1,7,7-Trimethyl-2-trimethylsilyloxybicyclo[2.2.1]heptane-2-carbonitrile | 50361-52-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,7,7-Trimethyl-2-trimethylsilyloxybicyclo[2.2.1]heptane-2-carbonitrile
• 英文别名: 1,7,7-trimethyl-2-trimethylsilyloxybicyclo[2.2.1]heptane-2-carbonitrile
• CAS: 50361-52-9
• 化学式: C₁₄H₂₅NOSi
• 分子量: 251.444
• InChiKey: ZYXLSWOSEYNVLC-UHFFFAOYSA-N

物化性质

• 沸点：
  287.7±23.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,7,7-Trimethyl-2-trimethylsilyloxybicyclo[2.2.1]heptane-2-carbonitrile 在 air 、 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.25h， 生成 homocamphoric acid anhydride
  参考文献：
  名称：

  McIntosh, John M.; Cassidy, Kenneth C., Canadian Journal of Chemistry, 1991, vol. 69, # 8, p. 1315 - 1319

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基氰硅烷 、 樟脑 在 三(2,4,6-三甲氧基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以76%的产率得到1,7,7-Trimethyl-2-trimethylsilyloxybicyclo[2.2.1]heptane-2-carbonitrile
  参考文献：
  名称：

  Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP): Efficient Catalysts for the Cyanosilylation and Cyanocarbonation of Aldehydes and Ketones

  摘要：

  多种醛和酮在1-5摩尔%的三(2,4,6-三甲氧基苯基)膦(TTMPP)存在下，良好至优秀产率地转化为相应的氰醇硅醚。同时，使用5-10摩尔%的TTMPP作为有机催化剂，氰醇碳酸酯也可以快速制备。

  DOI：

  10.3390/molecules14093353

文献信息

• Mechanism-Based Inactivation of Human Cytochrome P450 3A4 by Two Piperazine-Containing Compounds
  作者：Amanda K. Bolles、Rina Fujiwara、Erran D. Briggs、Amin A. Nomeir、Laura Lowe Furge

  DOI：10.1124/dmd.114.060459

  日期：2014.12

  Human cytochrome P450 3A4 (CYP3A4) is responsible for the metabolism of more than half of pharmaceutic drugs, and inactivation of CYP3A4 can lead to adverse drug-drug interactions. The substituted imidazole compounds 5-fluoro-2-[4-[(2-phenyl-1 H -imidazol-5-yl)methyl]-1-piperazinyl]pyrimidine (SCH 66712) and 1-[(2-ethyl-4-methyl-1 H -imidazol-5-yl)methyl]-4-[4-(trifluoromethyl)-2-pyridinyl]piperazine (EMTPP) have been previously identified as mechanism-based inactivators (MBI) of CYP2D6. The present study shows that both SCH 66712 and EMTPP are also MBIs of CYP3A4. Inhibition of CYP3A4 by SCH 66712 and EMTPP was determined to be concentration, time, and NADPH dependent. In addition, inactivation of CYP3A4 by SCH 66712 was shown to be unaffected by the presence of electrophile scavengers. SCH 66712 displays type I binding to CYP3A4 with a spectral binding constant ( K s) of 42.9 ± 2.9 µ M. The partition ratios for SCH 66712 and EMTPP were 11 and 94, respectively. Whole protein mass spectrum analysis revealed 1:1 binding stoichiometry of SCH 66712 and EMTPP to CYP3A4 and a mass increase consistent with adduction by the inactivators without addition of oxygen. Heme adduction was not apparent. Multiple mono-oxygenation products with each inactivator were observed; no other products were apparent. These are the first MBIs to be shown to be potent inactivators of both CYP2D6 and CYP3A4.

  人细胞色素P450 3A4（CYP3A4）负责代谢超过一半的药物，CYP3A4的失活可能导致不良的药物-药物相互作用。先前已鉴定出取代咪唑化合物5-氟-2-[4-[(2-苯基-1H-咪唑-5-基)甲基]-1-哌嗪基]嘧啶（SCH 66712）和1-[(2-乙基-4-甲基-1H-咪唑-5-基)甲基]-4-[4-(三氟甲基)-2-吡啶基]哌嗪（EMTPP）为CYP2D6的基于机制的失活剂（MBI）。本研究显示，SCH 66712和EMTPP同样是CYP3A4的MBI。SCH 66712和EMTPP对CYP3A4的抑制作用被确定为浓度、时间和NADPH依赖性的。此外，SCH 66712对CYP3A4的失活作用在存在亲电子清除剂的情况下不受影响。SCH 66712显示出I型结合到CYP3A4，光谱结合常数（Ks）为42.9 ± 2.9 µM。SCH 66712和EMTPP的分区比分别为11和94。全蛋白质质谱分析揭示了SCH 66712和EMTPP与CYP3A4的1:1结合化学计量比，以及与失活剂结合的质量增加，且没有氧的添加。血红素加合物不明显。观察到每个失活剂的多个单氧化产物；没有其他产物明显。这些是首次被证明对CYP2D6和CYP3A4都有强失活作用的MBI。
• Dodecatungestophosphoric acid (H3PW12O40) as a solid green BrØnsted acid catalyzes high yielding and efficient trimethylcyanosylilation reactions of aldehydes and ketones by trimethylsilyl cyanide
  作者：Habib Firouzabadi、Nasser Iranpoor、Abbas Ali Jafari

  DOI：10.1016/j.jorganchem.2004.12.025

  日期：2005.3

  An efficient solvent-free method is described for the addition of TMSCN to carbonyl groups employing dodecatungestophosphoric acid (H3PW12O40) as a heterogeneous and environmentally benign catalyst. By this method, aromatic, aliphatic, cyclic and heterocyclic aldehydes and ketones are converted into their corresponding cyanotrimethylsilyl ethers in excellent yields (89-98%) in short reaction times (< 10 min). (c) 2004 Published by Elsevier B.V.
• Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP): Efficient Catalysts for the Cyanosilylation and Cyanocarbonation of Aldehydes and Ketones
  作者：Satoru Matsukawa、Izumi Sekine、Ayumi Iitsuka

  DOI：10.3390/molecules14093353

  日期：——

  A variety of aldehydes and ketones were transformed to their corresponding cyanohydrin silyl ethers in good to excellent yields in the presence of 1-5 mol% of tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP). Cyanohydrin carbonates were also readily prepared using 5-10 mol% of TTMPP as an organocatalyst.

  多种醛和酮在1-5摩尔%的三(2,4,6-三甲氧基苯基)膦(TTMPP)存在下，良好至优秀产率地转化为相应的氰醇硅醚。同时，使用5-10摩尔%的TTMPP作为有机催化剂，氰醇碳酸酯也可以快速制备。
• McIntosh, John M.; Cassidy, Kenneth C., Canadian Journal of Chemistry, 1991, vol. 69, # 8, p. 1315 - 1319
  作者：McIntosh, John M.、Cassidy, Kenneth C.

  DOI：——

  日期：——