R-(+)-4-chloro-1-<4-(1,1-dimethylethyl)phenyl>-1-butanol | 151091-53-1

• 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: R-(+)-4-chloro-1-<4-(1,1-dimethylethyl)phenyl>-1-butanol
• 英文别名: (R)-1-(4-(tert-butyl)phenyl)-4-chlorobutan-1-ol；KSC-335-060；(1R)-1-(4-tert-butylphenyl)-4-chlorobutan-1-ol
• CAS: 151091-53-1
• 化学式: C₁₄H₂₁ClO
• 分子量: 240.773
• InChiKey: WOLKQAWPZRAYLD-CYBMUJFWSA-N

物化性质

• 沸点：
  350.4±37.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  R-(+)-4-chloro-1-<4-(1,1-dimethylethyl)phenyl>-1-butanol 在 三乙胺 、 sodium iodide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Structure-activity relationships within a series of analogues of the histamine H1-antagonist terfenadine

  摘要：

  A number of terfenadine derivatives including terfenadine enantiomers were synthesized and tested for histamine H-1-receptor affinity. No significant differences, in H-1 activity were found between terfenadine enantiomers. Qualitative structure-activity relationship studies identified the alpha,alpha-diphenyl-4-piperidinomethanol moiety as the pharmacophore for the H-1 activity of this group of compounds. The major role of die phenylbutanol moiety in terfenadine seems to be preventing the compound from crossing the blood-brain barrier.

  DOI：

  10.1016/0223-5234(93)90009-4
• 作为产物：
  描述：

  4'-叔丁基-4-氯丁酰苯 在 C₃₂H₃₃FeN₃O₂Si 、 silica gel 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 R-(+)-4-chloro-1-<4-(1,1-dimethylethyl)phenyl>-1-butanol
  参考文献：
  名称：

  超快铁催化还原功能化酮：卤代醇，氧杂杂环和氨基醇的高度对映选择性合成

  摘要：

  分子定义的手性boxmi铁烷基络合物催化各种官能化酮的氢硼化，并提供相应的手性卤代醇，氧杂杂环（环氧乙烷，氧杂环丁烷，四氢呋喃和二恶烷）和氨基醇，具有出色的对映选择性（高达> 99％ee）和转化效率在低催化剂负载量（低至0.5 mol％）下。在−30°C时，周转频率大于40000 h -1突显了这种富含地球的金属催化剂的活性，该催化剂可耐受许多官能团。

  DOI：

  10.1002/anie.201806196

文献信息

• METHODS AND COMPOSITIONS FOR TREATING INFECTION
  申请人：UNIVERSITY OF ROCHESTER

  公开号：US20150238473A1

  公开（公告）日：2015-08-27

  Provided herein are compositions and methods for treating or preventing infection.

  本文提供了用于治疗或预防感染的组合物和方法。
• Enzymatic preparation of optically active 4-chloro-1-phenyl-1-butanol derivatives
  作者：Daniele Bianchi、Paola Moraschini、Aldo Bosetti、Pietro Cesti

  DOI：10.1016/s0957-4166(00)86266-7

  日期：1994.10

  The enantiomers of substituted 4-chloro-1-phenyl-1-butanol were prepared by stereoselective lipase-catalyzed resolution of the corresponding esters and alcohols, in water and in organic solvent, respectively.

  取代的4-氯-1-苯基-1-丁醇的对映体分别通过立体选择性脂肪酶催化拆分相应的酯和醇，分别在水和有机溶剂中制备。
• Chemoselective and Divergent Synthesis of Chlorohydrins and Oxaheterocycles via Ir-Catalyzed Asymmetric Hydrogenation
  作者：Yan Zong、Xiaomei Zou、Jingyuan Song、Gen-Qiang Chen、Xumu Zhang

  DOI：10.1021/acs.orglett.3c02565

  日期：2023.9.22

  Chlorohydrins and oxaheterocycles are synthetically valuable building blocks for diverse natural products and therapeutic substances. A highly efficient Ir/f-phamidol-catalyzed asymmetric hydrogenation of ω-chloroketones was successfully developed, and various chlorohydrins and oxaheterocycles were obtained divergently with excellent yields and enantioselectivities (up to >99% yield and >99% ee). Synthetic

  氯醇和氧杂环是多种天然产物和治疗物质的具有合成价值的结构单元。成功开发了高效的Ir/ f-邻氨基醇催化的ω-氯酮不对称氢化反应，并以优异的产率和对映选择性（高达>99%产率和>99%ee）不同地获得了各种氯代醇和氧杂环。通过这种催化方法对几种对映体富集的药物的关键中间体进行克级合成，证明了这种发散转化的合成效用。
• Methods and compositions for treating infection
  申请人：UNIVERSITY OF ROCHESTER

  公开号：US10004701B2

  公开（公告）日：2018-06-26

  Provided herein are compositions and methods for treating or preventing infection.

  本文提供了用于治疗或预防感染的组合物和方法。
• Repurposing the Antihistamine Terfenadine for Antimicrobial Activity against <i>Staphylococcus aureus</i>
  作者：Jessamyn I. Perlmutter、Lauren T. Forbes、Damian J. Krysan、Katherine Ebsworth-Mojica、Jennifer M. Colquhoun、Jenna L. Wang、Paul M. Dunman、Daniel P. Flaherty

  DOI：10.1021/jm5010682

  日期：2014.10.23

  Staphylococcus aureus is a rapidly growing health threat in the U.S., with resistance to several commonly prescribed treatments. A high-throughput screen identified the antihistamine terfenadine to possess, previously unreported, antimicrobial activity against S. aureus and other Gram-positive bacteria. In an effort to repurpose this drug, structure-activity relationship studies yielded 84 terfenadine-based analogues with several modifications providing increased activity versus S. aureus and other bacterial pathogens, including Mycobacterium tuberculosis. Mechanism of action studies revealed these compounds to exert their antibacterial effects, at least in part, through inhibition of the bacterial type II topoisomerases. This scaffold suffers from hERG liabilities which were not remedied through this round of optimization; however, given the overall improvement in activity of the set, terfenadine-based analogues provide a novel structural class of antimicrobial compounds with potential for further characterization as part of the continuing process to meet the current need for new antibiotics.