cis-4-(benzyloxy)cyclohexanol | 127074-28-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-4-(benzyloxy)cyclohexanol
• 英文别名: cis-4-Benzyloxy-cyclohexanol
• CAS: 127074-28-6
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: GDGBMTDJFHTXID-BETUJISGSA-N

物化性质

• 沸点：
  321.9±35.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cis-4-(benzyloxy)cyclohexanol 在 caesium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 19.0h， 生成
  参考文献：
  名称：

  Optimizing Pyrazolopyrimidine Inhibitors of Calcium Dependent Protein Kinase 1 for Treatment of Acute and Chronic Toxoplasmosis

  摘要：

  Calcium dependent protein kinase 1 (CDPK1) is an essential Ser/Thr kinase that controls invasion and egress by the protozoan parasite Toxoplasma gondii. The Gly gatekeeper of CDPK1 makes it exquisitely sensitive to inhibition by small molecule 1H-pyrazolo[3,4-d]pyrimidine-4-amine (PP) compounds that are bulky ATP mimetics. Here we rationally designed, synthesized, and tested a series of novel PP analogs that were evaluated for inhibition of CDPK1 enzyme activity in vitro and parasite growth in cell culture. Optimal substitution on the PP scaffold included 2-pyridyl ethers directed into the hydrophobic pocket and small carbocyclic rings accessing the ribose-binding pocket. Further optimization of the series led to identification of the lead compound 3a that displayed excellent potency, selectivity, safety profile, and efficacy in vivo. The results of these studies provide a foundation for further work to optimize CDPK1 inhibitors for the treatment of acute and chronic toxoplasmosis.

  DOI：

  10.1021/acs.jmedchem.0c00419
• 作为产物：
  描述：

  ((cyclohex-3-enyloxy)methyl)benzene 在 lithium aluminium tetrahydride 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 cis-4-(benzyloxy)cyclohexanol
  参考文献：
  名称：

  Regiochemical control of the ring-opening of 1,2-epoxides by means of chelating processes. Synthesis and reactions of the cis- and trans-oxides derived from 4-(benzyloxy)cyclohexene

  摘要：

  DOI：

  10.1021/jo00301a011

文献信息

• [EN] COMPOUNDS AND COMPOSITIONS USEFUL FOR TREATING DISORDERS RELATED TO NTRK<br/>[FR] COMPOSÉS ET COMPOSITIONS UTILES POUR TRAITER DES TROUBLES ASSOCIÉS AU GÈNE NTRK
  申请人：BLUEPRINT MEDICINES CORP

  公开号：WO2017035354A1

  公开（公告）日：2017-03-02

  This invention relates to inhibitors of NTRK that are active against wild-type NTRK and its resistant mutants.

  这项发明涉及对NTRK的抑制剂，对野生型NTRK及其耐药突变体具有活性。
• Generalization, Alteration, and Enhancement of the Stereoselectivity in the Cieplak-Mode Reductions of 4-Alkoxy(or Silyloxy)cyclohexanones
  作者：Yoshimitsu Nagao、Michimasa Goto、Masahito Ochiai

  DOI：10.1246/cl.1990.1507

  日期：1990.9

  Reductions of 4-alkoxy(or silyloxy)cyclohexanones with LiAlH4, AlH(i-Bu)2, and Li(s-Bu)3BH afforded the corresponding cis alcohols in 73–80% selectivities. Similar reduction of 4-benzyloxy- and 4-t-butyldiphenylsilyloxy-cyclohexanones with AlH(i-Bu)2 in the presence of EtAlCl2 gave trans alcohol (93% selectivity) from the former and cis alcohol (94% selectivity) from the latter, respectively.

  用LiAlH4、AlH(i-Bu)2和Li(s-Bu)3BH还原4-烷氧基（或硅氧基）环己酮可以获得相应的顺式醇，选择性为73-80%。在EtAlCl2存在下，用AlH(i-Bu)2对4-苄氧基和4-t-丁基二苯基硅氧基环己酮进行类似还原，前者获得反式醇（选择性为93%），后者获得顺式醇（选择性为94%）。
• Trifluoromethyl-Substituted Indenyl Rhodium and Iridium Complexes Are Highly Selective Catalysts for Directed Hydroboration Reactions
  作者：John A. Brinkman、Tam T. Nguyen、John R. Sowa

  DOI：10.1021/ol005653z

  日期：2000.4.1

  Rhodium and iridium catalysts containing trifluoromethyl-substituted indenyl ligands (Ind'MCod, Ind' = C9H7, (1-CF3)C9H6, (2-CF3)C9H6, (1,3-CF3)2C9H5) have been developed for the directed hydroboration of 4-(benzyloxy)cyclohexene to cis-3-(benzyloxy)cyclohexanol. Compared to unsubstituted complexes, trifluoromethyl substitution yields a 3-10% increase in selectivity which is attributed to the strong

  已开发出含三氟甲基取代的茚基配体（Ind'MCod，Ind'= C9H7，（1-CF3）C9H6，（2- ） ，（1,3- ）2C9H5）的铑和铱催化剂4-（苄氧基）环己烯形成顺式-3-（苄氧基）环己醇。与未取代的配合物相比，三氟甲基取代的选择性提高了3-10％，这归因于三氟甲基的强大的吸电子作用。铑配合物的选择性为74-84％，铱配合物的选择性很高（93-98％）。
• Einige Derivate und Umwandlungsprodukte des Chinits
  作者：D. A. Prins

  DOI：10.1002/hlca.19570400609

  日期：——

  A preparative method is given for the partial benzylation of quinitol to 4-benzyloxy-cyclohexanol. This compound was oxidized to 4-benzyloxy-cyclohexanone, which on alkylation furnished methyl 5-benzyloxy-2-oxo-cyclohexylacetate.

  给出了一种制备方法，用于将奎尼醇部分苄基化为4-苄氧基-环己醇。将该化合物氧化为4-苄氧基-环己酮，其在烷基化时提供乙酸甲基5-苄氧基-2-氧-环己酯。
• Compounds and compositions useful for treating disorders related to NTRK
  申请人：BLUEPRINT MEDICINES CORPORATION

  公开号：US10017512B2

  公开（公告）日：2018-07-10

  This disclosure relates to inhibitors of NTRK that are active against wild-type NTRK and its resistant mutants, such as compounds of Formula (I):

  本公开涉及对野生型 NTRK 及其抗性突变体有活性的 NTRK 抑制剂，如式 (I) 化合物：