1-(1-phenylvinyl)cyclohexanol | 92862-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(1-phenylvinyl)cyclohexanol
• 英文别名: 1-(1-Phenylethenyl)cyclohexan-1-ol
• CAS: 92862-83-4
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: PADRSONSQDTLDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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-(1-phenylvinyl)cyclohexanol 在 potassium hydrogensulfate 作用下， 生成 1-(环己烯-1-基)乙烯基苯
  参考文献：
  名称：

  Alicyclic Syntheses. II. Diels--Alder Adducts Derived from 1-(α-Styryl)cyclohexene and 3-(α-Styryl)-▵²-cyclohexenone

  摘要：

  DOI：

  10.1021/jo01024a010
• 作为产物：
  描述：

  环己基苯基甲酮 在 三乙基铝 、 间氯过氧苯甲酸 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-(1-phenylvinyl)cyclohexanol
  参考文献：
  名称：

  AlEt3-promoted eliminative ring-opening of β-hydroxy epoxides: highly stereoselective synthesis of terminal α-hydroxy olefins

  摘要：

  AlEt3-promoted eliminative ring-opening of beta-epoxy alcohols leading to alpha-hydroxy olefins is reported. This eliminative ring-opening reaction is shown to be highly stereoselective, thus providing an alternative asymmetric synthesis for a-hydroxy olefins. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00457-9

文献信息

• Synthesis of Functionalized Epoxides by Copper-Catalyzed Alkylative Epoxidation of Allylic Alcohols with Alkyl Nitriles
  作者：Ala Bunescu、Qian Wang、Jieping Zhu

  DOI：10.1021/acs.orglett.5b00571

  日期：2015.4.17

  A copper-catalyzed oxyalkylation of allylic alcohols using nonactivated alkyl nitriles as reaction partners was developed. A sequence involving generation of an alkyl nitrile radical followed by its addition to a double bond and a copper-mediated formation of C(sp3)–O bond was proposed to account for the reaction outcome. The protocol provided an efficient route to functionalized tri- and tetrasubstituted

  开发了使用未活化的烷基腈作为反应伙伴的铜催化的烯丙醇的烷氧基化反应。为了说明反应的结果，提出了一个序列，该序列涉及生成烷基腈自由基，然后将其添加至双键和铜介导的C（sp 3）-O键形成。该协议通过形成具有中等至极好非对映选择性的C（sp 3）–C（sp 3）和C（sp 3）–O键，为官能化的三取代和四取代的环氧化物提供了一条有效途径。
• A catalytic allylic cation-induced intermolecular allylation-semipinacol rearrangement
  作者：Ming-Hui Xu、Kun-Long Dai、Yong-Qiang Tu、Xiao-Ming Zhang、Fu-Min Zhang、Shao-Hua Wang

  DOI：10.1039/c8cc04285c

  日期：——

  A catalytic intermolecular semipinacol rearrangement induced by allylic carbocations has been realized. This tandem reaction is highly efficient under the catalysis of ZnBr2, generating a wide range of α-homoallyl substituted ketones which contain all-carbon quaternary centres in good to excellent yields (up to 98%) with moderate to high diastereoselectivities (up to >20 : 1). Synthetic application

  已经实现了烯丙基碳正离子诱导的催化分子间半频哪醇重排。该串联反应在ZnBr 2的催化下非常高效，生成了多种α-均烯丙基取代的酮，其中含有全碳季中心，收率高至极好（高达98％），具有中等到高的非对映选择性（高达> 20：1）。还报道了这种新方法在天然产物核心结构构建中的合成应用。
• Selective Aerobic Oxygenation of Tertiary Allylic Alcohols with Molecular Oxygen
  作者：Bencong Zhu、Tao Shen、Xiaoqiang Huang、Yuchao Zhu、Song Song、Ning Jiao

  DOI：10.1002/anie.201903690

  日期：2019.8.5

  Aerobic epoxidation of tertiary allylic alcohols remains a significant challenge. Reported here is an efficient and highly chemoselective copper‐catalyzed epoxidation and semipinacol rearrangement reaction of tertiary allylic alcohols with molecular oxygen. The solvent 1,4‐dioxane activates dioxygen, thereby precluding the addition of a sacrificial reductant.

  叔烯丙醇的有氧环氧化仍然是一个重大挑战。此处报道了叔烯丙基醇与分子氧的高效且高度化学选择性的铜催化的环氧化和半频哪醇重排反应。溶剂1,4-二恶烷会激活双氧，从而排除了牺牲性还原剂的添加。
• Synthesis of Macrocyclic Ketones through Catalyst-Free Electrophilic Halogen-Mediated Semipinacol Rearrangement: Application to the Total Synthesis of (±)-Muscone
  作者：Yi Liu、Ying-Yeung Yeung

  DOI：10.1021/acs.orglett.7b00350

  日期：2017.3.17

  The rearranged products could further undergo Dowd–Beckwith rearrangement to give the corresponding one-carbon ring-expanded ketones. This approach has been applied to the total synthesis of the natural product (±)-muscone, which is widely used in modern perfumery and medicines, in a two-step sequence.

  在温和条件下，使用亲电卤素介导的频哪醇重排成功制备了一系列大环化合物。尽管从小环到中环的膨胀在能量上是不利的过程，但发现亲电子卤化的能力足以克服这种能垒。重排的产物可进一步进行Dowd-Beck的重排，得到相应的一碳环扩酮。该方法已应用于两步序列的天然产物（±）-麝香酮的全合成，这种物质在现代香料和药物中被广泛使用。
• Regioselective radical cyclization initiated by the reaction of allylic hydroperoxides with iron(II) sulfate
  作者：Araki Masuyama、Tomohiro Sugawara、Masatomo Nojima、Kevin J McCullough

  DOI：10.1016/s0040-4020(02)01522-3

  日期：2003.1

  FeSO4/CuCl2 yielded 1-(1-chlorocyclohexyl)ethanone as the major product consistent with 6-endo-trig cyclization of the intermediate 5-acetylhex-5-enyl radical. This strategy was extended to the ring enlargement of a series of 1-isopropenylcycloalkyl hydroperoxides. Regioselective 7- or 8-endo-trig cyclization reactions could be achieved by treatment of the corresponding cyclopentyl or cyclohexyl hydroperoxides

  与硫酸亚铁的混合物1-甲基-2-亚甲基-1-环己基氢过氧化物的治疗4 /的CuCl 2，得到1-（1-氯环）乙酮，与6-一致主要产物内切- trig的中间体5- acetylhex的环化-5-烯基。该策略扩展到一系列1-异丙烯基环烷基氢过氧化物的扩环。区域选择性7-或8-内切- trig的环化反应可通过处理相应的环戊基或环己基氢过氧化物的用任一个的FeSO的混合物来实现4 /的CuCl 2或的FeSO 4只。取代基对8-效率的影响远藤- trig的环化过程中还探讨。