(2S-顺)-四氢化-4-甲基-2-(2-甲基-1-丙烯基)-2H-吡喃 | 3033-23-6

• 物质功能分类: 有机原料 - 醚类化合物及其衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: (2S-顺)-四氢化-4-甲基-2-(2-甲基-1-丙烯基)-2H-吡喃
• 中文别名: 左旋玫瑰醚；4-甲基-2-(2-甲基-1-丙烯基)四氢吡喃
• 英文名称: (2S,4R)-4-methyl-2-(2-methyl-1-propenyl)tetrahydropyran
• 英文别名: (-)-cis-rose oxide；(2S,4R) rose oxide；cis-(-)-rose oxide；cis-rose oxide；rose oxide；(2S)-4c-Methyl-2r-(2-methyl-propenyl)-tetrahydro-pyran；(2S,4R)-4-methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran；(2S,4R)-4-methyl-2-(2-methylprop-1-enyl)oxane
• CAS: 3033-23-6
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: CZCBTSFUTPZVKJ-NXEZZACHSA-N

物化性质

• 沸点：
  70-71 °C12 mm Hg(lit.)
• 密度：
  0.871 g/mL at 20 °C(lit.)
• 闪点：
  68 °C
• 溶解度：
  Very slightly soluble in water, soluble in alcohol and oils
• LogP：
  3.13
• 物理描述：
  colourless mobile liquid, powerful, distinctive geranium top note
• 折光率：
  1.453-1.457

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/38
• 海关编码：
  2932999099
• 安全说明：
  S26,S61

反应信息

• 作为反应物：
  描述：

  (2S-顺)-四氢化-4-甲基-2-(2-甲基-1-丙烯基)-2H-吡喃 在 臭氧 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.25h， 生成 (-)-(2S,4R,E)-Sesquirose oxide
  参考文献：
  名称：

  氧化玫瑰合成倍半乳糖

  摘要：

  由四种光学活性的玫瑰氧化物1至4制备八种立体异构的倍半玫瑰氧化物9至16。给出了光谱数据，旋光度和9至16的嗅觉特性。

  DOI：

  10.1002/hlca.19800630627
• 作为产物：
  描述：

  3,6-dihydro-4-methyl-2H-pyran-2-carboxylic acid 在 铂 氯化亚砜 、 硫酸 、 氢气 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (2S-顺)-四氢化-4-甲基-2-(2-甲基-1-丙烯基)-2H-吡喃
  参考文献：
  名称：

  Structure Elucidation, Enantioselective Analysis, and Biogenesis of Nerol Oxide in Pelargonium Species

  摘要：

  A novel enantioselective synthesis of nerol oxide (3,6-dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran) was used for the determination of the absolute configuration at C-2. The order of elution of the enantiomers on octakis-(2,3-di-O-butyryl-6-O-tert-butyldimethylsilyl)-gamma-cyclodextrin in OV 1701-vi as the chiral stationary phase in enantioselective GC was determined as (2R) before (2S). Enantioselective multidimensional GC/MS (enantio-MDGC/MS) was used for the determination of the enantiomeric ratios of nerol oxide in different geranium oils. As a result, in all investigated oils nerol oxide occurs as a racemate. The biogenesis of nerol oxide in Pelargonium species was investigated by feeding experiments using deuterium-labeled neryl glucoside as the precursor. The Pelargonium plants were able to convert the fed precursor into racemic nerol oxide, which has to be considered as a "natural racemate"

  DOI：

  10.1021/jf981245m

文献信息

• METHOD FOR PRODUCING CIS-ROSE OXIDE
  申请人：Koenigsmann Lucia

  公开号：US20100311988A1

  公开（公告）日：2010-12-09

  The present invention relates to a process for the preparation of cis-2-(2-methylprop-1-enyl)-4-methyltetrahydropyran comprising the catalytic hydrogenation of 2-(2-methylprop-1-enyl)-4-methylenetetrahydropyran in the presence of hydrogen and a heterogeneous catalyst comprising ruthenium on a support and subsequently bringing the compounds obtained in this way into contact with a strongly acidic cation exchanger.

  本发明涉及一种制备顺式-2-(2-甲基丙-1-烯基)-4-甲基四氢吡喃的方法，包括在氢气和一种包含钌负载在载体上的非均相催化剂存在下，对2-(2-甲基丙-1-烯基)-4-亚甲基四氢吡喃进行催化加氢，然后将以这种方式获得的化合物与强酸性阳离子交换树脂接触。
• PROCESS FOR THE PREPARATION OF CIS-ROSE OXIDE
  申请人：BASF SE

  公开号：US20130109867A1

  公开（公告）日：2013-05-02

  The present invention relates to a process for the preparation of a composition enriched in cis-2-(2-methylprop-1-enyl)-4-methyltetrahydropyran, comprising the catalytic hydrogenation of 2-(2-methylprop-1-enyl)-4-methylenetetrahydropyran in the presence of hydrogen and a heterogeneous catalyst comprising ruthenium.

  本发明涉及一种制备富含顺式-2-(2-甲基丙-1-烯基)-4-甲基四氢吡喃的组合物的方法，包括在氢气和包含钌的非均相催化剂存在下对2-(2-甲基丙-1-烯基)-4-亚甲基四氢吡喃进行催化加氢。
• [EN] METHOD FOR PRODUCING DEHYDRO ROSE OXIDE<br/>[FR] PROCÉDÉ DE PRODUCTION D'OXYDE DE ROSE DÉSHYDRO
  申请人：BASF SE

  公开号：WO2014184311A1

  公开（公告）日：2014-11-20

  The present invention relates to a method for producing dehydro rose oxide by reacting isoprenol and prenal in the presence of at least one sulfonic acid of formula R1-SO3H as catalyst, wherein R1 is selected from phenyl which carries 2 or 3 C1-C4-alkyl substituents, phenyl which carries one C8-C20-alkyl substituent and optionally also 1 or 2 C1-C4-alkyl substituents, and naphthyl which optionally carries 1 or 2 C1-C4-alkyl substituents.

  本发明涉及一种通过在至少一种式为R1-SO3H的磺酸催化剂存在下使异戊醇和前香叶醛反应制备脱氢玫烯氧化物的方法，其中R1选自携带2或3个C1-C4烷基取代基的苯基，携带一个C8-C20烷基取代基并且还可以选择性地携带1或2个C1-C4烷基取代基的苯基，以及选择性地携带1或2个C1-C4烷基取代基的萘基。
• COMPOUNDS FOR PREVENTING, REDUCING AND/OR ALLEVIATING ITCHY SKIN CONDITION(S)
  申请人：SCHMAUS Gerhard

  公开号：US20160008297A1

  公开（公告）日：2016-01-14

  The present invention primarily relates to the use of one or more specific compounds and/or one or more respective salt(s) thereof for preventing, reducing or alleviating itchy skin condition(s), and/or as PAR-2 antagonist. Furthermore, the present invention relates to compositions (products or, respectively, formulations), in particular for topical administration, preferably cosmetic or pharmaceutical compositions, in particular for preventing, reducing or alleviating one or more itchy skin conditions and/or for providing a PAR-2 antagonistic effect, comprising or consisting of an effect amount of such compound(s) and/or salt(s) and one or more cosmetically and/or pharmaceutically acceptable carriers.

  本发明主要涉及使用一种或多种特定化合物和/或其一个或多个相应盐来预防、减少或缓解瘙痒皮肤状况，和/或作为PAR-2拮抗剂。此外，本发明涉及组合物（产品或相应的配方），特别是用于局部给药，优选为化妆品或药用组合物，特别是用于预防、减少或缓解一种或多种瘙痒皮肤状况和/或产生PAR-2拮抗作用的组合物，包括或由效果量的这种化合物和/或盐以及一个或多个化妆品和/或药用可接受载体组成。
• Synthesis and odor of optically active rose oxide
  作者：Takeshi Yamamoto、Hiroyuki Matsuda、Yasuhide Utsumi、Toshimitsu Hagiwara、Tsuneyoshi Kanisawa

  DOI：10.1016/s0040-4039(02)02311-0

  日期：2002.12

  Stereoselective synthesis of optically active rose oxide (1) by KHSO4 and Pd–BINAP-catalyzed cyclization of (3R)- and (3S)-3,7-dimethyl-6,7-octadien-1-ol (5) is described. One-pot synthesis of the (3R)- and (3S)-allenyl alcohol 5 from (3R)- and (3S)-citronellol (2) (98% ee) is also described. Furthermore, the odor properties of the four diastereomers of 1 are reported.

  KHSO 4和Pd–BINAP催化的（3 R）-和（3 S）-3,7-二甲基-6,7-辛二烯-1-醇（5）的立体选择性合成旋光性氧化玫瑰（1）描述。所述（3一锅法合成- [R ）-和（3小号）-allenyl醇5从（3 - [R ）-和（3小号） -香茅醇（2）（98％ee）的也被描述。此外，还报道了四种非对映异构体1的气味特性。

表征谱图