2-苯基庚烷-3-醇 | 7661-43-0

• 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: 2-苯基庚烷-3-醇
• 英文名称: 2-Phenylheptan-3-ol
• CAS: 7661-43-0
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: XHJPWJPKYQJVFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  5
• 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

• 作为反应物：
  描述：

  2-苯基庚烷-3-醇 在 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-苯基-3-庚酮
  参考文献：
  名称：

  Ohta; Hiromichi; Iwabuchi, Tetsuya, Agricultural and Biological Chemistry, 1986, vol. 50, # 3, p. 725 - 732

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯基丙醛 在 RNa*CuCN*n-BuLi 作用下， 生成 2-苯基庚烷-3-醇
  参考文献：
  名称：

  gengenions对有机铜酸盐反应性/选择性的影响：高阶，混合的硫代氰基氰酸盐

  摘要：

  已经使用衍生自CuCN的试剂R T R R Cu（CN）LiNa以及有机锂（R T Li）和有机钠（R R Na）物种中的每一个当量来研究几种不同类型的有机铜酸盐特征反应。

  DOI：

  10.1016/s0040-4039(00)82475-2

文献信息

• Cram selectivity in the reaction of 2-phenylpropanal with alkyllithium reagents: Myth and reality
  作者：Manfred T. Reetz、Stephan Stanchev、Helmut Haning

  DOI：10.1016/s0040-4020(01)89872-0

  日期：1992.1

  The reaction of racemic 2-phenylpropanal with methyl- and n-butyllithium was studied in detail. Factors such as temperature, solvent, rate of addition, presence of salts, scale-up and source of reagents were carefully examined. Cram-selectivities of 90 –94% were routinely reached under standard conditions (THF, −78°C), which is significantly higher than previously reported for these classical reactions

  详细研究了外消旋2-苯基丙醛与甲基和正丁基锂的反应。仔细检查了诸如温度，溶剂，添加速率，盐的存在，放大比例和试剂来源等因素。在标准条件下（THF，-78°C），通常可以达到90-94％的Cram选择性，这比以前报道的这些经典反应要高得多。
• Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols
  作者：Karsten Donabauer、Mitasree Maity、Anna Lucia Berger、Gregory S. Huff、Stefano Crespi、Burkhard König

  DOI：10.1039/c9sc01356c

  日期：——

  present a redox-neutral method for the photocatalytic generation of carbanions. Benzylic carboxylates are photooxidized by single electron transfer; immediate CO2 extrusion and reduction of the in situ formed radical yields a carbanion capable of reacting with aliphatic aldehydes as electrophiles giving the Grignard analogous reaction product.

  我们提出了一种用于光催化产生碳负离子的氧化还原中性方法。苄基羧酸盐通过单电子转移被光氧化；立即CO 2挤出和原位形成的自由基的还原产生能够与作为亲电试剂的脂肪醛反应的碳负离子，从而产生格氏类似反应产物。
• Zirconium Mediated Regioselective Carbon-Carbon Bond Formation Reactions
  作者：Tamotsu Takahashi、Noriyuki Suzuki、Maki Hasegawa、Yu Nitto、Ko-ichiro Aoyagi、Masahiko Saburi

  DOI：10.1246/cl.1992.331

  日期：1992.2

  Reactions of zirconocene-alkene complexes with aldehydes gave alcohols as coupling products after hydrolysis. The carbon-carbon bond formation proceeded at C1 carbon of alkenes, in sharp contrast to the reactions of alkene-alkene coupling on zirconium. A similar alcohol was also obtained by the reaction of zirconacyclopentane with aldehyde after hydrolysis. Treatment of (C5Me5)2ZrEt2 with styrene gave

  锆茂-烯烃配合物与醛的反应在水解后得到醇作为偶联产物。碳-碳键的形成是在烯烃的 C1 碳上进行的，这与烯烃-烯烃偶联在锆上的反应形成鲜明对比。通过水解后的锆并环戊烷与醛反应也得到类似的醇。(C5Me5)2ZrEt2 用苯乙烯处理水解后得到 2-苯基丁烷，这与 Cp2ZrEt2 得到 1-苯基丁烷的情况相反。
• Samarium(II) Triflate as a New Reagent for the Grignard-Type Carbonyl Addition Reaction
  作者：Shin-ichi Fukuzawa、Keisuke Mutoh、Teruhisa Tsuchimoto、Tamejiro Hiyama

  DOI：10.1021/jo960260s

  日期：1996.1.1

  On treatment of a THF solution of Sm(OTf)(3) with 1 equiv of an organolithium or organomagnesium reagent-at ambient temperature, the purple or deep green solution of the divalent samarium triflate [Sm(OTf)(2)] was readily obtained. For this preparation, s-BuLi was the most effective as was evidenced by the reduction of a-phenylethyl iodide in the presence of HMPA. The Sm(OTf)(2) reagent mediated the Grignard-type reaction effectively in THF/HMPA; alkylation and allylation of ketones or aldehydes with alkyl, allyl, or benzyl halides proceeded via organosamarium intermediates. Diastereoselectivity of the samarium-Grignard reaction was examined using 2-methylcyclohexanone, 4-tert-butylcyclohexanone, and 2-phenylpropanal and was found to be higher in each case than that with SmI2. With 2-methylcyclohexanone, for example, Sm(OTf)(2) gave the greatest ratio of axial alcohol:equatorial alcohol = 99:1, and SmI2 gave a ratio of 91:9. Halides containing an ester or a silyl group were reactive in the Reformatsky- or Peterson-type reaction, respectively, using the Sm(OTf)(2) reagent.
• Effects of additives on cuprate 1,4-additions: Gilman reagents in the presence of Me3SiCN
  作者：Bruce H. Lipshutz、Brian James

  DOI：10.1016/s0040-4039(00)61676-3

  日期：1993.10

  Chemical and spectroscopic studies on Gilman cuprates R2CuLi.LiI in the presence of TMS-CN reveal the lack of independence of these species in THF solutions. A potential role for this additive in enhancing rates and yields of 1,4-, as well as 1,2-additions, is suggested.