4-((tert-butyldimethylsilyl)oxy)cyclohexanecarbonitrile | 1202009-17-3

• 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: 4-((tert-butyldimethylsilyl)oxy)cyclohexanecarbonitrile
• 英文别名: 4-OTBS cyclohexanecarbonitrile；4-(tert-butyl-dimethyl-silanyloxy)-cyclohexane-carbonitrile；4-[tert-butyl(dimethyl)silyl]oxycyclohexane-1-carbonitrile
• CAS: 1202009-17-3
• 化学式: C₁₃H₂₅NOSi
• 分子量: 239.433
• InChiKey: MQWZPRFUTHGYHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  4-((tert-butyldimethylsilyl)oxy)cyclohexanecarbonitrile 、 4-溴苯腈 在 (2,2,6,6-tetramethylhexahydropyridin-1-yl)zinc (II) lithium chloride 、 2-双环己基膦-2',6'-二甲氧基联苯 、 CCl₂CuLi₂N 、 palladium diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以71%的产率得到4-((1SR,4SR)-4-((tert-butyldimethylsilyl)oxy)-1-cyanocyclohexyl)benzonitrile
  参考文献：
  名称：

  Cyclohexylcarbonitriles: Diastereoselective Arylations with TMPZnCl·LiCl

  摘要：

  Deprotonating substituted cyclohexanecarbonitriles with TMPZnCl center dot LiCl affords zincated nitriles that diastereoselectively couple with aryl bromides in the presence of catalytic Pd(OAc)(2), and S-Phos. Steric and electronic effects influence the diastereoselectivity; 4-t-butyl-, 4-TBSO-, and 2-Me-cyclohexanecarbonitriles exert virtually complete diastereocontrol whereas modest diastereoselectivity is observed with 4-i-Pr-, 4-Me-, and 3-Me-cyclohexanecarbonitriles. The unusual diastereoselectivity trends should prove useful for synthesizing substituted cyclohexanecarbonitrile-containing pharmaceuticals.

  DOI：

  10.1021/jo301127n
• 作为产物：
  描述：

  4-氧代环己烷甲腈 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 4-((tert-butyldimethylsilyl)oxy)cyclohexanecarbonitrile
  参考文献：
  名称：

  [EN] SUBSTITUTED ISOQUINOLINES AND ISOQUINOLINONES AS RHO KINASE INHIBITORS
  [FR] ISOQUINOLINES ET ISOQUINOLINONES SUBSTITUÉES UTILISÉES COMME INHIBITEURS DE RHO-KINASE

  摘要：

  该发明涉及用于治疗和/或预防与Rho激酶和/或Rho激酶介导的肌球蛋白轻链磷酸酶磷酸化相关疾病的配方(I)的取代异喹啉和异喹啉酮，以及含有这种化合物的组合物。

  公开号：

  WO2009156100A1

文献信息

• SUBSTITUTED ISOQUINOLINES AND ISOQUINOLINONES AS RHO KINASE INHIBITORS
  申请人：Plettenburg Oliver

  公开号：US20110190341A1

  公开（公告）日：2011-08-04

  The invention relates to substituted isoquinoline and isoquinolinones of the formula (I) useful for the treatment and/or prevention of diseases associated with Rho-kinase and/or Rho-kinase mediated phosphorylation of myosin light chain phosphatase, and compositions containing such compounds.

  本发明涉及公式（I）的取代异喹啉和异喹啉酮，用于治疗和/或预防与Rho激酶和/或Rho激酶介导的肌球蛋白轻链磷酸酶的磷酸化相关的疾病，以及含有这些化合物的组合物。
• Substituted isoquinolines and isoquinolinones as Rho kinase inhibitors
  申请人：Plettenburg Oliver

  公开号：US08541449B2

  公开（公告）日：2013-09-24

  The invention relates to substituted isoquinoline and isoquinolinones of the formula (I) useful for the treatment and/or prevention of diseases associated with Rho-kinase and/or Rho-kinase mediated phosphorylation of myosin light chain phosphatase, and compositions containing such compounds.

  本发明涉及具有以下公式（I）的替代异喹啉和异喹啉酮，用于治疗和/或预防与Rho激酶和/或Rho激酶介导的肌球蛋白轻链磷酸酶磷酸化相关的疾病，以及含有这些化合物的组合物。
• Cyclohexylcarbonitriles: Diastereoselective Arylations with TMPZnCl·LiCl
  作者：Robert J. Mycka、Stéphanie Duez、Sebastian Bernhardt、Johannes Heppekausen、Paul Knochel、Fraser F. Fleming

  DOI：10.1021/jo301127n

  日期：2012.9.7

  Deprotonating substituted cyclohexanecarbonitriles with TMPZnCl center dot LiCl affords zincated nitriles that diastereoselectively couple with aryl bromides in the presence of catalytic Pd(OAc)(2), and S-Phos. Steric and electronic effects influence the diastereoselectivity; 4-t-butyl-, 4-TBSO-, and 2-Me-cyclohexanecarbonitriles exert virtually complete diastereocontrol whereas modest diastereoselectivity is observed with 4-i-Pr-, 4-Me-, and 3-Me-cyclohexanecarbonitriles. The unusual diastereoselectivity trends should prove useful for synthesizing substituted cyclohexanecarbonitrile-containing pharmaceuticals.
• [EN] SUBSTITUTED ISOQUINOLINES AND ISOQUINOLINONES AS RHO KINASE INHIBITORS<br/>[FR] ISOQUINOLINES ET ISOQUINOLINONES SUBSTITUÉES UTILISÉES COMME INHIBITEURS DE RHO-KINASE
  申请人：SANOFI AVENTIS

  公开号：WO2009156100A1

  公开（公告）日：2009-12-30

  The invention relates to substituted isoquinoline and isoquinolinones of the formula (I) useful for the treatment and/or prevention of diseases associated with Rho-kinase and/or Rho-kinase mediated phosphorylation of myosin light chain phosphatase, and compositions containing such compounds.

  该发明涉及用于治疗和/或预防与Rho激酶和/或Rho激酶介导的肌球蛋白轻链磷酸酶磷酸化相关疾病的配方(I)的取代异喹啉和异喹啉酮，以及含有这种化合物的组合物。