4-甲氧基环己-3-烯-1-醇 | 69125-55-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-甲氧基环己-3-烯-1-醇
• 中文别名: 4-甲氧基-3-环己烯-1-醇
• 英文名称: 4-hydroxy-1-methoxy-1-cyclohexene
• 英文别名: 4-hydroxy-1-methoxycyclohex-1-ene；4-hydroxy-1-methoxy-cyclohexene；4-methoxy-3-cyclohexen-1-ol；4-methoxycyclohex-3-en-1-ol；1-methoxycyclohexen-4-ol；4-Methoxy-3-cyclohexenol
• CAS: 69125-55-9
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: MXTVFVQEKZRVHS-UHFFFAOYSA-N

物化性质

• 沸点：
  234 ºC
• 密度：
  1.03
• 闪点：
  103 ºC

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2909499000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-甲氧基环己-3-烯-1-醇 在 咪唑 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.75h， 生成 4-[[(1,1-二甲基乙基)二苯基甲硅烷基]氧基]-环己酮
  参考文献：
  名称：

  Studies of vitamin D (calciferol) and its analogs. 44. Thermal [1,7]-sigmatropic shift of previtamin D3 to vitamin D3: synthesis and study of pentadeuterio derivatives

  摘要：

  Specifically pentadeuteriated previtamin D3 11 has been synthesized to impart thermal stability to the otherwise labile material. A 12-step synthesis of the trideuteriated A-ring 14b from p-methoxyphenol was developed and employed the addition of (methyl-d3)magnesium iodide to either the keto thiomethylene intermediate 23 or the keto dioxane 27. The enantiomerically pure trideuterio A-ring (-)-14b was then coupled with the deuteriated CD fragment 13b followed by hydrogenation to afford pentadeuteriated previtamin D3 11. A primary deuterium kinetic isotope effect (KIE) study of the [1,7]-sigmatropic hydrogen migration in the conversion of previtamin D3 to vitamin D3 indicated a more ''normal'' primary deuterium isotope effect (as compared to a previously reported literature value of approximately 45). At 80-degrees-C, a k(H)/k(D) for the previtamin D3 to vitamin D3 isomerization was determined to be approximately 6.2. At 25-degrees-C, this [1,7]-sigmatropic hydrogen migration proceeds with a k(H)/k(D) Of approximately 11.4. The reversible, first-order [1,7]-sigmatropic hydrogen shift of previtamin D3 to D3, determined over the temperature range 60.1-85.5-degrees-C is characterized by the following activation parameters: log A(H) = 8.8 and E(a)H = 19.6 kcal/mol. Deuteriated pre-D3, which rearranges over this temperature range, is characterized by the activation parameters log A(D) = 9.5 and E(a)D = 21.9 kcal/mol.

  DOI：

  10.1021/jo00055a011
• 作为产物：
  描述：

  4-甲氧基苯酚 在 氨 、 lithium 作用下， 生成 4-甲氧基环己-3-烯-1-醇
  参考文献：
  名称：

  异喹啉鎓盐合成三环萘[b]稠合骨架

  摘要：

  环酮的烯醇醚与异喹啉鎓盐的环加成是常规制备有趣的三环萘衍生物的关键步骤。

  DOI：

  10.1016/s0040-4039(01)80800-5

文献信息

• Imidazo heterocyclic compounds
  申请人：——

  公开号：US20010049385A1

  公开（公告）日：2001-12-06

  A novel class of imidazo heterocyclic compounds, pharmaceutical compositions comprising them and use thereof in the treatment and/or prevention of diseases and disorders related to the histamine H3 receptor. More particularly, the compounds are useful for the treatment and/or prevention of diseases and disorders in which an interaction with the histamine H3 receptor is beneficial.

  一种新型的咪唑杂环化合物类，包括它们的药物组合物以及它们在治疗和/或预防与组胺H3受体相关的疾病和紊乱中的应用。更具体地说，这些化合物对于治疗和/或预防需要与组胺H3受体相互作用有益的疾病和紊乱是有用的。
• Process for the preparation of monoketals of 1,4-cyclohexanedione including 1, 4-cyclohexanedione mono-2,2-dimethyl trimethylene ketal
  申请人：DR. REDDY'S LABORATORIES LIMITED

  公开号：US20040230063A1

  公开（公告）日：2004-11-18

  There is provided a process for preparation of a monoketal compound of the structure 1 that includes reacting 1,4-cyclohexanedione of the structure 2 with a diol of the structure 3 in a halogenated organic solvent in the presence of an acid catalyst, wherein X is a substituted or unsubstituted ethylene or propylene. Various embodiments and variants are provided.

  提供了一种制备结构1的单酮化合物的方法，包括在卤代有机溶剂中，在酸催化剂的存在下，将结构2的1,4-环己二酮与结构3的二元醇反应，其中X是取代或未取代的乙烯或丙烯。提供了各种实施方式和变体。
• Total Synthesis of Aeruginosin 98B
  作者：Barry M. Trost、Toshiyuki Kaneko、Neil G. Andersen、Christoph Tappertzhofen、Bruce Fahr

  DOI：10.1021/ja309947n

  日期：2012.11.21

  The first total synthesis of aeruginosin 98B was accomplished. The key step is a highly diastereoselective Pd-catalyzed intramolecular asymmetric allylic alkylation reaction of a diastereomeric mixture of allylic carbonates that is enabled by the use of racemic phosphine ligand L1.

  完成了铜绿素98B的首次全合成。关键步骤是高度非对映选择性 Pd 催化的烯丙基碳酸酯非对映异构混合物的分子内不对称烯丙基烷基化反应，该反应通过使用外消旋膦配体 L1 实现。
• Total synthesis of (±)-androst-4-en-3-one-17-carboxylic acid
  作者：Jih Ru Hwu、Eric Jan Leopold

  DOI：10.1039/c39840000721

  日期：——

  The synthesis of the title compound (1) has been accomplished via the polycyclization of epoxide (7d) having an enol acetate as a terminator.

  标题化合物（1）的合成已经通过具有烯醇乙酸酯作为终止剂的环氧化物（7d）的多环化而完成。
• Stille–Heck Coupling Sequences Applied in a Versatile New Access to Steroid Skeletons
  作者：Hans Wolf Sünnemann、Anja Hofmeister、Jörg Magull、Armin de Meijere

  DOI：10.1002/chem.200601240

  日期：2007.4.27

  an interesting 7-carboxyl-substituted steroidal dienone. Attempts to remove the remaining protecting groups from some of the other new steroidal compounds under acidic conditions furnished a novel 3-oxo-7-carboxyl steroid analogue and a 3-hydroxy-substituted steroidal diene. A novel estradiol derivative could be obtained in 69% yield from the synthesized steroidal dienone. Deprotection furnished the

  利用一系列的Stille和Heck交叉偶联反应以及随后的热6pi-电环化反应，合成了多种对映体纯的甾体化合物。在几个2-溴环己-1-烯基三氟甲磺酸酯的三氟甲磺酸酯部分上具有顺式和反式稠合双环[4.3.0]壬烯基锡烷酸酯的高度化学选择性Stille偶联提供了相应的三环溴丁二烯，收率高至优异（70-97％）。将它们与丙烯酸叔丁酯进行Heck反应以提供五取代的三环1,3,5-己三烯。通过在Pd（OAc）2和P（o-Tol）3与加成的三芳基膦作为共配体的情况下制备的Palladacycle的基础上，将新的方案与预催化剂一起使用，可以实现效率的显着提高（产率73-90％） ）。在十氢化萘中加热到205-215摄氏度或在甲苯中加热到140摄氏度（对于某些情况）后，这些六三烯生成（78-90％）各种不饱和类固醇类似物，为单一非对映异构体。在将相邻的羰基脱保护后获得的特定氧代己三烯，在140℃的异常低温下