3-ethyl-2-phenyl-3-pentanol

• 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: 3-ethyl-2-phenyl-3-pentanol
• 英文别名: 3-Ethyl-2-phenylpentan-3-ol
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: DEJRITRBLCHADO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-methyl-N-(1-phenylethyl)amine 在 萘 、 lithium 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-ethyl-2-phenyl-3-pentanol
  参考文献：
  名称：

  Generation of allylic and benzylic organolithium reagents from the corresponding ester, amide, carbonate, carbamate and urea derivatives

  摘要：

  The reaction of different allylic and benzylic non-enolisable esters or amides (1), carbonates (4), carbamates (6, 7) and ureas (8) with an excess of lithium powder and a catalytic amount of naphthalene (10%) in the presence of an electrophile [iPrCHO, tBuCHO, PhCHO, Me2CO, Et2CO, (CH2)(5)CO, Ph2CO, MeSiCl] in THF at different temperatures (-78, -30 or 0 degrees C) leads, after hydrolysis with water, to the corresponding allylated or benzylated products (2). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00610-9

文献信息

• Generation of allylic and benzylic organolithium compounds by fluorine–lithium exchange: reaction with electrophiles
  作者：David Guijarro、Miguel Yus

  DOI：10.1016/s0022-328x(00)00770-1

  日期：2001.4

  lithiation methodology to allylic and benzylic fluorides 1 led to the corresponding allylic and benzylic organolithium reagents, which, in the presence of different electrophiles (Barbier-type reaction conditions), afforded the expected products 2 in moderate yields. The procedure was useful for the transformation of primary, secondary and tertiary benzylic fluorides into the corresponding lithium

  萘催化的锂化方法在烯丙基和苄基氟化物1上的应用产生了相应的烯丙基和苄基有机锂试剂，在不同的亲电试剂存在下（Barbier型反应条件），以中等收率提供了预期的产物2。该方法可用于将伯，仲和叔苄基氟化物转化为相应的锂衍生物。当使用两步锂化工艺时（用锂和催化量的萘处理氟化物1，然后添加亲电试剂），仅形成了Wurtz型偶联产物。
• DTBB-Catalysed dilithiation of styrene and its methyl-derivatives: introduction of two electrophilic reagents
  作者：Miguel Yus、Pedro Martı́nez、David Guijarro

  DOI：10.1016/s0040-4020(01)01063-8

  日期：2001.12

  Pr2CO], in THF, at temperatures ranging from −78 to 0°C, gave, after hydrolysis, products 2 resulting from addition of lithium to the olefinic double bond and successive trapping with the electrophilic reagent. When a carbonyl compound was used as electrophile, mixtures of the monoaddition–reduction compounds 3 and 4 were obtained as by-products, which could be easily separated from the diaddition

  苯乙烯和一些甲基取代的苯乙烯1与锂和催化量的4,4'-二叔丁基联苯（DTBB）在几种亲电试剂[Me 3 SiCl，Me 2 CO，Et 2 CO， （CH 2）5 CO，Pr 2 CO]在THF中，于-78至0°C的温度范围内，水解后得到由锂加成至烯烃双键并随后用亲电子试剂捕获而得到的产物2。当羰基化合物用作亲电试剂时，单加成还原化合物3和4的混合物获得的副产物可以容易地与二价产物2分离。
• Highly regioselective reaction of zirconocene-alkene complexes with aldehydes or ketones
  作者：Noriyuki Suzuki、Christophe J. Rousset、Koichiro Aoyagi、Martin Kotora、Tamotsu Takahashi、Maki Hasegawa、Yu Nitto、Masahiko Saburi

  DOI：10.1016/0022-328x(94)80112-6

  日期：1994.6

  Reactions of zirconocene-alkene complexes Cp2Zr(CH2CHR)(PR′3) (R  H, Me, Et, SiR″3 or Ar) with aldehydes or ketones were investigated. Zirconocene-ethylene, -propylene or 1-butene complexes reacted with aldehydes or ketones at terminal carbons of alkenes to give the corresponding alcohols after hydrolysis with a high regioselectivity. A similar type of reaction product was also obtained by a reaction

  的锆-烯烃络合物的Cp反应2的Zr（CH 2 CHR）（PR' 3）（RH，ME等，先生“ 3或Ar）与醛或酮的关系进行了研究。锆茂-乙烯，-丙烯或1-丁烯络合物在烯烃的末端碳上与醛或酮反应，在水解后具有高区域选择性，得到相应的醇。氧化锆环戊烷与醛的反应也获得了相似类型的反应产物。该反应通过锆碳环戊烷的β-β'碳-碳键裂解进行。锆茂-乙烯基硅烷络合物与酮的反应得到具有优异区域选择性的3-三甲基甲硅烷基-1-氧杂-2-氧化锆环戊烷。碳-碳键的形成仅发生在乙烯基硅烷的末端碳上。水解后得到它们相应的γ-甲硅烷基醇。产物表明，乙烯基硅烷与β-碳上的羰基化合物反应生成甲硅烷基。它与乙烯基硅烷的常规反应形成鲜明对比，后者的α-碳通常会侵蚀亲电体。苯乙烯及其衍生物与戊烷-3-酮在锆上的反应产生了两种区域异构体的混合物。在1-氧杂-2-氧化锆环戊烷中，烯烃的取代基倾向于位于Zr的α位。该取向显示了由锆
• Direct transformation of allylic and benzylic alcohols or their silylated derivatives into organolithium compounds
  作者：Emma Alonso、David Guijarro、Miguel Yus

  DOI：10.1016/0040-4020(95)00709-h

  日期：1995.10

  The reaction of allylic or benzylic alcohols 1 with n-butyllithium followed by treatment with lithium powder and a catalytic amount of DTBB (5 mol %) in THF at room temperature gives a solution of the corresponding alkyllithium reagent, which reacts in situ with different electrophiles to yield the expected products 2. Alternatively, the O-silylated derivatives of the same alcohols are lithiated under Barbier-type reaction conditions to afford the same reaction products with better yields.
• Reductive opening of 2-phenyl-1,3-dioxolanes by a naphthalene-catalysed lithiation: synthetic applications
  作者：Juan F. Gil、Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4020(01)80223-4

  日期：——

  The reaction of 2-phenyl-1,3-dioxolanes 1a,b with an excess of lithium powder in the presence of a catalytic amount of naphthalene (4 mol %) in tetrahydrofuran at -40-degrees-C followed by successive reaction with an electrophile and final hydrolysis with water at the same temperature yields the corresponding monoprotected 1,2-diols 2aa-2bf. The same process but allowing to rise the temperature to 20-degrees-C before the hydrolysis affords alcohols 3aa-3bd. The use of 2,2-diphenyl-1,3-dioxolane 1d, under similar reaction conditions as for compounds 2, permits the isolation of 2,2-diphenylalcohols 11da-11dc, resulting from the reaction with two different electrophiles. A mechanistic rationalization for all processes is given.