(1S,2S,5R)-1-烯丙基-2-异丙基-5-甲基环己醇 | 369651-27-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (1S,2S,5R)-1-烯丙基-2-异丙基-5-甲基环己醇
• 英文名称: (1R,2S,5R)-1-allylmenthol
• 英文别名: 1-Allyl-neomenthol；(1S,2S,5R)-1-allyl-2-isopropyl-5-methylcyclohexanol；(1S,2S,5R)-5-methyl-2-propan-2-yl-1-prop-2-enylcyclohexan-1-ol
• CAS: 369651-27-4
• 化学式: C₁₃H₂₄O
• 分子量: 196.333
• InChiKey: QQVOMZLQLNCNKY-AGIUHOORSA-N

物化性质

• 沸点：
  251.9±9.0 °C(Predicted)
• 密度：
  0.879±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  (1S,2S,5R)-1-烯丙基-2-异丙基-5-甲基环己醇 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 生成 2-Isopropyl-5-methyl-1-propyl-cyclohexanol
  参考文献：
  名称：

  Philippe,J. et al., Bulletin de la Societe Chimique de France, 1971, p. 2248 - 2255

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-薄荷酮 、 烯丙基溴化镁 以 四氢呋喃 为溶剂， 生成 (1S,2S,5R)-1-烯丙基-2-异丙基-5-甲基环己醇
  参考文献：
  名称：

  3-Alkyl-p-menthan-3-ol derivatives: synthesis and evaluation of their physiological cooling activity

  摘要：

  Different 3-alkyl-p-methan-3-ol derivatives provide a strong physiological cooling effect with potential application as food and cosmetic additives. In order to investigate the influence of the chemical structure on the cooling sensation, the stereoselective syntheses of 29 different 3-alkyl-p-methan-3-ol derivatives were accomplished. All the compounds obtained are odorless and were evaluated by taste, considering two sensations: a cooling effect and bitterness. The results of this structure-activity relationship study highlight that compounds with a (1R,4S)-configuration are the isomers with the more intense cooling effect and lower bitterness. In addition, the structure of the 3-alkyl chain affected the latter properties. Increasing the chain length over two carbon atoms does not change the cooling power, but enhances the bitterness with the additional feature that the branched isomers are considerably more bitter than the linear ones. Overall, the 3-alkyl-p-menthan-3-ol isomers with the best quality in terms of high cooling power and low bitterness are (1R,4S)-3-(hydroxymethyl)-p-menthan-3-ol diasteroisomers (-)-38 and (-)-42. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.022

文献信息

• Synthesis of Tetrahydrofurans by Cyclization of Homoallylic Alcohols with Iodine/Iodine(III)
  作者：Ramon S. Vasconcelos、Luiz F. Silva、Athanassios Giannis

  DOI：10.1021/jo102413u

  日期：2011.3.4

  Tetrahydrofuran derivatives can be obtained by cyclofunctionalization of homoallylic alcohols bearing a terminal double bound by using [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser’s reagent) in the presence of a catalytic amount of I2 (20 mol %) in MeOH under mild conditions. This transformation is an overall 5-endo-trig cyclization, which occurs by two different pathways. The first is a 4-exo-trig

  四氢呋喃衍生物可通过在催化量的I 2（20 mol％）在MeOH中的存在下，在催化量的I 2（20 mol％）存在下，通过使用[羟基（甲苯磺酰氧基）碘]苯（HTIB，Koser's试剂）对带有末端双键的带有末端双键的均烯丙基醇进行环官能化而获得情况。该转化是总体的5-内-trig环化，其通过两种不同的途径发生。第一个是4- exo - trig环化，然后是环扩环，而第二个是亲电加成，然后是5- endo - tet环化。
• Investigations of the Scope and Mechanism of the Tandem Hydroesterification/Lactonization Reaction
  作者：Lijun Wang、Paul E. Floreancig

  DOI：10.1021/ol048378f

  日期：2004.11.1

  alcohols and 2-pyridylmethyl formate in the presence of Ru(3)(CO)(12) initiates a tandem sequence of hydroesterification and lactonization. Mechanistic studies suggest that regioselectivity and overall reaction efficiency are governed by the relative rates of reductive elimination and beta-hydride elimination for the alkylruthenium intermediates.

  在Ru（3）（CO）（12）存在的情况下加热烯丙基和均烯丙基醇和甲酸2-吡啶基甲基甲酸酯可引发氢化酯化和内酯化的串联序列。机理研究表明，区域选择性和整体反应效率受烷基钌中间体的相对消除和β-氢化物消除的相对速率支配。
• Heteropoly Acid Supported on Silica Gel as Catalyst for the Asymmetric Transfer Allylation of Aromatic Aldehydes under Solvent-Free Conditions
  作者：Hiyoshizo Kotsuki、Shiori Nunokawa、Kazuya Oki、Keisuke Yamashita、Atsushi Okuyama、Tadaharu Ueda、Keiji Nakano、Yoshiyasu Ichikawa

  DOI：10.1055/s-0036-1588121

  日期：——

  A new convenient method for the asymmetric transfer allylation of aromatic aldehydes was developed. The reaction gave the best results using a chiral allyl donor molecule derived from (–)-menthone in the presence of heteropoly acids supported on silica gel under solvent-free conditions, and the desired homoallylic alcohol derivatives were obtained in good yields with good to high enantioselectivity

  开发了一种新的方便的芳香醛不对称转移烯丙基化方法。在无溶剂条件下，在硅胶负载的杂多酸存在下，使用衍生自 (-)-薄荷酮的手性烯丙基供体分子的反应得到了最好的结果，并且以良好的收率获得了所需的高烯丙醇衍生物。对映选择性。
• Racemization of Homoallyl Alcohols via an Allyl-transfer Reaction
  作者：Iqbal Hussain、Tatsuhiko Komasaka、Masanori Ohga、Junzo Nokami

  DOI：10.1055/s-2002-22721

  日期：——

  3-phenylpropanal 2a via an allyl-transfer reaction from a chiral allyl donor, (1R,2S,5R)-1-allylmenthol, gave (R)-1-phenylhex-5-en-3-ol 3b enantioselectively. The optical yield (ee)of (R)-3b, however, decreased with increasing chemical yield, and the chemical yield increased with increasing reaction time. The racemization takes place via an acid-catalyzed allyl-transfer reaction from (R)-3b to 2a.

  通过手性烯丙基供体 (1R,2S,5R)-1-烯丙基薄荷醇的烯丙基转移反应，酸催化 3-苯基丙醛 2a 不对称烯丙基化，得到 (R)-1-苯基己-5-en-3-ol 3b 对映选择性。然而，(R)-3b的光学产率(ee)随着化学产率的增加而降低，并且化学产率随着反应时间的增加而增加。外消旋化通过酸催化的烯丙基转移反应从 (R)-3b 到 2a 发生。
• Tandem Cross-Metathesis/Hydrogenation/Cyclization Reactions by Using Compatible Catalysts
  作者：Janine Cossy、Frédéric Bargiggia、Samir BouzBouz

  DOI：10.1021/ol027347m

  日期：2003.2.1

  [GRAPHICS]A one-pot tandem cross-metathesis/hydrogenation/cyclization procedure was achieved at room temperature, under 1 atm of hydrogen, in the presence of a ruthenium catalyst and PtO2 showing the compatibility of the two catalysts. This tandem reaction allows the synthesis of substituted lactones and lactols from acrylic acid and acrolein, respectively, in the presence of unsaturated alcohols.