(Z)-4-cyclohexylbut-3-en-2-ol | 131831-40-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-4-cyclohexylbut-3-en-2-ol
• CAS: 131831-40-8
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: YZVAHJQHXUSGJH-FPLPWBNLSA-N

物化性质

• 沸点：
  220.9±8.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  α-cyclohexyl-3-methyloxiranemethanol 在 4-二甲氨基吡啶 、 碲化氢 、 sodium tetrahydroborate 、 三乙基硼氢化锂 、 sodium carbonate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (Z)-4-cyclohexylbut-3-en-2-ol
  参考文献：
  名称：

  A tellurium transposition route to allylic alcohols: overcoming some limitations of the Sharpless-Katsuki asymmetric epoxidation

  摘要：

  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.

  DOI：

  10.1021/jo00055a029

文献信息

• Telluride-mediated stereospecific conversion of racemic E-allylic alcohols to homochiral Z-allylic alcohols; transposition of primary and secondary allylic alcohols via glycidol derivatives
  作者：Robert P. Discordia、Christopher K. Murphy、Donald C. Dittmer

  DOI：10.1016/s0040-4039(00)97907-3

  日期：——

  trans-secondary allylic alcohols can be converted to homochiral cis-secondary allylic alcohols by means of a telluride-mediated transposition reaction applied to the homochiral glycidol obtained from a Sharpless kinetic resolution. (+)-Linalool is obtained in >95% enantiomeric excess from geraniol, an example of a transposition of a primary allylic alcohol to a homochiral tertiary alcohol.

  外消旋的反式仲烯丙基醇可以通过将碲化物介导的转座反应转化为同手性的顺式仲烯丙基醇，该置换反应适用于从Sharpless动力学拆分获得的同手性的缩水甘油。（+）-Linalool从香叶醇中获得> 95％的对映体过量，这是伯烯丙基醇向同手性叔醇转位的一个例子。
• DISCORDIA, ROBERT P.;MURPHY, CHRISTOPHER K.;DITTMER, DONALD C., TETRAHEDRON LETT., 31,(1990) N9, C. 5603-5606
  作者：DISCORDIA, ROBERT P.、MURPHY, CHRISTOPHER K.、DITTMER, DONALD C.

  DOI：——

  日期：——