6-(trityloxy)hex-1-en | 185999-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 6-(trityloxy)hex-1-en
• 英文别名: ((hex-5-en-1-yloxy)methanetriyl)tribenzene；[Hex-5-enoxy(diphenyl)methyl]benzene
• CAS: 185999-03-5
• 化学式: C₂₅H₂₆O
• 分子量: 342.481
• InChiKey: AEUJEGCXJIQVKY-UHFFFAOYSA-N

物化性质

• 沸点：
  447.7±24.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(trityloxy)hex-1-en 在 2,6-二甲基吡啶 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (2R)-1-(4-methoxyphenoxy)-6-trityloxyhexan-2-ol
  参考文献：
  名称：

  Single Enantiomer Epoxides by Bromomandelation of Prochiral Alkenes

  摘要：

  A combination of mandelic acid and N-bromosuccinimide efficiently converts prochiral alkenes into a readily separable 1:1 mixture of the bromomandelates. The diastereomerically pure bromomandelates are then converted into a variety of enantiomerically pure products. Terminal alkenes are converted into enantiomerically pure epoxides. Cyclohexene is converted into enantiomerically pure cis-2-azidocyclohexanol and cis-2-phenylthiocyclohexanol.

  DOI：

  10.1021/jo061818r
• 作为产物：
  描述：

  [Diphenyl(6-phenylmethoxyhexoxy)methyl]benzene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到6-(trityloxy)hex-1-en
  参考文献：
  名称：

  A Simple Method for the Conversion of Primary Alcohols into Terminal Olefins

  摘要：

  对初级醇的苄基醚进行n-丁基锂（n-BuLi）处理，获得了良好产率的末端烯烃。

  DOI：

  10.1246/cl.1996.1039

文献信息

• Room Temperature Ambient Pressure (RTAP)-Hydroformylation in Water Using a Self-Assembling Ligand
  作者：Alexander T. Straub、Marina Otto、Ippei Usui、Bernhard Breit

  DOI：10.1002/adsc.201300258

  日期：2013.7.8

  We herein demonstrate a hydroformylation at room temperature and ambient pressure (RTAP) using our Rh/6‐DPPon (1) system in aqueous media. The hydrogen bonding network of the ligand backbone stays intact, exemplified by the excellent regioselectivity for the linear aldehyde. Various substrates with different functional groups (with some prone to hydrolysis) are stable under the applied conditions and

  我们在本文中证明了使用我们的Rh / 6-DPPon（1）系统在水性介质中在室温和环境压力（RTAP）下进行加氢甲酰化。配体主链的氢键网络保持完整，例如对线性醛具有出色的区域选择性。具有不同官能团（容易水解）的各种底物在所施加的条件下是稳定的，并且可以进行加氢甲酰化，从而获得良好的收率。
• Photocatalytic Cleavage of Trityl Protected Thiols and Alcohols
  作者：Sho Murakami、Cosima Brudy、Bartholomäus Pieber、Moritz Bachmann、Yoshiji Takemoto

  DOI：10.1055/a-1979-5933

  日期：——

  We report the visible light photocatalytic cleavage of trityl thioethers or ethers under pH-neutral conditions. The method results in the formation of the respective symmetrical disulfides and alcohols in moderate to excellent yield. The protocol only requires the addition of a suitable photocatalyst and light rendering it orthogonal to several functionalities, including acid labile protective groups

  我们报告了在 pH 中性条件下三苯甲基硫醚或醚的可见光光催化裂解。该方法导致以中等到极好的收率形成相应的对称二硫化物和醇。该协议只需要添加合适的光催化剂和光使其与多种功能正交，包括酸不稳定保护基团。相同的条件可用于直接将三苯甲基保护的硫醇转化为不对称的二硫化物或硒硫化物，并在固相有机合成中裂解三苯甲基树脂。
• Synthesis of diether-linked cationic lipids for gene delivery
  作者：Tan Ren、Dexi Liu

  DOI：10.1016/s0960-894x(99)00187-0

  日期：1999.5

  Quaternary ammonium lipids 1b-d, with diether linkages between hydrocarbon chains and butane or hexane backbone, were synthesized for cationic liposome-mediated gene delivery. The synthetic strategy of using C-4 or C-6 synthon permits the achievement of the variation of the hydrophobic domain as well as changes of space between the quaternary ammonium head and the hydrophobic domain in the diether-linked cationic lipids. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Marine Natural Product Honaucin A Attenuates Inflammation by Activating the Nrf2-ARE Pathway
  作者：Samantha J. Mascuch、Paul D. Boudreau、Tristan M. Carland、N. Tessa Pierce、Joshua Olson、Mary E. Hensler、Hyukjae Choi、Joseph Campanale、Amro Hamdoun、Victor Nizet、William H. Gerwick、Teresa Gaasterland、Lena Gerwick

  DOI：10.1021/acs.jnatprod.7b00734

  日期：2018.3.23

  The cyanobacterial marine natural product honaucin A inhibits mammalian innate inflammation in vitro and in vivo. To decipher its mechanism of action, RNA sequencing was used to evaluate differences in gene expression of cultured macrophages following honaucin A treatment. This analysis led to the hypothesis that honaucin A exerts its anti-inflammatory activity through activation of the cytoprotective nuclear erythroid 2-related factor 2 (Nrf2)-antioxidant response element/electrophile response element (ARE/EpRE) signaling pathway. Activation of this pathway by honaucin A in cultured human MCF7 cells was confirmed using an Nrf2 luciferase reporter assay. In vitro alkylation experiments with the natural product and N-acetyl-L-cysteine suggest that honaucin A activates this pathway through covalent interaction with the sulfhydryl residues of the cytosolic repressor protein Keapl. Honaucin A presents a potential therapeutic lead for diseases with an inflammatory component modulated by Nrf2-ARE.