trans-3-(benzyloxy)cyclohexanol | 114738-00-0

• 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: trans-3-(benzyloxy)cyclohexanol
• 英文别名: 3-(benzyloxy)cyclohexan-1-ol；(1R*,3R*)-3-(benzyloxy)cyclohexan-1-ol；(1S,3S)-3-phenylmethoxycyclohexan-1-ol
• CAS: 114738-00-0
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: RFCYVWGCOXVSBD-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  trans-3-(benzyloxy)cyclohexanol 在 chromium(VI) oxide 作用下， 以 丙酮 为溶剂， 以20 mg的产率得到3-(苄氧基)环己酮
  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
• 作为产物：
  描述：

  [(cyclohex-2-en-1-yloxy)methyl]benzene 在 lithium aluminium tetrahydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 正戊烷 为溶剂， 反应 1.0h， 生成 trans-3-(benzyloxy)cyclohexanol
  参考文献：
  名称：

  通过螯合方法对1,2-环氧化物的开环进行区域化学控制。8.衍生自3-苄氧基环己烯和2-苄氧基-5,6-二氢-2 H-吡喃的顺式和反式氧化物的合成和开环反应

  摘要：

  在具有在环氧乙烷环的烯丙基位置上具有极性官能团的环状环氧乙烷体系中，证实了通过金属离子辅助的螯合过程通过极性远程官能化而带有极性远程官能化的1,2-环氧化物的开环的区域化学结果。非对映体顺式/反式环氧化物对5,6和7,8由3- benzyloxycyclohexene衍生，和2-苄氧基- 5,6-二氢-2 H ^ -吡喃，分别制备和几个其开口的反应进行了研究。观察到的区域选择性在很大程度上取决于反应条件（标准条件或金属辅助条件），并且有趣地取决于所用亲核试剂的性质。

  DOI：

  10.1016/s0040-4020(01)81219-9

文献信息

• Intramolecular hypervalent tin-oxygen interaction. The origin for fixation of six-membered carbocycles to the 1,3-diaxial conformer and for stereoselective osmylations
  作者：Masahito. Ochiai、Shigeru. Iwaki、Tatsuzo. Ukita、Yoshiki. Matsuura、Motoo. Shiro、Yoshimitsu. Nagao

  DOI：10.1021/ja00222a020

  日期：1988.7

  L'interaction diaxiale-1,3 permet une haute stereoselectivite dans l'osmylation de l'ethyleneacetal de la trimethylstannyl-5 cyclohexene-2one

  L'interaction diaxiale-1,3 permet une 高级立体选择性 dans l'osmylation de l'ethyleneacetal de la trimethylstannyl-5 cyclohexene-2one
• 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％）。
• Rhodium(I)-catalyzed hydroboration of olefins. The documentation of regio- and stereochemical control in cyclic and acyclic systems
  作者：David A. Evans、Gregory C. Fu、Amir H. Hoveyda

  DOI：10.1021/ja00228a068

  日期：1988.9

  Catalyse par les complexes Rh(PPh 3 ) 3 Cl et [Rh(nbd)(diphos-4)]BF 4 (nbd=norbornadiene, diphos-4=bis-diphenylphosphino-1,4 butane)

  催化复合物 Rh(PPh 3 ) 3 Cl et [Rh(nbd)(diphos-4)]BF 4 (nbd=降冰片二烯，diphos-4=双-二苯基膦基-1,4丁烷)
• Origin of High Diastereoselectivity in Reactions of Seven‐Membered‐Ring Enolates
  作者：Olga Lavinda、Collin H. Witt、K. A. Woerpel

  DOI：10.1002/anie.202114183

  日期：2022.3.28

  The diastereoselective reactions of chiral seven-membered-ring enolates have been systematically investigated. Diastereoselectivity was found to be general for ϵ-lactams, ϵ-lactones, and cycloheptanones with various substituent patterns. Computational investigations provided insight into the origin of the diastereoselectivity. A model for predicting the stereochemistry of seven-membered-ring enolate

  手性七元环烯醇化物的非对映选择性反应已被系统研究。发现对于具有各种取代基模式的ε-内酰胺、ε-内酯和环庚酮来说，非对映选择性是普遍的。计算研究提供了对非对映选择性起源的深入了解。提出了预测七元环烯醇化物烷基化立体化学的模型。
• Targeting Mobilization of Ferrous Iron in <i>Pseudomonas aeruginosa</i> Infection with an Iron(II)-Caged LpxC Inhibitor
  作者：Brian R. Blank、Poulami Talukder、Ryan K. Muir、Erin R. Green、Eric P. Skaar、Adam R. Renslo

  DOI：10.1021/acsinfecdis.9b00057

  日期：2019.8.9

  Iron is essential to all life, and competition for this vital nutrient is central to host-pathogen interactions during infection. The opportunistic Gram-negative pathogen Pseudomonas aeruginosa utilizes a diverse array of iron-acquisition strategies, including those enabling import of extracellular ferrous iron. We hypothesize that soluble and redox-active ferrous iron can be employed to activate caged antibiotics at sites of infection in vivo. Here we describe new chemistry that expands the application of our laboratory's Fe2+-activated-prodrug chemistry to cage hydroxamic acids, a class of drugs that present manifold development challenges. We synthesize the caged form of a known LpxC inhibitor and show that it is efficacious in an acute P. aeruginosa mouse-lung infection model, despite showing little activity in cell-culture experiments. Overall, our results are consistent with the Fe2+-promoted uncaging of an antibacterial payload at sites of infection in an animal and lend support to recent reports indicating that extracellular pools of ferrous iron can be utilized by bacterial pathogens like P. aeruginosa during infection.