(1R,2S,5R)-1-vinyl-2-iso-propyl-5-methylcyclohexan-1-ol | 33651-06-8

• 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,2S,5R)-1-vinyl-2-iso-propyl-5-methylcyclohexan-1-ol
• 英文别名: (1R,2S,5R)-2-isopropyl-5-methyl-1-vinylcyclohexan-1-ol；1-Vinyl-neomenthol；(1R,2S,5R)-1-ethenyl-5-methyl-2-propan-2-ylcyclohexan-1-ol
• CAS: 33651-06-8
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: YDBXKKDNIGMCKC-WOPDTQHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (1R,2S,5R)-1-vinyl-2-iso-propyl-5-methylcyclohexan-1-ol 在 吡啶 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 (1S,2S,5R)-1-hydroxy-2-isopropyl-5-methylcyclohexane-1-carbaldehyde
  参考文献：
  名称：

  [EN] SUBSTITUTED CYCLOHEXANECARBOXAMIDES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
  [FR] CYCLOHEXANECARBOXAMIDES SUBSTITUÉS, LEUR PRÉPARATION ET LEUR APPLICATION THÉRAPEUTIQUE

  摘要：

  式（1）的化合物中，其中R1表示-C（R2）（R3） - [C（R4）（R5）] m-L-R6基团或-R7；以及式（1）的化合物的制备和治疗用途，作为TRPM8受体的激动剂，特别适用于治疗口咽吞咽困难。

  公开号：

  WO2022133027A1
• 作为产物：
  描述：

  (R)-menthol 在 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (1R,2S,5R)-1-vinyl-2-iso-propyl-5-methylcyclohexan-1-ol
  参考文献：
  名称：

  [EN] SUBSTITUTED CYCLOHEXANECARBOXAMIDES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
  [FR] CYCLOHEXANECARBOXAMIDES SUBSTITUÉS, LEUR PRÉPARATION ET LEUR APPLICATION THÉRAPEUTIQUE

  摘要：

  式（1）的化合物中，其中R1表示-C（R2）（R3） - [C（R4）（R5）] m-L-R6基团或-R7；以及式（1）的化合物的制备和治疗用途，作为TRPM8受体的激动剂，特别适用于治疗口咽吞咽困难。

  公开号：

  WO2022133027A1

文献信息

• 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。
• Regio‐ and Diastereoselective Rhodium‐Catalyzed Allylic Substitution with Unstabilized Benzyl Nucleophiles
  作者：Debasis Pal、Timothy B. Wright、Ryan O'Connor、P. Andrew Evans

  DOI：10.1002/anie.202008071

  日期：2021.2.8

  rhodium‐catalyzed allylic substitution of challenging alkyl‐substituted secondary allylic carbonates with benzylzinc reagents, which are prepared from widely available benzyl halides. This process utilizes rhodium(III) chloride as a commercially available, high‐oxidation state and bench‐stable pre‐catalyst to provide a rare example of a regio‐ and diastereoselective allylic substitution in the absence of an

  我们开发了具有高度区域选择性和非对映选择性的铑催化的具有挑战性的烷基取代的仲碳酸烯丙酯的苄基锌取代烯丙基碳酸酯，该苄基锌试剂由可广泛获得的苄基卤化物制得。该方法利用氯化铑（III）作为市售的高氧化态和稳定的预催化剂，提供了在缺乏外源配体的情况下区域和非对映选择性烯丙基取代的罕见实例。该反应可耐受电子多样性的苄基锌亲核试剂和一系列功能化和/或挑战性的脂族烯丙基亲电试剂。最后，利用铑-烯丙基中间体的构型通量性开发了一种新的非对映选择性过程，用于构建邻近的无环三元/三元立体发生中心，
• 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.
• A nonresolutive approach to the preparation of configurationally pure difunctional molecules
  作者：Sandra Chillous、David J. Hart、Douglas K. Hutchinson

  DOI：10.1021/jo00148a046

  日期：1982.12
• Chiral aminoalcohols with a menthane skeleton as catalysts for the enantioselective addition of diethylzinc to benzaldehyde
  作者：Stefan Panev、Anthony Linden、Vladimir Dimitrov

  DOI：10.1016/s0957-4166(01)00206-3

  日期：2001.6

  Novel chiral aminoalcohols were synthesized by highly diastereoselective addition of Me3SiCN and LICH2CN to (-)-menthone followed by LiAlH4 reduction. The addition of CH2=CH-MgBr and PhCH=CH-MgBr to menthone and the following epoxidation, provided useful hydroxy epoxides, one of which could be aminolyzed to afford an aminodiol. In one case, the configuration of the newly formed epoxidic stereogenic center was determined by X-ray crystallography. When applied as catalysts in the enantioselective addition of Et2Zn to benzaldehyde, the aminoalcohols induced enantiomeric excesses (e.e.s) of up to 77%. (C) 2001 Elsevier Science Ltd. All rights reserved.