8-bromo-1-(tert-butyldiphenylsilyloxy)-octane | 172995-43-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 8-bromo-1-(tert-butyldiphenylsilyloxy)-octane
• 英文别名: 8-bromo-1-O-(tert-butyldiphenylsilyl)octanol；1-bromo-8-(tert-butyldiphenylsilyloxy)-octane；8-tert-butyldiphenylsilyloxyoctyl-1-bromide；8-Bromooctoxy-tert-butyl-diphenylsilane
• CAS: 172995-43-6
• 化学式: C₂₄H₃₅BrOSi
• 分子量: 447.531
• InChiKey: DKKLGOGRQGKVSV-UHFFFAOYSA-N

物化性质

• 沸点：
  461.5±37.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  8-bromo-1-(tert-butyldiphenylsilyloxy)-octane 在 sodium periodate 、 四氧化锇 、 magnesium 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 生成
  参考文献：
  名称：

  [EN] NOVEL DIESTER AND TRIESTER BASED LOW MOLECULAR WEIGHT, BIODEGRADABLE CATIONIC LIPIDS FOR OLIGONUCLEOTIDE DELIVERY
  [FR] NOUVEAUX LIPIDES CATIONIQUES BIODÉGRADABLES DE FAIBLE MASSE MOLÉCULAIRE À BASE DE DIESTER ET TRIESTER POUR LA DÉLIVRANCE D'OLIGONUCLÉOTIDES

  摘要：

  本发明提供了一种新型的阳离子脂质A公式，可以与胆固醇和PEG脂质等其他脂质成分结合使用，形成含寡核苷酸的脂质纳米粒子。本发明的目的是提供一种阳离子脂质支架，其具有增强的功效，同时由于肝脏中脂质水平降低而具有较低的肝毒性。本发明采用低分子量阳离子脂质，其中一个短脂链与脂链中的可水解功能包括，以增强siRNA在体内传递的效率和耐受性。

  公开号：

  WO2013158579A1
• 作为产物：
  描述：

  1,8-辛二醇 在 咪唑 、 氢溴酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 8-bromo-1-(tert-butyldiphenylsilyloxy)-octane
  参考文献：
  名称：

  Total synthesis of cytotoxic sponge alkaloids hachijodines F and G

  摘要：

  The total synthesis of two cytotoxic sponge alkaloids haehijodines F (1) and G (2) via a common intermediate 3 is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00379-9

文献信息

• Stannyl Radical-Mediated Cleavage of π-Deficient Heterocyclic Sulfones. Synthesis of α-Fluoro Esters
  作者：Stanislaw F. Wnuk、Jeannette M. Rios、Jahanzeb Khan、Ya-Li Hsu

  DOI：10.1021/jo000342n

  日期：2000.6.1

  1 h under these conditions. This represents a mild new methodology for removal of the synthetically useful sulfone moiety. Substitution of Bu(3)SnD for Bu(3)SnH gave access to alpha-deuterium-labeled esters. Treatment of the alpha-(pyrimidin-2-ylsulfonyl) enolates derived from several esters with Selectfluor gave high yields of the 2-fluoro-2-(pyrimidin-2-ylsulfonyl)alkanoates, which were smoothly

  用三丁基锡烷和偶氮双（2-甲基-2-丙腈）（AIBN）在苯中回流处理2-（吡啶-2-基磺酰基）己酸乙酯36小时，导致氢解生成己酸乙酯（60％），而没有回流48小时后，观察到与2-（苯磺酰基）己酸乙酯反应。在这些条件下，在1小时内对2-（嘧啶-2-基磺酰基）己酸乙酯进行定量氢解。这代表了去除合成上有用的砜部分的温和的新方法。用Bu（3）SnD代替Bu（3）SnH可以访问α-氘标记的酯。用Selectfluor处理衍生自几种酯的α-（嘧啶-2-基磺酰基）烯醇酸酯，可高产率地生产2-氟-2-（嘧啶-2-基磺酰基）链烷酸酯，将其平滑地进行磺酰化[Bu（3）SnH（2当量）/ AIBN /苯/δ]，得到2-氟链烷酸酯。在氟化钾的存在下，由氯化三苯甲基氯化锡（0.15当量）和过量的聚甲基氢硅氧烷生成的“催化”氢化锡，还以高收率实现了从酸衍生物中去除pi不足的α-（嘧啶-2-基磺酰基）部分。建议通过烷氧基酮基型自由基和烯醇锡进行脱磺酰化。
• Structure Determination of an Endogenous Sleep-Inducing Lipid, <i>cis</i>-9-Octadecenamide (Oleamide):  A Synthetic Approach to the Chemical Analysis of Trace Quantities of a Natural Product
  作者：Benjamin F. Cravatt、Richard A. Lerner、Dale L. Boger

  DOI：10.1021/ja9532345

  日期：1996.1.1

  The pursuit of endogenous sleep-inducing substances has been the focus of an extensive, complicated body of research. Several compounds, including Delta-sleep-inducing peptide and prostaglandin D-2, have been suggested to play a role in sleep induction, and yet, the molecular mechanisms of this physiological process remain largely unknown. In recent efforts, the cerebrospinal fluid of deep-deprived cats was analyzed in search of compounds that accumulated during sleep deprivation. An agent with the chemical formula C18H35NO was found to cycle with sleep-wake patterns, increasing in concentration with sleep deprivation and decreasing in amount upon recovery sleep. Since the material was generated in minute quantities and only under the special conditions of sleep deprivation, efforts to isolate sufficient material for adequate characterization, structure identification, and subsequent detailed evaluation of its properties proved unrealistic. With the trace amounts of the impure endogenous compound available, extensive MS studies on the agent were completed, revealing key structural features of the molecule including two degrees of unsaturation, a long alkyl chain, and a nitrogen substituent capable of fragmenting as ammonia. Additionally, HPLC traces suggested a weak UV absorbance for the unknown material. With this data in hand and encouraged by the relatively small size of the molecule, MW = 281, a synthetic approach toward the structural identification of the natural compound was initiated. Herein, we report the full details of the synthesis and comparative characterization of candidate structures for this endogenous agent that led to the unambiguous structural correlation with synthetic cis-9-octadecenamide.
• Synthesis and biological properties of tensyuic acids B, C, and E, and investigation of the optical purity of natural tensyuic acid B
  作者：Takanori Matsumaru、Toshiaki Sunazuka、Tomoyasu Hirose、Aki Ishiyama、Miyuki Namatame、Takashi Fukuda、Hiroshi Tomoda、Kazuhiko Otoguro、Satoshi Ōmura

  DOI：10.1016/j.tet.2008.05.035

  日期：2008.7

  The first, concise total synthesis of (+/-)-tensyuic acids B, C, and E, using chemoselective formal S(N)2' type Grignard reactions and selective esterification, is described. In addition, the optical purity of natural (+/-)tensyuic acid B was determined using Chirabite-AR. Synthetic tensyuic acids, together with their intermediate compounds, were found to possess useful bioactive properties, with some of them showing potent activity against Trypanosorna brucei brucei strain GUTat 3.1. (c) 2008 Elsevier Ltd. All rights reserved.
• EP807626
  申请人：——

  公开号：——

  公开（公告）日：——
• Total synthesis of cytotoxic sponge alkaloids hachijodines F and G
  作者：William R.F. Goundry、Victor Lee、Jack E. Baldwin

  DOI：10.1016/s0040-4039(02)00379-9

  日期：2002.4

  The total synthesis of two cytotoxic sponge alkaloids haehijodines F (1) and G (2) via a common intermediate 3 is described. (C) 2002 Elsevier Science Ltd. All rights reserved.