5-苯基戊烷-2-醇 | 2344-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-苯基戊烷-2-醇
• 英文名称: 5-phenylpentan-2-ol
• 英文别名: 5-phenyl-2-(R,S)-pentanol
• CAS: 2344-71-0
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: ZFVFQRLBTBBQSK-UHFFFAOYSA-N

物化性质

• 沸点：
  251.73°C (rough estimate)
• 密度：
  0.9643

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2906299090

反应信息

• 作为反应物：
  描述：

  5-苯基戊烷-2-醇 在 双氧水 、 苯磺酸 、 potassium bromide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以87%的产率得到5-苯基戊烷-2-酮
  参考文献：
  名称：

  碱金属溴化物作为溴化物催化剂对醇的选择性氧化：反应机理的实验研究

  摘要：

  开发了溴化物催化的醇的氧化反应，该氧化反应在碱金属溴化物和氧化剂的存在下于温和的条件下进行。该反应涉及使用KBr和Oxone进行无有机分子的氧化，以及使用KBr和H 2 O 2水溶液进行布朗斯台德酸辅助氧化，以高收率提供各种羰基化合物。而且，在TEMPO存在下，在两种反应条件下，溴化物催化的伯醇的氧化使得羧酸和醛的发散合成成为可能。在各种机理研究的基础上，提出了一种可能的催化机理。

  DOI：

  10.1021/jo5008064
• 作为产物：
  描述：

  3-苯丙烯溴酸酯 在 盐酸 、 锌 、 2-碘酰基苯甲酸 作用下， 以 乙醚 、 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 5-苯基戊烷-2-醇
  参考文献：
  名称：

  Iron-Catalyzed Arene Alkylation Reactions with Unactivated Secondary Alcohols

  摘要：

  A simple, iron-based catalytic system allows for the inter- and intramolecular arylation of unactivated secondary alcohols. This transformation expands the substrate scope beyond the previously required activated alcohols and proceeds under mild reaction conditions, tolerating air and moisture. Furthermore, the use of an enantioenriched secondary alcohol provides an enantioenriched product for the intramolecular reaction, thereby offering a convenient approach to nonracemic products.

  DOI：

  10.1021/ol500606d

文献信息

• Facile oxidative conversion of alcohols to esters using molecular iodine
  作者：Naoshi Mori、Hideo Togo

  DOI：10.1016/j.tet.2005.03.097

  日期：2005.6

  A simple, efficient, and high-yield procedure for the oxidative conversion of alcohols to various types of esters and ketones, with molecular iodine and potassium carbonate was successfully carried out.

  成功地进行了一种简单，高效且高收率的方法，将醇与分子碘和碳酸钾氧化转化为各种类型的酯和酮。
• 9-Hydroxydibenzo[b,d]pyrans and intermediates
  申请人：Pfizer Inc.

  公开号：US04143139A1

  公开（公告）日：1979-03-06

  9-Hydroxydibenzo[b,d]pyrans useful as analgesics, hypotensives, immunosuppressants, tranquilizers; as anti-secretory and anti-anxiety drugs; intermediates therefor and derivatives thereof having the formulae ##STR1## wherein R is hydrogen or alkanoyl having from one to five carbon atoms; R.sub.1 is hydrogen, alkanoyl having from one to five carbon atoms or --CO--(CH.sub.2).sub.P --NR.sub.2 R.sub.3 wherein p is 0 or an integer from 1 to 4; each of R.sub.2 and R.sub.3 when taken individually is hydrogen or alkyl having from one to four carbon atoms; R.sub.2 and R.sub.3 when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from one to four carbon atoms in the alkyl group; Each of R.sub.4 and R.sub.5 is hydrogen, methyl or ethyl; R.sub.0 is oxo or alkylenedioxy having from two to four carbon atoms; Z is (a) alkylene having from one to nine carbon atoms; (b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n --wherein each of (alk.sub.1) and (alk.sub.2) has from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 9; Each of m and n is 0 or 1; X is O, S, SO or SO.sub.2 ; and W is methyl, phenyl, p-chlorophenyl, p-fluorophenyl, pyridyl, piperidyl, cycloalkyl having from 3 to 7 carbon atoms, or monosubstituted cycloalkyl wherein the substituent is phenyl, p-chlorophenyl or p-fluorophenyl; With the proviso that when W is methyl, Z is --(alk.sub.1).sub.m --X---(alk.sub.2).sub.n --.

  9-羟基二苯并[b,d]吡喃可用作镇痛剂、降压药、免疫抑制剂、镇静剂；作为抗分泌和抗焦虑药物；其中间体和具有以下式的衍生物 ##STR1## 其中R为氢或具有一至五个碳原子的烷酰基；R.sub.1为氢、具有一至五个碳原子的烷酰基或--CO--(CH.sub.2).sub.P --NR.sub.2 R.sub.3，其中p为0或1至4的整数；当单独考虑R.sub.2和R.sub.3时，R.sub.2和R.sub.3分别为氢或具有一至四个碳原子的烷基；当R.sub.2和R.sub.3与它们连接的氮一起形成与哌啶基、吡咯基、吡咯啉基、吗啉基和N-烷基哌嗪基中的一种所选的5-或6-成员杂环环；R.sub.4和R.sub.5中的每一个为氢、甲基或乙基；R.sub.0为氧代或具有二至四个碳原子的烷二氧基；Z为(a)具有一至九个碳原子的烷基；(b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n --其中每个(alk.sub.1)和(alk.sub.2)具有1至9个碳原子，但要求(alk.sub.1)加(alk.sub.2)中碳原子的总和不大于9；m和n中的每一个为0或1；X为O、S、SO或SO.sub.2；W为甲基、苯基、对氯苯基、对氟苯基、吡啶基、哌啶基、具有3至7个碳原子的环烷基，或单取代环烷基，其中取代基为苯基、对氯苯基或对氟苯基；但要求当W为甲基时，Z为--(alk.sub.1).sub.m --X---(alk.sub.2).sub.n --。
• Selective Oxidation of Alcohols with Alkali Metal Bromides as Bromide Catalysts: Experimental Study of the Reaction Mechanism
  作者：Katsuhiko Moriyama、Misato Takemura、Hideo Togo

  DOI：10.1021/jo5008064

  日期：2014.7.3

  A bromide-catalyzed oxidation of alcohols was developed which proceeded in the presence of an alkali metal bromide and an oxidant under mild conditions. The reaction involved an organic-molecule-free oxidation using KBr and Oxone and a Brønsted acid assisted oxidation using KBr and aqueous H2O2 solution to provide a broad range of carbonyl compounds in high yields. Moreover, the bromide-catalyzed oxidation

  开发了溴化物催化的醇的氧化反应，该氧化反应在碱金属溴化物和氧化剂的存在下于温和的条件下进行。该反应涉及使用KBr和Oxone进行无有机分子的氧化，以及使用KBr和H 2 O 2水溶液进行布朗斯台德酸辅助氧化，以高收率提供各种羰基化合物。而且，在TEMPO存在下，在两种反应条件下，溴化物催化的伯醇的氧化使得羧酸和醛的发散合成成为可能。在各种机理研究的基础上，提出了一种可能的催化机理。
• Visible-Light-Induced C–O Bond Formation for the Construction of Five- and Six-Membered Cyclic Ethers and Lactones
  作者：Honggu Im、Dahye Kang、Soyeon Choi、Sanghoon Shin、Sungwoo Hong

  DOI：10.1021/acs.orglett.8b03166

  日期：2018.12.7

  Visible-light-induced intramolecular C–O bond formation was developed using 2,4,6-triphenylpyrylium tetrafluoroborate (TPT), which allows the regiocontrolled construction of cyclic ethers and lactones. The reaction is likely to proceed through the single-electron oxidation of the phenyl group, followed by the formation of a benzylic radical, thus preventing a competing 1,5-hydrogen abstraction pathway

  可见光诱导的分子内C-O键的形成是使用2,4,6-三苯基吡啶鎓四氟硼酸酯（TPT）进行的，该化合物可进行区域控制的环醚和内酯的构建。该反应可能通过苯基的单电子氧化进行，然后形成苄基，从而阻止竞争的1,5-氢提取途径。详细的机理研究表明，分子氧可用于捕获自由基中间体以形成苯甲醇，然后将其进行环化。通过使用统一协议提供对有价值的五元和六元环醚和内酯的有效访问，此新方法可作为强大的平台。
• Bicyclic benzo fused compounds
  申请人：Pfizer Inc.

  公开号：US04486428A1

  公开（公告）日：1984-12-04

  Bicyclic fused benzenoid compounds of the formula ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, where M is O, CH.sub.2 or NR.sub.6 ; R.sub.6 is hydrogen, formyl, carbobenzyloxy or certain carboalkoxyalkyl, alkanoyl, alkyl, aralkyl or aralkylcarbonyl groups; A' is: (1) A where one of A and B is hydrogen such that when A is hydrogen, B is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 1 or 2; when B is hydrogen, A is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 0 or 1, when taken together A and OR.sub.1 form a lactone or certain derivatives thereof; (2) A' is ##STR2## (3) A' is Q.sub.3 ; Q is CO.sub.2 R.sub.7, COR.sub.8, C(OH)R.sub.8 R.sub.9, CN, CONR.sub.12 R.sub.13, CH.sub.2 NR.sub.12 R.sub.13, CH.sub.2 NHCOR.sub.14, CH.sub.2 NHSO.sub.2 R.sub.17 or 5-tetrazoyl; Q.sub.3 is ##STR3## 5-tetrazolyl, CH.sub.2 CONHCOR.sub.7, COOH or certain ester, amide, carboximido or sulfonimido derivatives thereof, CONHOH, CONHCONH.sub.2, or COCH.sub.2 Q.sub.4 where Q.sub.4 is CN or COOH or certain esters thereof; R.sub.1 is hydrogen, benzyl or certain acyl groups; R.sub.4 is hydrogen, certain alkyl or certain aralkyl groups; R.sub.5 is hydrogen or certain alkyl groups; Z is (C.sub.1 -C.sub.9)alkylene, optionally interrupted by O, S, SO or SO.sub.2 ; and W is hydrogen, methyl, certain aryl or cycloalkyl groups; useful in mammals as analgesics, tranquilizers, antiemetic agents, diuretics, anticonvulsants, antidiarrheals, antitussives, in treatment of glaucoma, and intermediates therefore.

  公式为##STR1##的双环融合苯类化合物及其药学上可接受的阳离子和酸盐，其中M为O、CH.sub.2或NR.sub.6；R.sub.6为氢、甲酰基、羟甲基苄氧基或某些羧烷氧基烷基、烷酰基、烷基、芳基烷基或芳基烷基羰基基团；A'为：(1) A，其中A和B中的一个为氢，使得当A为氢时，B为C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q且f为1或2；当B为氢时，A为C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q且f为0或1，当A和OR.sub.1一起形成内酯或其某些衍生物时；(2) A'为##STR2##(3) A'为Q.sub.3；Q为CO.sub.2 R.sub.7、COR.sub.8、C(OH)R.sub.8 R.sub.9、CN、CONR.sub.12 R.sub.13、CH.sub.2 NR.sub.12 R.sub.13、CH.sub.2 NHCOR.sub.14、CH.sub.2 NHSO.sub.2 R.sub.17或5-四唑基；Q.sub.3为##STR3##5-四唑基、CH.sub.2 CONHCOR.sub.7、COOH或其某些酯、酰胺、羧酰亚胺或磺酰亚胺衍生物，CONHOH、CONHCONH.sub.2或COCH.sub.2 Q.sub.4，其中Q.sub.4为CN或COOH或其某些酯；R.sub.1为氢、苄基或某些酰基；R.sub.4为氢、某些烷基或某些芳基烷基；R.sub.5为氢或某些烷基；Z为(C.sub.1-C.sub.9)烷基，可由O、S、SO或SO.sub.2中断；W为氢、甲基、某些芳基或环烷基；在哺乳动物中作为镇痛剂、镇静剂、止吐剂、利尿剂、抗癫痫药、止泻药、镇咳剂、治疗青光眼和其中间体。