1-(4-methylcyclohexyl)but-3-en-1-ol | 24580-63-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-methylcyclohexyl)but-3-en-1-ol
• 英文别名: 4-Methyl-1-(prop-2-EN-1-YL)cyclohexan-1-OL；4-methyl-1-prop-2-enylcyclohexan-1-ol
• CAS: 24580-63-0
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: GAZLBGCMWZBMAG-UHFFFAOYSA-N

物化性质

• 沸点：
  204.3±9.0 °C(Predicted)
• 密度：
  0.901±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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-(4-methylcyclohexyl)but-3-en-1-ol 在 sodium hydroxide 、 硼烷 、 双氧水 、 potassium carbonate 、 对甲苯磺酰氯 作用下， 以 吡啶 为溶剂， 反应 28.0h， 生成 8-Methyl-1-oxaspiro<4.5>decane
  参考文献：
  名称：

  Terpenes and terpene derivatives - XV. [1 ] Synthesis of 4,8-dimethyl-2-(2-methyl-1-propenyl)--1-oxaspiro(4.5]dec-7-ene (“bisabolene oxide”)

  摘要：

  DOI：

  10.1016/s0040-4020(01)91487-5
• 作为产物：
  描述：

  烯丙基三丁基锡 、 4-甲基环己酮 在 碘 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.0h， 以83%的产率得到1-(4-methylcyclohexyl)but-3-en-1-ol
  参考文献：
  名称：

  Efficient Synthesis of Homoallylic Alcohols/Amines from Allyltributylstannane and Carbonyl Compounds/Imines Using Iodine as Catalyst Under Acetic Acid–Water Medium

  摘要：

  This paper describes a general method for the synthesis of homoallylic alcohols and amines by nucleophilic addition reaction of allyltributylstannane to carbonyl compounds and aldimines where iodine acts as a catalyst in H2O/acetic acid (1:1) medium. Only 10mol% of I-2 is required for various organic transformations. By using this process, various homoallylic alcohols and amines are produced in good to excellent yields.

  DOI：

  10.1080/00397911.2015.1085574

文献信息

• Hydroxyl Group-Assisted Palladium-Catalyzed Lactonization of Homoallylic Alcohols
  作者：Liangbin Huang、Qian Wang、Wanqing Wu、Huanfeng Jiang

  DOI：10.1002/cctc.201300903

  日期：2014.2

  of α‐methylene‐γ‐lactones through the palladium(II)‐catalyzed lactonization of homoallylic alcohols with alkynamides has been reported. The hydroxyl group in the terminal olefins cooperates with the amide in alkynamides to promote the cyclization by suppressing the β‐H elimination. This process provides a route to construct naturally occurring biologically multifunctional α‐methylene‐γ‐lactones.

  据报道，通过钯（II）催化均烯丙基醇与炔酰胺的内酯化，可以方便高效地合成α-亚甲基-γ-内酯。末端烯烃中的羟基与炔基酰胺中的酰胺协同作用，通过抑制β-H的消除来促进环化。该过程提供了构建天然存在的生物多功能α-亚甲基-γ-内酯的途径。
• [bmim][Br] as an Inexpensive and Efficient Medium for the Barbier-Type Allylation Reaction Using a Catalytic Amount of Indium: Mechanistic Studies
  作者：Papiya Dey、Mrunesh Koli、Dibakar Goswami、Anubha Sharma、Subrata Chattopadhyay

  DOI：10.1002/ejoc.201800043

  日期：2018.3.22

  The Barbier‐type allylation of aldehydes and ketones can be carried out with both unsubstituted and γ‐substituted allyl bromides using only a catalytic amount (0.1 equiv.) of In metal in [bmim][Br].

  醛和酮的Barbier型烯丙基化反应可以在[bmim] [Br]中仅使用催化量（0.1当量）的In金属与未取代和γ-取代的烯丙基溴进行。
• SnCl2·2H2O-mediated Barbier-type allylation: A comparative evaluation of the catalytic performance of CuI and Pd(OAc)2
  作者：Pabitra Kumar Kalita、Prodeep Phukan

  DOI：10.1016/j.crci.2013.02.012

  日期：2013.11

  Résumé A systematic investigation has been carried out for the allylation of carbonyl compounds under SnCl2·2H2O-mediated Barbier-type conditions, using CuI and Pd(OAc)2 as catalysts. Ketones, which are not reactive under the influence of CuI, however, could be activated by using Pd(OAc)2 as a catalyst. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.pdf

  简要概述 在SnCl2·2H2O介导的Barbier类型条件下，对羰基化合物进行系统研究，使用CuI和Pd(OAc)2作为催化剂。在CuI的影响下不具反应性的酮类化合物，可以通过使用Pd(OAc)2作为催化剂进行活化。 补充材料： 本文的补充材料作为一个单独的文件提供：mmc1.pdf
• Allylation of cyclohexanones in aqueous media and influence of facial amphiphilic fructopyranosides
  作者：Ana Bellomo、Richard Daniellou、Daniel Plusquellec

  DOI：10.1016/j.tetlet.2010.07.028

  日期：2010.9

  The indium-catalyzed allylation reaction was performed in good yields and short reaction time with various cyclohexanones in water. Aqueous facial amphiphilic carbohydrates solutions were also screened for their potency to modify the stereochemical outcome of the reaction. (C) 2010 Elsevier Ltd. All rights reserved.
• Rapid access to homoallylic alcohols via Pd(OAc)2 catalyzed Barbier type allylation in presence of DMAP
  作者：Bishwapran Kashyap、Prodeep Phukan

  DOI：10.1016/j.tetlet.2013.09.038

  日期：2013.11

  DMAP was found to accelerate significantly the rate of Pd(OAc)(2) catalyzed Barbier type allylation of carbonyl compounds by allylbromide using SnCl2 center dot 2H(2)O as reducing agent. Both aldehyde as well as ketones produced excellent yields within a short reaction time in the presence of 3 mol % of Pd(OAc)(2) and 12 mol % of DMAP at room temperature. Aldehydes could be allylated within 5-10 min whereas, in case of ketones, the reaction completes in 45-120 min. (C) 2013 Elsevier Ltd. All rights reserved.