9-t-butyldiphenylsilyloxy-1-nonanol | 139258-85-8

• 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: 9-t-butyldiphenylsilyloxy-1-nonanol
• 英文别名: 9-(tert-butyldiphenylsilyloxy)-nonan-1-ol；9-(tert-butyldiphenylsilyloxy)nonanol；9-[Tert-butyl(diphenyl)silyl]oxynonan-1-ol
• CAS: 139258-85-8
• 化学式: C₂₅H₃₈O₂Si
• 分子量: 398.661
• InChiKey: BZCOUVKFGGKHLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  463.7±27.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-t-butyldiphenylsilyloxy-1-nonanol 在 吡啶 、 四丁基氟化铵 、 sodium acetate 、 magnesium 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 76.0h， 生成 癸醛,9-(苯甲酰氧基)-
  参考文献：
  名称：

  Floc'h, Y. Le; Yvergnaux, F.; Toupet, L., Bulletin de la Societe Chimique de France, 1991, # 5, p. 742 - 759

  摘要：

  DOI：
• 作为产物：
  描述：

  1,9-壬二醇 在 咪唑 、 水 、 sodium hydride 、 氢化铝 作用下， 以 正己烷 为溶剂， 反应 14.0h， 生成 9-t-butyldiphenylsilyloxy-1-nonanol
  参考文献：
  名称：

  Utilization of neutral alumina as a mild reagent for the selective cleavage of primary and secondary silyl ethers

  摘要：

  The selective cleavage of primary and secondary trimethylsilyl (TMS), triisopropylsilyl (TIPS), tert-butyldimethylsilyl (TBDMS) and tert-butyldiphenylsilyl (TBDPS) ethers with neutral alumina under very mild conditions is described. The method involves utilization of the support, previously activated by heating at 80 degrees C/0.1 torr for 16 h and later deactivated with variable amounts of water (1.5-4.5%), in 50:1 ratio with regard to the substrate and in the presence of non-polar solvents, like hexane. The deprotection rate depends on the steric bulkiness of the silicon substituents, following the order TMS > > TBDMS approximate to TIPS > TBDPS, as well as on the type of the attached carbon. The procedure can discriminate between different silyl groups located at equivalent positions of the same molecule affording the corresponding monoprotected alcohols in very good yields.

  DOI：

  10.1016/s0040-4020(01)85572-1

文献信息

• A convenient biphasic process for the monosilylation of symmetrical 1,n-primary diols
  作者：Chengzhi Yu、Bin Liu、Longqin Hu

  DOI：10.1016/s0040-4039(00)00626-2

  日期：2000.6

  A simple and mild biphasic process was developed for the selective protection of one of two chemically equivalent primary hydroxyl groups in 1,n-diols using t-butyldiphenyl silyl chloride in diisopropyl ethyl amine and dimethyl formamide.

  开发了一种简单温和的两相过程，用于在二异丙基乙胺和二甲基甲酰胺中使用叔丁基二苯基甲硅烷基氯选择性保护1，n-二醇中两个化学等效的伯羟基之一。
• Molecular Design, Synthesis, and Evaluation of Novel Potent Apoptosis Inhibitors Inspired from Bongkrekic Acid
  作者：Katsuhiro Okuda、Keisuke Hasui、Masato Abe、Kenji Matsumoto、Mitsuru Shindo

  DOI：10.1021/tx300315h

  日期：2012.10.15

  were then evaluated. All tested tricarboxylic acid derivatives including BKA showed little toxicity against HeLa cells. BKA and two of the synthesized derivatives significantly suppressed staurosporine (STS)-induced reductions in cell viability. Furthermore, STS-induced ΔΨm collapse was significantly restored by pretreatment with BKA and a tricarboxylic acid derivative. Other derivatives, in which

  邦克里克酸（BKA）是腺嘌呤核苷酸转位酶（ANT）的抑制剂。由于ANT的抑制与细胞色素c的抑制有关从线粒体释放，然后导致细胞凋亡的抑制，它已被用作细胞凋亡机制研究的工具。BKA由具有两个不对称中心的长碳链，一个非共轭烯烃，两个共轭二烯，三个甲基，一个甲氧基和三个羧酸组成。这种复杂的化学结构在合成，供应和生化机理研究中造成了困难。在这项研究中，我们设计并合成了更多受BKA分子结构启发的简单三羧酸。然后评估了它们在HeLa细胞中的细胞毒性和防止凋亡活性以及对HL-60细胞中线粒体内膜电位（ΔΨm）的影响。所有测试的三羧酸衍生物（包括BKA）对HeLa细胞的毒性均很小。BKA和两个合成的衍生物显着抑制星形孢菌素（STS）诱导的细胞活力降低。此外，通过用BKA和三羧酸衍生物预处理，STS诱导的ΔΨm塌陷得以显着恢复。其中三种羧酸之一被酯化的其他衍生物表现出强毒性，尤其是带有与BKA相同长度的碳链的
• Development of Hybrid Phospholipid Mimics as Effective Agonists for Liver Receptor Homologue-1
  作者：Autumn R. Flynn、Suzanne G. Mays、Eric A. Ortlund、Nathan T. Jui

  DOI：10.1021/acsmedchemlett.8b00361

  日期：2018.10.11

  for metabolic disorders. The most effective known LRH-1 modulators are phospholipids or synthetic hexahydropentalene compounds. While both classes have micromolar efficacy, they target different portions of the ligand binding pocket and activate LRH-1 through different mechanisms. Guided by crystallographic data, we combined aspects of both ligand classes into a single scaffold, resulting in the most

  孤儿核受体肝受体Homologue-1（LRH-1）是代谢疾病的新兴药物靶标。已知最有效的LRH-1调节剂是磷脂或合成的六氢戊烯化合物。虽然这两种类型都具有微摩尔功效，但它们靶向配体结合口袋的不同部分并通过不同机制激活LRH-1。根据晶体学数据，我们将两种配体类型的各个方面组合到一个支架中，从而产生了迄今为止最有效，最有效的LRH-1激动剂。
• Synthesis of the Esterified Cerebroside in the Epidermis of Guinea Pigs
  作者：Hiroyuki Nishio、Kenji Mori

  DOI：10.1271/bbb.59.1644

  日期：1995.1

  (2S,3R,4E,23’Z)-1-O-(β-D-Glucopyranosyl)-N-(32’-linoleoyloxy-23’-dotriacontenoyl)-4-sphingenine (1), a component of the esterified cerebrosides in the epidermis of guinea pigs, was synthesized by selective N-acylation of (2S,3R,4E)-1-O-(β-D-glucopyranosyl)-4-sphingenine (18) with activated ω-linoleoyloxy fatty acid ester 17.

  (2S,3R,4E,23’Z)-1-O-(β-D-葡萄糖吡喃糖基)-N-(32’-亚油酸氧基-23’-二十二烷基)-4-神经酰胺（1）是豚鼠表皮中酯化脑苷脂的成分，通过选择性N-酰化反应合成了(2S,3R,4E)-1-O-(β-D-葡萄糖吡喃糖基)-4-神经酰胺（18）与活化的ω-亚油酸氧基脂肪酸酯17。
• Method of treating dry eye disorders using 13(S)-HODE and its analogs
  申请人：Klimko G. Peter

  公开号：US20060128803A1

  公开（公告）日：2006-06-15

  The topical use of 13(S)-HODE and analogs are disclosed for the treatment of dry eye disorders.

  本发明揭示了用于治疗干眼症的13(S)-HODE和类似物的局部应用。