1-(phenylethynyl)-2-methylcyclohexan-1-ol | 24580-49-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(phenylethynyl)-2-methylcyclohexan-1-ol
• 英文别名: 2-methyl-1-(2-phenylethynyl)cyclohexanol；2-methyl-1-phenylethynyl-cyclohexanol；2-Methyl-1-phenylaethinyl-cyclohexanol；2-Methyl-1-(2-phenylethynyl)cyclohexan-1-ol
• CAS: 24580-49-2
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: WDSPKJNTRYGSBV-UHFFFAOYSA-N

物化性质

• 熔点：
  87-87.5 °C(Solv: ligroine (8032-32-4))
• 沸点：
  344.2±25.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  1-(phenylethynyl)-2-methylcyclohexan-1-ol 在 甲酸 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 2-(2-methyl-1-cyclohexenyl)-1-phenylpropan-2-ol
  参考文献：
  名称：

  Efficient routes to cyclic 2,3-epoxyalcohols from cycloalkenyl ketones, via cycloalkenyl alcohols

  摘要：

  The minimising of torsional strain and non-bonding interactions is proposed as the explanation of high diastereoselectivity observed in the epoxidation of cycloalkenyl alcohols. reported for twenty three examples. The resulting 2,3-epoxyalcohols are key intermediates in the synthesis of tricyclic 1, 2-diols and beta-hydroxy ketones

  DOI：

  10.1016/s0040-4020(01)80560-3
• 作为产物：
  描述：

  2-甲基环己酮 、 苯乙炔 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 silver(I) chloride 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 水 为溶剂， 以64%的产率得到1-(phenylethynyl)-2-methylcyclohexan-1-ol
  参考文献：
  名称：

  银催化末端炔烃直接加成到水中的简单环酮

  摘要：

  首次在银催化下将末端炔烃催化加成到水中的简单环酮中。环酮与末端炔烃在水中有效反应得到相应的炔丙醇。

  DOI：

  10.1055/s-0032-1317342

文献信息

• Mild conversion of propargylic alcohols to α,β-unsaturated enones in ionic liquids (ILs); a new ‘metal free’ life for the Rupe rearrangement
  作者：Ganesh C. Nandi、Benjamin M. Rathman、Kenneth K. Laali

  DOI：10.1016/j.tetlet.2013.09.028

  日期：2013.11

  free protocol for the conversion of propargylic alcohols to cyclic and acyclic α,β-unsaturated enones via the Rupe rearrangement is reported. The method utilizes the Brønsted acidic ionic liquid [BMIM-SO3H][OTf] as catalyst and [BMIM][PF6] as solvent and offers the potential for recycling and reuse of the IL solvent. The feasibility to synthesize bicyclic fused cyclopentenone derivatives via a Rupe → Aldol → Nazarov

  报道了通过Rupe重排将炔丙醇转化为环状和无环α，β-不饱和烯酮的温和且无选择性的过渡金属方案。该方法利用布朗斯台德酸性离子液体[BMIM-SO 3 H] [OTf]作为催化剂，[BMIM] [PF 6 ]作为溶剂，为IL溶剂的再循环和再利用提供了潜力。还证明了利用该方案经由Rupe→Aldol→Nazarov序列合成双环稠合的环戊烯酮衍生物的可行性。
• Organocatalytic Alkynylation of Aldehydes and Ketones under Phase-Transfer Catalytic Conditions
  作者：Torsten Weil、Peter R. Schreiner

  DOI：10.1002/ejoc.200500064

  日期：2005.6

  We developed alkynylations of various aldehydes and ketones under practical phase-transfer conditions at room temperature. The straightforward methodology combines one-pot synthesis and simple workup with good to excellent yields for propargylic alcohols derived from aliphatic aldehydes and ketones. Even aromatic aldehydes and ketones could be transformed to the corresponding propargylic alcohols in

  我们在室温下的实际相转移条件下开发了各种醛和酮的炔基化。这种简单的方法将一锅法合成和简单的后处理与从脂肪醛和酮衍生的炔丙醇的收率良好到出色相结合。甚至芳香醛和酮也可以以略低的产率转化为相应的炔丙醇。还确定了取决于 PT 催化剂量和 NaOH 浓度的产率。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Solvent-Free Addition of Ethynylbenzene to Ketones
  作者：Hisakazu Miyamoto、Shunpei Yasaka、Koichi Tanaka

  DOI：10.1246/bcsj.74.185

  日期：2001.1

  The addition of ethynylbenzene to ketones proceeded efficiently in the absence of a solvent to give tertiary alkynols in good yields.

  在无溶剂条件下，将乙炔苯添加到酮中，能够高效地生成三取代的炔醇，且产率良好。
• SUBSTITUTED VINYL AND ALKYNYL CYANOCYCLOALKANOLS AND VINYL AND ALKYNYL CYANOHETEROCYCLOALKANOLS AS ACTIVE AGENTS AGAINST ABIOTIC PLANT STRESS
  申请人：BAYER CROPSCIENCE AKTIENGESELLSCHAFT

  公开号：US20170197910A1

  公开（公告）日：2017-07-13

  Substituted vinyl- and alkynylcyanocycloalkanols and vinyl- and alkynylcyanoheterocyclylalkanols of the general formula (I) or salts thereof where [X—Y], Q, R 1 , R 2 , A 1 , A 2 , V, W, m and n are each as defined in the description, processes for preparation thereof and the use thereof for enhancing stress tolerance in plants with respect to abiotic stress, and/or for increasing plant yield.

  通式（I）的取代乙烯基和炔基氰基环戊醇和乙烯基和炔基氰基杂环烷基醇或其盐，其中[X—Y]，Q，R1，R2，A1，A2，V，W，m和n均如描述中定义的那样，其制备方法以及用于增强植物对非生物胁迫的耐受性和/或增加植物产量的用途。
• USE OF SUBSTITUTED 1-(ARYL ETHYNYL)-, 1-(HETEROARYL ETHYNYL)-, 1-(HETEROCYCLYL ETHYNYL)- AND 1-(CYCLOALKENYL ETHYNYL)-CYCLOHEXANOLS AS ACTIVE AGENTS AGAINST ABIOTIC PLANT STRESS
  申请人：BAYER CROPSCIENCE AG

  公开号：US20150305334A1

  公开（公告）日：2015-10-29

  The invention relates to the use of substituted 1-(arylethynyl)-, 1-(heteroarylethynyl)-, 1-(heterocyclylethynyl)- and 1-(cycloalkenylethynyl)cyclohexanols or salts thereof where the radicals in the general formula (I) correspond to the definitions given in the description, for enhancing stress tolerance in plants to abiotic stress and/or for increasing plant yield.

  本发明涉及使用取代的1-(芳基乙炔基)-、1-(杂芳基乙炔基)-、1-(杂环基乙炔基)-和1-(环烯基乙炔基)环己醇或其盐，其中通式(I)中的基团与描述中给定的定义相对应，用于增强植物对非生物胁迫的耐受性和/或增加植物产量。