(5E)-nonen-4-ol | 121440-80-0

• 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: (5E)-nonen-4-ol
• 英文别名: (E)-Non-5-en-4-ol
• CAS: 121440-80-0
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: AGJGJUGBPXOLEG-SOFGYWHQSA-N

物化性质

• 沸点：
  197.4±8.0 °C(Predicted)
• 密度：
  0.843±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (5E)-nonen-4-ol 在 吡啶 、 三氯化磷 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以2.2 g的产率得到6-chloro-trans-4-nonene
  参考文献：
  名称：

  镍/去氧麻黄碱络合物催化的活化和未活化仲烷基卤的Hiyama反应。

  摘要：

  DOI：

  10.1002/anie.200700440
• 作为产物：
  描述：

  Toluene-4-sulfonic acid (S)-1-((2S,3R)-3-propyl-oxiranyl)-butyl ester 在 碲化氢 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(5E)-nonen-4-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

• syn stereocontrol in the directed dihydroxylation of acyclic allylic alcohols
  作者：Timothy J. Donohoe、Nicholas J. Newcombe、Michael J. Waring

  DOI：10.1016/s0040-4039(99)01371-4

  日期：1999.9

  The preparation and directed dihydroxylation of a series of acyclic allylic alcohols is reported. The oxidation reaction is capable of demonstrating high levels of diastereoselection for the syn isomer. An explanation of the observed selectivities based on the degree of allylic strain is presented and a transition state model proposed.

  报道了一系列无环烯丙基醇的制备和直接二羟基化。该氧化反应是能够展示高水平diastereoselection为的顺式异构体。提出了基于烯丙基应变的程度观察到的选择性的解释，并提出了过渡状态模型。
• Molybdenum-Catalyzed Diastereoselective <i>anti</i>-Dihydroxylation of Secondary Allylic Alcohols
  作者：Shixia Su、Chuan Wang

  DOI：10.1021/acs.orglett.9b00735

  日期：2019.4.5

  In this protocol, we report a Mo-catalyzed anti-dihydroxylation of secondary allylic alcohols, providing a general method for the preparation of 1,2,3-triols bearing up to three continuous stereocenters with excellent diastereocontrol. The mechanistic studies reveal that this dihydroxylation reaction consists of two steps and up to excellent diastereomeric ratios of the final triol products can be

  在该协议中，我们报告了钼催化的仲烯丙基醇的抗二羟基化作用，为制备具有多达三个连续立体中心的1,2,3-三醇提供了出色的非对映异构控制的一般方法。机理研究表明，该二羟基化反应包括两个步骤，并且由于初始环氧化中的非对映控制和随后的原位水解中的区域控制都很高，因此最终三醇产物的非对映异构体比例可以达到极高的水平。
• 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。
• Ligand-controlled cobalt-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes
  作者：Pei Zhao、Jiaxin Huang、Jie Li、Kezhuo Zhang、Wen Yang、Wanxiang Zhao

  DOI：10.1039/d1cc05964e

  日期：——

  The Co-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes were realized by a ligand-controlled strategy. The remote hydroboration with dcype provided borylethers, while xantphos favored the formation of silyl enol ethers.

  烯丙基硅氧烷的共催化远程硼氢化和烯烃异构化是通过配体控制的策略实现的。用 dcype 进行远程硼氢化反应提供硼醚，而 xantphos 有利于形成甲硅烷基烯醇醚。
• The synthesis of 6,6,6-2H3-2E-hexenal
  作者：Simon Fielder、Daryl D. Rowan

  DOI：10.1002/jlcr.2580340214

  日期：1994.2

  6,6,6-2H3-2E-Hexenal, leaf-aldehyde, has been synthesized in 45% yield and 99.3% purity by reaction of 3,3,3-2H3-n-propyl magnesium bromide with an ethereal solution of 3-trimethylsiloxy-2-propenal (3) prepared in situ. This new one pot procedure alleviates the need to isolate (3) and should prove useful in the synthesis of other E-α,β-unsaturated aldehydes.

  通过 3,3,3-2H3- 正丙基溴化镁与原位制备的 3-三甲基硅氧基-2-丙烯醛（3）的乙醚溶液反应，合成了 6,6,6-2H3-2E-己烯醛（叶醛），收率为 45%，纯度为 99.3%。这一新的一锅法简化了(3)的分离过程，在合成其他 E-α,β-不饱和醛类化合物时也会很有用。