<1R>-5(R)-methyl-2(S)-<1(S)-methyl-2-hydroxyethyl>cyclohexanol | 13834-08-7

• 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
• 英文名称: <1R>-5(R)-methyl-2(S)-<1(S)-methyl-2-hydroxyethyl>cyclohexanol
• 英文别名: (1R,2S,5R)-2-[(S)-2'-hydroxy-10-methylethyl]-5-methylcyclohexan-1-ol；(1R,2S,5R)-2-((S)-1-hydroxypropan-2-yl)-5-methylcyclohexanol；(-)-(1R,3R,4S,8S)-p-menthane-3,9-diol；(-)-(1R,3R,4S,8S)-menthane-3,9-diol；(1R,3R,4S,8S)-3,9-p-menthanediol；(-)-(1R,3R,4S,8S)-p-Menthan-3,9-diol；(1R,2S,5R)-2-[(2S)-1-hydroxypropan-2-yl]-5-methylcyclohexan-1-ol
• CAS: 13834-08-7
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: BINZTUGHCIRHLP-DOLQZWNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <1R>-5(R)-methyl-2(S)-<1(S)-methyl-2-hydroxyethyl>cyclohexanol 在 potassium permanganate 作用下， 以 乙酸乙酯 为溶剂， 生成 (3S,3aS,6R,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone
  参考文献：
  名称：

  对-薄荷烷内酯的合成及感官特性

  摘要：

  描述了对-薄荷烷内酯7a - h的立体选择性合成和感官特性。除了更正有关这些化合物的公开数据外，这项工作还明确鉴定了Italo Mitcham黑色薄荷油（Mentha piperita）中的7a，7b和7g。另外，这些内酯由于其异常的气味强度和典型的香豆素样香气，在香水工业中引起了极大的兴趣。

  DOI：

  10.1016/s0040-4020(00)00397-5
• 作为产物：
  描述：

  (-)-(1R,3R,4S)-p-menth-8(10)-ene-3,9-diol 在 镍 氢气 作用下， 以 甲醇 为溶剂， 生成 <1R>-5(R)-methyl-2(S)-<1(S)-methyl-2-hydroxyethyl>cyclohexanol
  参考文献：
  名称：

  非对映异构体（1 R）-Diboran异构体

  摘要：

  模具Umsetzung DER stereoisomeren Isopulegole 1 - 4 MIT乙硼烷erfolgt温特达赫Stereospezifität。Aus der nachfolgenden oxydativen Aufarbeitung resultieren die Gemische der 9-Hydroxymenthole，in denes eines der Diastereomeren starküberwiegt。Die Konstitution von 7 Diolen（5 – 11）世界遗产组织和综合组织。

  DOI：

  10.1002/hlca.19670500123

文献信息

• Regioselective free radical phenylsulfenation of a non-activated δ-carbon atom by the photolysis of alkyl benzenesulfenate
  作者：Goran Petrović、Radomir N Saičić、Živorad Čeković

  DOI：10.1016/s0040-4020(02)01477-1

  日期：2003.1

  A regioselective free radical introduction of a phenylthio group onto a non-activated δ-carbon atom was achieved by photolysis of alkyl benzenesulfenates in the presence of hexabutylditin, and δ-phenylthio alcohols were obtained in 35–91% yields. δ-Phenylsulfenylation of a non-activated carbon atom induced only by irradiation of alkyl benzenesulfenates (without initiation by hexabutylditin) also occurs

  在六丁基二锡的存在下，通过烷基苯磺酸盐的光解作用，将苯硫基的区域选择性自由基引入到未活化的δ-碳原子上，并以35-91％的产率获得了δ-苯硫醇。也发生仅由烷基苯磺酸盐的辐照引起的未活化碳原子的δ-苯磺酰化（未由六丁基二锡引发），但是观察到反应速度较慢，且δ-苯硫醇的收率较低。
• Pheromone syntheses: A tropical approach. Enantioselective synthesis of the (2R,6S,10S) and (2S,6S,10S) isomers of methyl 2,6,10-trimethyldodecanoate
  作者：J.Tércio B. Ferreira、Paulo H.G. Zarbin

  DOI：10.1016/0968-0896(96)00015-6

  日期：1996.3

  The enantioselective syntheses of two stereoisomers, (2R,6S,10S) and (2S,6S,10S), of methyl 2,6,10-trimethyldodecanote, out of eight possible isomers, are described , employing the stereoselective hydroboration of (-)-isopulegol (2) and (+)-neo-isopulegol (2a) as the key reaction.

  描述了使用（-）的立体选择性氢硼化反应，从八种可能的异构体中，合成了2,6,10-三甲基十二烷基甲基的两个立体异构体（2R，6S，10S）和（2S，6S，10S）的对映选择性合成-异异薄荷醇（2）和（+）-新异异薄荷醇（2a）作为关键反应。
• STEREOSELECTIVE SYNTHESIS OF PERHYDRO-3,6-DIALKYL-2-BENZO[B]FURANONES AND ANALOGS
  申请人：International Flavors & Fragrances Inc.

  公开号：US20200377466A1

  公开（公告）日：2020-12-03

  Synthetic methods of preparing perhydro-3,6-dimethyl-2-benzo[b]furanones, in particular dihydromintlactone, and analogs through reaction of dehydrogenation of menthanediols and analogs with a base in the presence of (carbonylchlorohydrido[bis-(2-diphenylphosphinoethyl)amine]ruthenium(II) as catalyst in good stereoselectivity and yields under stereochemistry controlled conditions are disclosed.

  本发明揭示了一种通过对蒎烷二醇及其类似物进行脱氢反应，与碱在(carbonylchlorohydrido[bis-(2-diphenylphosphinoethyl)amine]ruthenium(II)催化剂的存在下，以良好的立体选择性和产率控制条件下，合成过氢化3,6-二甲基-2-苯并[b]呋喃酮类化合物，特别是二氢薄荷内酯及其类似物的合成方法。
• The constitutents of Schizonepeta tenuifolia Briq. I. Structures of two new monoterpene glucosides, Schizonepetosides A and B.
  作者：HIROSHI SASAKI、HEIHACHIRO TAGUCHI、TOHRU ENDO、ITIRO YOSIOKA、YOICHI IITAKA

  DOI：10.1248/cpb.29.1636

  日期：——

  Two new glucosides, named schizonepetosides A (1) and B (2), were isolated from the spikes of Schizonepeta tenuifolia (Labiatae). The structure of 1 was elucidated as (1S, 4R, 8E)-9-O-β-D-glucopyranosyl-p-menth-8 (9)-en-3-one on the basis of chemical and spectral studies. Compound 2 was identified as a glucoside possessing a dioxane ring formed by the double linkage between glucose and the aglycone, (1S, 4R, 8R)-8, 9-dihydroxy-p-menth-3-one, by X-ray crystallographic analysis.

  从 Schizonepeta tenuifolia（唇形科植物）的穗状花序中分离出了两种新的苷类，分别命名为 schizonepetosides A (1) 和 B (2)。根据化学和光谱研究，阐明了 1 的结构为 (1S, 4R, 8E)-9-O-β-D-Glucopyranosyl-p-menth-8 (9)-en-3-one 。通过 X 射线晶体学分析，确定化合物 2 是一种葡萄糖苷，具有由葡萄糖和苷元 (1S，4R，8R)-8，9-二羟基-对薄荷-3-酮之间的双链所形成的二氧环。
• Stereoselective synthesis of perhydro-3,6-dialkyl-2-benzo[b]furanones and analogs
  申请人：International Flavors & Fragrances Inc.

  公开号：US10995080B2

  公开（公告）日：2021-05-04

  Synthetic methods of preparing perhydro-3,6-dimethyl-2-benzo[b]furanones, in particular dihydromintlactone, and analogs through reaction of dehydrogenation of menthanediols and analogs with a base in the presence of (carbonylchlorohydrido[bis-(2-diphenylphosphinoethyl)amine]ruthenium(II) as catalyst in good stereoselectivity and yields under stereochemistry controlled conditions are disclosed.

  本发明公开了在立体化学受控条件下，以羰基氯氢[双-(2-二苯基膦乙基)胺]钌(II)为催化剂，通过门冬烷二醇和类似物与碱的脱氢反应制备全氢-3,6-二甲基-2-苯并[b]呋喃酮，特别是二氢薄荷内酯和类似物的合成方法，具有良好的立体选择性和收率。