6-phenyl-hex-3-en-1-ol | 64025-65-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-phenyl-hex-3-en-1-ol
• 英文别名: 6-Phenylhex-3-en-1-ol
• CAS: 64025-65-6
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: IPXDXYADIJHFOR-UHFFFAOYSA-N

物化性质

• 沸点：
  300.8±21.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  6-phenyl-hex-3-en-1-ol 在 亚碘酰苯 、 silver trifluoromethanesulfonate 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  通过调节金属：配体比率实现催化剂控制的硝基转移：深入了解化学选择性的机理

  摘要：

  Catalyst.controlled, selective nitrene transfer is often challenging when both C-H and C=C bonds are present in a substrate. Interestingly, a simple change in the Ag(I):L ratio (L = bidentate N,N-donor ligand) enables tunable, chemoselective nitrene transfer that favors either C= C bond aziridination using an similar to 1:1 Ag:L ratio (AgLOTf) or insertion into a C-H bond when the Ag:L ratio in the catalyst is 1:2 (AgL2OTO. In this paper, mechanistic studies, coupled with kinetic profiling of the entire reaction course, are employed to examine the reasons for this unusual behavior. Steady-state kinetics were found to be similar for both AgLOTf and AgL2OTf; both complexes yield electronically similar reactive intermediates that engage in nitrene transfer involving formation of a short-lived radical intermediate and barrierless radical recombination. Taken together,, experimental and computational studies point to two effects that control tunable: cherrioSelectiVity: suppression of aziridination as the steric congestion around the silver center is increased in AgL2OTf and a decrease in the rate of C-H insertion with AgLOTf in comparison to AgL2OTE The observation that the sterics of Ag catalysts can be varied, with minor effects on the electronic features of the putative nitrene, has important implications for the development of other silver catalysts that enable tunable, site-selective C-H bond aminations..

  DOI：

  10.1021/acs.organomet.7b00190
• 作为产物：
  描述：

  4-苯基丁醛 在 哌啶 、 lithium aluminium tetrahydride 、 硫酸 、 溶剂黄146 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 14.67h， 生成 6-phenyl-hex-3-en-1-ol
  参考文献：
  名称：

  邻近基团协助催化脂肪族内部烯烃的区域和对映选择性氧三氟甲基硫醇化

  摘要：

  公开了通过形式上的分子间策略手性硒化物催化的脂肪族内烯烃的氧三氟甲基硫醇化，提供了具有高区域，对映体和非对映选择性的CF 3 S 1,3-氨基醇和1,3-二醇衍生物。底物上相邻的酰亚胺或酯基团通过六元环过渡态促进了反应。该辅助策略也成功地应用于内部烯烃的区域和非对映选择性的氧卤官能化以及炔烃的转化。

  DOI：

  10.1021/acs.orglett.8b02672

文献信息

• Iridium-Catalyzed Regioselective Hydroalkynylation of Internal Alkenes Directed by an Oxime
  作者：Peng-Chao Gao、Zi-Xuan Wang、Bi-Jie Li

  DOI：10.1021/acs.orglett.1c03707

  日期：2021.12.17

  hydroalkynylation of allylic alcohols protected by an oxime group. Catalytic alkynylation occurs exclusively at the distal position of the alkene. This method generates γ-alkynyl alcohol oximes directly from internal alkenes and terminal alkynes. The oxime group can be readily removed to afford a free alcohol, thus providing an indirect route for the catalytic hydroalkynylation of allylic alcohols.

  我们在这里报告了由肟基团保护的烯丙醇的铱催化氢化炔基化。催化炔基化仅发生在烯烃的远端位置。该方法直接从内部烯烃和末端炔烃生成 γ-炔醇肟。肟基可以很容易地去除以提供游离醇，从而为烯丙醇的催化加氢炔基化提供间接途径。
• Chiral Selenide-Catalyzed Enantioselective Construction of Saturated Trifluoromethylthiolated Azaheterocycles
  作者：Jie Luo、Yannan Liu、Xiaodan Zhao

  DOI：10.1021/acs.orglett.7b01392

  日期：2017.7.7

  An indane-based, bifunctional, chiral selenide catalyst has been developed. The new catalyst is efficient for the enantioselective synthesis of saturated azaheterocycles possessing a trifluoromethylthio group. The desired products were obtained in good yields with high diastereo- and enantioselectivities.

  已经开发出基于茚满的，双官能的手性硒化物催化剂。该新型催化剂对于具有三氟甲硫基的饱和氮杂杂环的对映选择性合成是有效的。以高产率得到具有高非对映选择性和对映选择性的所需产物。
• Bis-Boric Acid-Mediated Regioselective Reductive Aminolysis of 3,4-Epoxy Alcohols
  作者：Wei Tang、Chuan Wang

  DOI：10.1021/acs.joc.2c01878

  日期：2022.11.18

  Herein we report a bis-boric acid-mediated regioselective reductive aminolysis of 3,4-epoxy alcohols, providing new access to prepare amino diols in high diastereofidelity directly starting from nitroarenes. Notably, this step-economical process is enabled by the essential dual function of bis-boric acid, which is engaged initially in the 4,4′-bipyridine-catalyzed reduction of nitro compounds as the

  在此，我们报告了双硼酸介导的 3,4-环氧醇的区域选择性还原氨解，为直接从硝基芳烃制备高非对映保真度的氨基二醇提供了新途径。值得注意的是，这一步骤经济的过程是由双硼酸的基本双重功能实现的，双硼酸最初作为还原剂参与硝基化合物的 4,4'-联吡啶催化还原，随后促进 3 的开环反应,4-环氧醇与原位生成的苯胺。
• Oxygen-Directed Intramolecular Hydroboration
  作者：Robert-André F. Rarig、Matthew Scheideman、Edwin Vedejs

  DOI：10.1021/ja800402g

  日期：2008.7.1

  Metal-free homoallylic oxygen-directed intramolecular hydroboration is reported. Regioselectivities from 20:1 to 82:1 favoring the 1,3-dioxy-substituted products have been achieved using Me2S center dot BH3/TfOH followed by standard oxidative workup. Branching at the C5 position improves regioselectivity.
• 256. Reduced cyclic compounds. Part I. The preparation and cyclodehydration of ω-phenyl unsaturated tertiary alcohols
  作者：M. F. Ansell、M. E. Selleck

  DOI：10.1039/jr9560001238

  日期：——