1-cyclohexyl-4-methyl-pent-3-en-1-ol | 130276-75-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclohexyl-4-methyl-pent-3-en-1-ol
• 英文别名: 1-Cyclohexyl-4-methylpent-3-en-1-ol
• CAS: 130276-75-4
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: COAOPRKLMMPRAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  1-cyclohexyl-4-methyl-pent-3-en-1-ol 在 sodium hydroxide 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.83h， 生成 methyl 3-cyclohexyl-3-(benzyloxy)propanoate
  参考文献：
  名称：

  Oxidative cleavage of mono-, di-, and trisubstituted olefins to methyl esters through ozonolysis in methanolic sodium hydroxide

  摘要：

  The ozonolysis of alkenes in methanolic NaOH or NaOMe with CH2Cl2 as cosolvent leads directly to methyl esters. The procedure has been used to prepare various alpha-, beta, and omega-alkoxy esters, acyloxy esters, and alpha- and beta-N-acyl and N-sulfonyl esters from the appropriate unsaturated ethers, esters, and amides. Other examples include the formation of dimethyl octanedioate from cyclooctene (75% yield), dimethyl nonanedioate and methyl nonanoate from methyl oleate (77 and 78%, respectively), and tetradecanoic acid gamma-lactone from 2-methyl-2-hexadecen-6-ol (80% yield).

  DOI：

  10.1021/jo00066a019
• 作为产物：
  描述：

  1-溴-3-甲基-2-丁烯 、 环己烷基甲醛 在 锌 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以84%的产率得到1-cyclohexyl-4-methyl-pent-3-en-1-ol
  参考文献：
  名称：

  General and Highly α-Regioselective Zinc-Mediated Prenylation of Aldehydes and Ketones

  摘要：

  A simple, efficient, and general alpha-prenylation approach for the synthesis of a variety of alpha-prenylated alcohols has been successfully developed. A wide range of alpha-prenylated alcohol derivatives could be obtained in good yields by highly alpha-regioselective zinc-mediated prenylation of various aldehydes and ketones with prenyl bromide at 120 degrees C in HMPA. By simply altering the reaciton solvent and temperature, the method allows the achievement of a highly notable opposite regiocontrol, providing the expected regiochemical product. The method provides a convenient route for the direct alpha-prenylation of carbonyl compounds in a highly alpha-regioselective manner using a cheap and convenient mediator. Two possible pathways are proposed to account for the formation of these synthetically difficult-to-obtain molecules.

  DOI：

  10.1021/jo102516a

文献信息

• Development of a Highly α-Regioselective Metal-Mediated Allylation Reaction in Aqueous Media:  New Mechanistic Proposal for the Origin of α-Homoallylic Alcohols
  作者：Kui-Thong Tan、Shu-Sin Chng、Hin-Soon Cheng、Teck-Peng Loh

  DOI：10.1021/ja029276s

  日期：2003.3.1

  This paper described a general method to obtain α-adduct homoallylic alcohols using indium, zinc, and tin in water. A new mechanism was proposed to account for the formation of these synthetically difficult-to-obtain molecules. Generally, this method can be performed with a wide range of aldehydes and allylic halides with just 6 equiv of water added, giving the α-adduct in high selectivities. To account

  本文描述了使用水中的铟、锌和锡获得 α-加合物高烯丙醇的一般方法。提出了一种新机制来解释这些合成上难以获得的分子的形成。通常，该方法可以使用各种醛和烯丙基卤化物进行，只需添加 6 当量的水，从而以高选择性得到 α-加合物。为了解释 α-高烯丙基醇的起源，使用 1H NMR、交叉实验和 22β γ-加合物高烯丙基甾醇转化为 22α α-加合物高烯丙基甾醇的立体化学研究仔细研究了反应机理。从机理研究结果来看，金属介导的α-区域选择性烯丙基化可能存在两种机制途径共存。
• Palladium-catalysed carbonyl allylation by isoprene via regioselective 1,4-addition of tin hydride formed in situ
  作者：Yoshiro Masuyama、Megumi Tsunoda、Yasuhiko Kurusu

  DOI：10.1039/c39940001451

  日期：——

  Isoprene reacts with aldehydes in the presence of a catalytic amount of Pd(OAc)2–4PPh3 or Pd(PPh3)4 and a stoichiometric amount of SnCl2 at 40–50 °C in AcOH–H2O to produce 1-substituted 2,2-dimethyl-3-buten-1-ols regioselectively.

  异戊二烯在催化剂Pd(OAc)2-4PPh3或Pd(PPh3)4和等摩尔量的SnCl2存在下，于40-50°C的乙酸-水溶液中与醛类反应，选择性地生成1-取代的2,2-二甲基-3-丁烯-1-醇。
• Diverse Cyclization Catalyzed by In(OTf)₃ for the Convergent Assembly of Substituted Tetrahydrofurans and Tetrahydropyrans
  作者：Teck-Peng Loh、Qi-Ying Hu、Kui-Thong Tan、Hin-Soon Cheng

  DOI：10.1021/ol016228o

  日期：2001.8.1

  [GRAPHICS]A novel In(OTf)(3)-catalyzed (3,5) oxonium-ene type cyclization for the facile construction of various multisubstituted tetrahydrofurans and tetrahydropyrans was successfully developed. Further mechanistic investigations unveiled an ln(OTf)(3)-catalyzed skeletal reorganization of the tetrahydrofuran to its thermodynamic isomer under thermal conditions.
• Stereocontrolled synthesis of tetrahydrofurans and tetrahydropyrans using thallium(III)-induced cyclizations
  作者：Joseph P. Michael、Pauline C. Ting、Paul A. Bartlett

  DOI：10.1021/jo00214a003

  日期：1985.7
• Oxidative cleavage of mono-, di-, and trisubstituted olefins to methyl esters through ozonolysis in methanolic sodium hydroxide
  作者：James A. Marshall、Albert W. Garofalo

  DOI：10.1021/jo00066a019

  日期：1993.7

  The ozonolysis of alkenes in methanolic NaOH or NaOMe with CH2Cl2 as cosolvent leads directly to methyl esters. The procedure has been used to prepare various alpha-, beta, and omega-alkoxy esters, acyloxy esters, and alpha- and beta-N-acyl and N-sulfonyl esters from the appropriate unsaturated ethers, esters, and amides. Other examples include the formation of dimethyl octanedioate from cyclooctene (75% yield), dimethyl nonanedioate and methyl nonanoate from methyl oleate (77 and 78%, respectively), and tetradecanoic acid gamma-lactone from 2-methyl-2-hexadecen-6-ol (80% yield).