(2,2,4-trimethyl-3-cyclohexen-1-yl)methanol | 55695-33-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,2,4-trimethyl-3-cyclohexen-1-yl)methanol
• 英文别名: (2,2,4-trimethyl-3-cyclohexenyl)methanol；2,2,4-trimethyl-3-cyclohexenylmethanol；(+/-)-2.2.4-trimethyl-1-hydroxymethyl-cyclohexene-(3)；(+/-)-2.2.4-Trimethyl-1-hydroxymethyl-cyclohexen-(3)；2.2.4-Trimethylcyclohex-3-enmethanol；(2,2,4-Trimethylcyclohex-3-en-1-yl)methanol
• CAS: 55695-33-5
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: XPYOIEYPDVHLNN-UHFFFAOYSA-N

物化性质

• 沸点：
  113-113.5 °C(Press: 13 Torr)
• 密度：
  0.9293 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2,2,4-trimethyl-3-cyclohexen-1-yl)methanol 在 N-甲基吗啉 、 PPL (SIGMA type II) from Porcine pancreas 作用下， 以 乙醚 、 正己烷 、 异丙醚 、 甲苯 为溶剂， 反应 120.0h， 生成 (E)-3-((S)-2,2,4-Trimethyl-cyclohex-3-enylmethoxy)-acrylic acid methyl ester
  参考文献：
  名称：

  Synthesis of both enantiomers of cis-α-irone and cis-γ-irone, principal constituents of iris oil, via resolution of (±)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acid

  摘要：

  The principal constituents of iris oil, (-)-cis-alpha -irone and (-)-cis-gamma -irone, and their enantiomers, were synthesized from (-)- and (+)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acids. The racemic acid was resolved by recrystallization of its salt with a chiral amine, or by enzymatic hydrolysis of the corresponding alcohol. The fragrances of (-)-(1R,SS)-cis-alpha -irone and (-)-(1R,SS)-cis-gamma -irone were superior to those of (+)-(1S,5R)-cis-alpha -irone and (+)-(1S,5R)-cis-gamma -irone. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00345-1
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 aluminum isopropoxide 、 异丙醇 作用下， 生成 (2,2,4-trimethyl-3-cyclohexen-1-yl)methanol
  参考文献：
  名称：

  合成von 1,1,5-Trimethyl-2-oxymethyl-cyclohexen-（4）

  摘要：

  1,1,5-Trimethyl-2-oxymethyl-cyclohexen-（4）wurde合成dargestellt。本质上讲。

  DOI：

  10.1002/hlca.19510340425

文献信息

• [EN] OPSIN-BINDING LIGANDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] LIGANDS LIANT L'OPSINE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：BIKAM PHARMACEUTICALS INC

  公开号：WO2013081642A1

  公开（公告）日：2013-06-06

  Compounds and compositions are disclosed that are useful for treating ophthalmic conditions caused by or related to production of toxic visual cycle products that accumulate in the eye, such as dry adult macular degeneration, as well as conditions caused by or related to the misfolding of mutant opsin proteins and/or the mis-localization of opsin proteins. Compositions of these compounds alone or in combination with other therapeutic agents are also described, along with therapeutic methods of using such compounds and/or compositions. Methods of synthesizing such agents are also disclosed.

  揭示了用于治疗由于或与在眼睛中积聚的有毒视觉循环产物有关的眼科疾病的化合物和组合物，例如干性成人黄斑变性，以及由于或与突变视蛋白的错误折叠和/或视蛋白的错误定位有关的疾病。还描述了这些化合物单独或与其他治疗剂的组合物，以及使用这些化合物和/或组合物的治疗方法。还揭示了合成这些药剂的方法。
• A Stereoselective Synthesis of (±)-<i>cis-γ</i>-Irone
  作者：Cornelius Nussbaumer、Georg Fráter

  DOI：10.1002/hlca.19880710315

  日期：1988.5.4

  (±)-cis-γ-Irone(1), a main constitutent of natural iris oil, has been stereoselectively synthesized from methyl (2E)-3 -[(2,2,4-trimethyl-3-cyclohexen-1-yl)methoxy]-2-propenoate (3) (6 steps, overall yield 14%). The cis-configuration as the exocyclic position of the double bond of 1 were secured by the thermal ene reaction of the β-(alkenyloxy)acrylate 3 yielding the 3-oxabicyclo [3,3,1] nonane derivative

  天然虹膜油的主要成分（±）-顺式-γ- Irone（1）是由甲基（2 E）-3-[（2,2,4-三甲基-3-环己烯-1- ））（6），总产率为14％）。通过β-（烯基氧基）丙烯酸酯3的热烯反应，得到3-氧杂双环[3,3,1]壬烷衍生物5，确保作为1的双键的环外位置的顺式构型。
• The Relationship between Structure and Odor in the Case of Certain Derivatives of 2,2,4-Trimethyl-Δ³-cyclohexene Aldehyde¹
  作者：Olga N. Jitkow、Marston T. Bogert

  DOI：10.1021/ja01852a055

  日期：1941.7
• Lauchenauer; Schinz, Helvetica Chimica Acta, 1949, vol. 32, p. 1273
  作者：Lauchenauer、Schinz

  DOI：——

  日期：——
• Stereoselective synthesis of (.+-.)-cis-.alpha.-irone
  作者：Cornelius Nussbaumer、Georg Frater

  DOI：10.1021/jo00386a038

  日期：1987.5