(4-丙-1-烯-2-基环己基)甲醇 | 22451-48-5

• 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: (4-丙-1-烯-2-基环己基)甲醇
• 英文名称: (4-prop-1-en-2-ylcyclohexyl)methanol
• 英文别名: trans-dihydroperillyl alcohol；trans-8-p-menthen-7-ol；trans-shisool；trans-Skisool; trans-p-Menthen-(8)-ol-(7)；trans-4-Isopropenyl-cyclohexylmethanol
• CAS: 22451-48-5
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: GMYHXOPIKMGWOM-MGCOHNPYSA-N

物化性质

• 沸点：
  227.0±9.0 °C(Predicted)
• 密度：
  0.904±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 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

• 作为反应物：
  描述：

  (4-丙-1-烯-2-基环己基)甲醇 在 palladium on activated charcoal 氢气 、 臭氧 作用下， 生成 trans-1-(4'-hydroxymethyl-cyclohexyl)ethanone
  参考文献：
  名称：

  嗅觉中的立体化学-活性关系。包含质子供体/质子受体单元的气味

  摘要：

  描述了新型的增香剂，其中该气味与两个官能团的相互作用有关，一个是H-供体（AH功能），另一个是H-受体（B功能）。通常，仅当两个结构元件（AH / B系统）之间的距离小于3Å时，才会产生气味。对-薄荷烷和铱烷系列的双功能衍生物用作推导该规则的模型。气味感知的立体特质是其建立的重要先决条件。

  DOI：

  10.1002/hlca.19800630109
• 作为产物：
  描述：

  (S)-(-)-紫苏醛 在 glucose-6-phosphate dehydrogenase 、 D-葡萄糖-6-磷酸 、 Saccharomyces pastorianus old yellow enzyme W₁₁₆F 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 反应 26.0h， 生成 (4-丙-1-烯-2-基环己基)甲醇
  参考文献：
  名称：

  Padhi, Santosh Kumar; Bougioukou, Despina J.; Stewart, Jon D., Journal of the American Chemical Society, 2009, vol. 131, p. 3271 - 3280

  摘要：

  DOI：

文献信息

• Loop-Grafted Old Yellow Enzymes in the Bienzymatic Cascade Reduction of Allylic Alcohols
  作者：Sabrina Reich、Bettina M. Nestl、Bernhard Hauer

  DOI：10.1002/cbic.201500604

  日期：2016.4.1

  Rational loop grafting transfers enzyme properties: The reaction activity in the bienzymatic cascade reduction of allylic alcohols was successfully transferred within ene reductases by the rational exchange of two β/α surface loop regions near the entrance of the active site.

  合理的环接枝转移酶特性：通过在活性位点入口附近的两个β/α表面环区域的合理交换，烯丙基醇的双酶级联还原反应活性成功地转移到烯还原酶中。
• Monoterpene glucosides and other constituents from Perilla frutescens
  作者：Tomoyuki Fujita、Mitsuru Nakayama

  DOI：10.1016/s0031-9422(00)90843-4

  日期：1993.12

  Abstract Three new monoterpene glucosides named perilloside B-D have been isolated from the fresh leaves of Perilla frutescens. The structures were determined on the basis of spectral and chemical evidence.

  摘要 从紫苏鲜叶中分离得到了三种新的单萜苷类，命名为紫苏苷BD。基于光谱和化学证据确定结构。
• Novel Antioxidants Isolated from<i>Perilla frutescens</i>Britton var.<i>crispa</i>(Thunb.)
  作者：Tada Masahiro、Matsumoto Risa、Yamaguchi Harutaka、Chiba Kazuhiro

  DOI：10.1271/bbb.60.1093

  日期：1996.1

  Two novel antioxidants (vinyl caffeate and trans-p-menth-8-en-7-yl caffeate) and seven known antioxidants (3,4-dihydroxybenzaldehyde, methyl 3,4-dihydroxy-benzoate, methyl caffeate, 3′,4′,5,7-tetra-hydroxy-flavone, caffeic acid, 6,7-dihydroxycoumarin, and rosmarinic acid) were isolated from Perilla frutescens Britton var. crispa (Thunb.). The redox potentials of the novel isolated antioxidative compounds were comparable to those of known antioxidants. trans-p-menth-8-en-7-yl caffeate was effective to prevent the oxidative degradation of perillaldehyde in the essential oil of P. frutescens.

  两种新型抗氧化剂（乙烯基咖啡酸酯和反式对薄荷-8-烯-7-基咖啡酸酯）和七种已知抗氧化剂（3,4-二羟基苯甲醛、3,4-二羟基苯甲酸甲酯咖啡酸甲酯、3′,4′,5,7-四羟基黄酮、咖啡酸、6,7-二羟基香豆素和迷迭香酸）。crispa（Thunb.）新分离的抗氧化化合物的氧化还原电位与已知的抗氧化剂相当。反式对薄荷-8-烯-7-基咖啡酸酯能有效防止紫苏精油中紫苏醛的氧化降解。
• Stereochemical aspects of the bioreduction of the conjugated double bond of perillaldehyde
  作者：Giovanni Fronza、Claudio Fuganti、Matteo Pinciroli、Stefano Serra

  DOI：10.1016/j.tetasy.2004.08.025

  日期：2004.10

  A study on the regioselective reduction of the conjugate double bond of perillaldehyde is described. The chemical reduction of this substrate was investigated in order to provide a straightforward access to the relevant natural flavour, dihydroperill-aldehyde. The biological reduction of both natural (S)-(-)-perillaldehyde and synthetic (R)-(+)-perillaldehyde was accomplished by means of fermenting baker's yeast. The latter microorganism converted, with different diastereoselectivity, the (S)- and (R)-enantiomers into the corresponding trans and cis saturated alcohols, respectively. The origin of the hydrogen atoms added to the double bond was studied by deuterium labelling experiments and H-2 NMR measurements that clearly demonstrate a different mechanism of the biohydrogenation of the two enantiomeric forms of perillaldehyde. (C) 2004 Elsevier Ltd. All rights reserved.
• US3993604A
  申请人：——

  公开号：US3993604A

  公开（公告）日：1976-11-23

表征谱图