4-(羟甲基)环己烷-1-腈 | 39779-20-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-(羟甲基)环己烷-1-腈
• 英文名称: 4-(hydroxymethyl)cyclohexanecarbonitrile
• 英文别名: trans-4-cyanocyclohexylmethanol；4-(Hydroxymethyl)cyclohexane-1-carbonitrile
• CAS: 39779-20-9
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: GRPCILYSCDCPJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(羟甲基)环己烷-1-腈 、 (2R)-2-[[(4-氯苯基)磺酰基]氨基]-5,5,5-三氟-戊酰胺 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以1.8%的产率得到(R)-2-{4-chloro-N-{[(1r,4r)-4-cyanocyclohexyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide
  参考文献：
  名称：

  Application of the Bicyclo[1.1.1]pentane Motif as a Nonclassical Phenyl Ring Bioisostere in the Design of a Potent and Orally Active γ-Secretase Inhibitor

  摘要：

  Replacement of the central, para-substituted fluorophenyl ring in the gamma-secretase inhibitor 1 (BMS-708,163) with the bic-yclo[1.1.1]pentane motif led to the discovery of compound 3, an equipotent enzyme inhibitor with significant improvements in passive permeability and aqueous solubility. The modified biopharmaceutical properties of 3 translated into excellent oral absorption characteristics (similar to 4-fold up arrow C-max and AUC values relative to 1) in a mouse model of gamma-secretase inhibition. In addition, SAR studies into other fluorophenyl replacements indicate the intrinsic advantages of the bicyclo[1.1.1]pentane moiety over conventional phenyl ring replacements with respect to achieving an optimal balance of properties (e.g., gamma-secretase inhibition, aqueous solubility/permeability, in vitro metabolic stability). Overall, this work enhances the scope of the [1.1.1]-bicycle beyond that of a mere "spacer" unit and presents a compelling case for its broader application as a phenyl group replacement in scenarios where the aromatic ring count impacts physicochemical parameters and overall drug-likeness.

  DOI：

  10.1021/jm300094u
• 作为产物：
  描述：

  4-formylcyclohexane-1-carbonitrile 以 methanolic potassium hydroxide 、 水 、 乙酸乙酯 为溶剂， 以1.22 g (90%)的产率得到4-(羟甲基)环己烷-1-腈
  参考文献：
  名称：

  Liquid crystalline esters and mixtures

  摘要：

  化合物的公式为##STR1##其中X.sup.2是一个单共价键或--COO--; X.sup.1是一个单共价键，--COO--, --CH.sub.2 CH.sub.2 --或当X.sup.2是--COO--时，X.sup.1也可以是p--C.sub.6 H.sub.4 --, p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4, p--C.sub.6 H.sub.4 --COO--或--COO--p--C.sub.6 H.sub.4; 环A是苯环或反-1,4-环己亚烷; 环B是苯环或当X.sup.2是--COO--且X.sup.1是一个单共价键，--COO--或--CH.sub.2 CH.sub.2 --时，环B也可以是反-1,4-环己亚烷; Z.sup.1，Z.sup.2和Z.sup.3分别是氢或当位于不通过单共价键直接与另一个环连接的苯环上时，Z.sup.1，Z.sup.2和Z.sup.3也可以是卤素，氰基或甲基; Y.sup.2是氰基，硝基，2,2-二氰乙烯基或当Y.sup.1是氢时，Y.sup.2也可以是2,2-二氰基-1-甲基乙烯基; Y.sup.1是卤素，氰基，C.sub.1-C.sub.3-烷基或当X.sup.1包括苯环或--COO--或Y.sup.2是硝基或Z.sup.1和Z.sup.2中至少一个不是氢时，Y.sup.1也可以是氢; 和R.sup.1是C.sub.1-C.sub.12-烷基或当位于苯环上时，R.sup.1也可以是C.sub.1-C.sub.12-烷氧基，其制备和在液晶混合物中的用途被描述。

  公开号：

  US04550981A1

文献信息

• Liquid crystal mixture
  申请人：Hoffmann-La Roche Inc.

  公开号：US04460770A1

  公开（公告）日：1984-07-17

  There is described a liquid crystalline mixture for electro-optical devices which are operated according to the two-frequency matrix addressing procedure. The mixture consists of three components A, B and C, each of which contains one or more compounds. Component A has a viscosity of at most about 40 cp, a clearing point of at least about 40.degree. C. and a dielectric anisotropy between about -2 and about +1. Component B has a dielectric anisotropy below about -2 and component C has a dielectric anisotropy above about +10, a clearing point of at least about 100.degree. C. and there is a cross-over frequency in the total mixture of at most about 15 kHz at 20.degree. C. Novel compounds for such mixtures and their manufacture and use are also described. The novel mixtures make possible especially high multiplex rates and short response times.

  描述了一种用于电光设备的液晶混合物，其根据双频矩阵寻址程序进行操作。该混合物由三个成分A、B和C组成，每个成分中含有一个或多个化合物。成分A的粘度最多约为40厘波，清晰点至少约为40摄氏度，介电各向异性在约-2到约+1之间。成分B的介电各向异性低于约-2，成分C的介电各向异性高于约+10，清晰点至少约为100摄氏度，在总混合物中20摄氏度时交叉频率最多约为15千赫。还描述了用于这种混合物的新化合物及其制造和使用。这种新型混合物使得特别高的多路复用速率和短的响应时间成为可能。
• Esters
  申请人：Hoffman-La Roche Inc.

  公开号：US04708441A1

  公开（公告）日：1987-11-24

  Compounds of the formula ##STR1## wherein X.sup.2 is a single covalent bond or --COO--; X.sup.1 is a single covalent bond, --COO--, --CH.sub.2 CH.sub.2 -- or when X.sup.2 is --COO--, X.sup.1 also can be p--C.sub.6 H.sub.4 --, p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4, p--C.sub.6 H.sub.4 --COO-- or --COO--p--C.sub.6 H.sub.4 ; ring A is a benzene ring or trans-1,4-cyclohexylene; ring B is a benzene ring or when X.sup.2 is --COO-- and X.sup.1 is a single covalent bond, --COO-- or --CH.sub.2 CH.sub.2 --, ring B also can be trans-1,4-cyclohexylene; Z.sup.1, Z.sup.2 and Z.sup.3 individually are hydrogen or when positioned on a benzene ring which is not linked directly with a further ring via a single covalent bond, Z.sup.1, Z.sup.2 and Z.sup.3 also can be halogen, cyano or methyl; Y.sup.2 is cyano, nitro, 2,2-dicyanovinyl or when Y.sup.1 is hydrogen Y.sup.2 also can be 2,2-dicyano-1-methylvinyl; Y.sup.1 is halogen, cyano, C.sub.1 -C.sub.3 -alkyl or, when X.sup.1 includes a benzene ring of --COO-- or Y.sup.2 is nitro or at least one of Z.sup.1 and Z.sup.2 is other than hydrogen, Y.sup.1 also can be hydrogen; and R.sup.1 is C.sub.1 -C.sub.12 -alkyl or when positioned on a benzene ring R.sup.1 also can be C.sub.1 -C.sub.12 -alkoxy, their manufacture and use in liquid crystalline mixtures are described.

  化合物的化学式为 ##STR1## 其中 X.sup.2 是单个共价键或--COO--; X.sup.1 是单个共价键，--COO--，--CH.sub.2 CH.sub.2 --或当 X.sup.2 为--COO--时，X.sup.1 也可以是p--C.sub.6 H.sub.4 --，p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 --，--CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4，p--C.sub.6 H.sub.4 --COO--或--COO--p--C.sub.6 H.sub.4; 环A是苯环或反-1,4-环己烷基; 环B是苯环或当X.sup.2为--COO--且X.sup.1是单个共价键，--COO--或--CH.sub.2 CH.sub.2 --时，环B也可以是反-1,4-环己烷基; Z.sup.1，Z.sup.2和Z.sup.3分别是氢或当位于不通过单个共价键直接与另一个环相连的苯环上时，Z.sup.1，Z.sup.2和Z.sup.3也可以是卤素，氰基或甲基; Y.sup.2是氰基，硝基，2,2-二氰基乙烯基或当Y.sup.1为氢时，Y.sup.2也可以是2,2-二氰基-1-甲基乙烯基; Y.sup.1是卤素，氰基，C.sub.1-C.sub.3烷基或当X.sup.1包括--COO--的苯环或Y.sup.2为硝基或至少有一个Z.sup.1和Z.sup.2不是氢时，Y.sup.1也可以是氢; R.sup.1是C.sub.1-C.sub.12烷基或当位于苯环上时，R.sup.1也可以是C.sub.1-C.sub.12烷氧基。描述了它们的制造和在液晶混合物中的使用。
• PETRZILKA, M.
  作者：PETRZILKA, M.

  DOI：——

  日期：——
• Flüssigkristalle mit Alkenyl- oder Alkenyloxygruppen
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0168683B1

  公开（公告）日：1990-11-28
• Flüssigkristalline Gemische enthaltend Komponenten mit einer 4-Alkenyl- oder 2Z-Alkenyl-Seitenkette
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0167912B1

  公开（公告）日：1990-01-03