes with vinyl epoxides
  作者：David R. Tueting、Antonio M. Echavarren、J.K. Stille

  DOI：10.1016/0040-4020(89)80010-9

  日期：1989.1

  The coupling reaction of organotin reagents with vinyl epoxides, catalyzed by palladium, takes place at ambient temperatures, regioselectively, giving predominately the 1,4-addition product. Both aryl- and vinylstannanes undergo coupling in high yields, while acetylenic, allylic and benzylic tin reagents either give low yields or fail to couple. Although the double bond geometry in the vinylstannane

  钯催化的有机锡试剂与乙烯基环氧化物的偶联反应在环境温度下进行区域选择性的反应，主要产生1,4-加成产物。芳基和乙烯基锡烷均以高收率偶联，而炔属，烯丙基和苄基锡试剂收率较低或无法偶联。尽管在偶联产物中保持了乙烯基锡烷配偶中的双键几何形状，但是来自乙烯基环氧化物的双键几何形状是E / Z混合物。在与环状1，3-二烯单环氧化物的偶联反应中，该反应是立体异构的，有机基团从锡配偶体偶联成反式至醇官能团。
• New Syntheses of (<i>R</i>)-(+)-3-Acetoxy-2,6-dimethyl-l,5-heptadiene, the Pheromone of the Comstock Mealybug
  作者：Naoshi Nakagawa、Kenji Mori

  DOI：10.1080/00021369.1984.10866566

  日期：1984.11

  L-Phenylalanine was converted to optically impure (R)-(+)-2,6-dimethyl-1,5-heptadien-3-ol 2 (19% e.e.) .(R)-(+)-2 (96% e.e.) was prepared by a kinetic resolution of (±)-2. Acetylation of the pure (R)-(+ )- 2 gave the pheromone of the Comstock mealybug ( Pseudococcus comstockii KUWANA) [(R)-(+)-1].

  L-苯丙氨酸被转化为光学纯度不高的(R)-(+)-2,6-二甲基-1,5-七烯-3-醇2 (19% e.e.)。通过对(±)-2进行动力学分辨，制备得到了(R)-(+)-2 (96% e.e.)。纯的(R)-(+)-2经过醋酰化反应，得到了康斯托克粉虱(Pseudococcus comstockii KUWANA) 的信息素[(R)-(+)-1]。
• Synthesis of the optically active forms of 2,6-dimethyl-1, 5-heptadien-3-ol acetate, the pheromone of the comstock mealybug
  作者：K. Mori、H. Ueda

  DOI：10.1016/s0040-4020(01)98960-4

  日期：1981.1

  Both the enantiomers of 2,6-dimethyl-1,5-heptadien-3-ol acetate, the pheromone of Pseudococcus comstocki, were synthesized. The natural and dextrorotatory pheromone was proved to be the (R)-enantiomer.

  合成了2,6-二甲基-1,5-庚二烯-3-醇乙酸酯的对映体，即库氏假单胞菌的信息素。天然的和右旋的信息素被证明是（R）-对映体。
• A tellurium transposition route to allylic alcohols: overcoming some limitations of the Sharpless-Katsuki asymmetric epoxidation
  作者：Donald C. Dittmer、Robert P. Discordia、Yanzhi Zhang、Christopher K. Murphy、Archana Kumar、Aurora S. Pepito、Yuesheng Wang

  DOI：10.1021/jo00055a029

  日期：1993.1

  Good yields of enantiomeric allylic alcohols can be obtained in high enantiomeric excess (ee) by combining the Sharpless-Katsuki asymmetric epoxidation process (SAE) with tellurium chemistry. The advantages of the tellurium process are as follows: (1) the 50% yield limitation on the allylic alcohol in the Sharpless kinetic resolution (SKR) can be overcome; (2) allylic tertiary alcohols which are unsatisfactory substrates in the SKR can be obtained in high optical purity; (3) optically active secondary allylic alcohols with tertiary alkyl substituents (e.g. tert-butyl) at C-1 can be obtained in high ee; (4) optically active sterically congested cis secondary alcohols can be obtained in high ee; and (5) the nuisance of the slow SAE of some vinyl carbinols can be avoided. The key step in the reaction sequence is either a stereospecific 1,3-trans position of double bond and alcohol functionalities or an inversion of the alcohol configuration with concomitant deoxygenation of the epoxide function in epoxy alcohols. Trans secondary allylic alcohols can be converted to cis secondary allylic alcohols by way of erythro epoxy alcohols (glycidols); threo glycidyl derivatives are converted to trans secondary allylic alcohols. These transformations are accomplished by the action of telluride ion, generated in situ from the element, on a glycidyl sulfonate ester. Reduction of elemental Te is conveniently done with rongalite (HOCH2SO2Na) in an aqueous medium. This method is satisfactory when Te2- is required to attack a primary carbon site of a glycidyl sulfonate. In cases where Te2- is required to attack a secondary carbon site, reduction of the tellurium must be done with NaBH4 or LiEt3BH. Elemental tellurium is precipitated during the course of the reactions and can be recovered and reused.