(R)-(+)-2,6-dimethyl-1,5-heptadien-3-ol | 80232-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(+)-2,6-dimethyl-1,5-heptadien-3-ol
• 英文别名: (3R)-2,6-Dimethylhepta-1,5-dien-3-ol
• CAS: 80232-52-6
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: CSASCUZDIRYDDE-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：

  (R)-(+)-2,6-dimethyl-1,5-heptadien-3-ol 、 乙酸酐 在 吡啶 作用下， 反应 14.0h， 以90%的产率得到(R)-(+)-2,6-dimethyl-1,5-heptadien-3-ol acetate
  参考文献：
  名称：

  Larcheveque, Marc; Petit, Yves, Bulletin de la Societe Chimique de France, 1989, # 1, p. 130 - 139

  摘要：

  DOI：
• 作为产物：
  描述：

  (2E)-2,6-dimethyl-2,5-heptadien-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 、 溶剂黄146 、 sodium iodide 、 锌 作用下， 以 吡啶 、 二氯甲烷 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 31.5h， 生成 (R)-(+)-2,6-dimethyl-1,5-heptadien-3-ol
  参考文献：
  名称：

  合成2,6-二甲基-1、5-庚二烯-3-醇乙酸酯（comstock粉虱的信息素）的旋光形式

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(01)98960-4

文献信息

• 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。
• Stereospecific telluride-mediated conversion of glycidols to allyl alcohols: an extension of the Sharpless kinetic resolution
  作者：Robert P. Discordia、Donald C. Dittmer

  DOI：10.1021/jo00292a004

  日期：1990.3
• LARCHEVEQUE, MARC;PETIT, YVES, BULL. SOC. CHIM. FR.,(1989) N, C. 130-139
  作者：LARCHEVEQUE, MARC、PETIT, YVES

  DOI：——

  日期：——
• 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.