3-羟基-3-(萘基-(1))-戊烷 | 3099-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-羟基-3-(萘基-(1))-戊烷
• 英文名称: 3-(naphthalen-1-yl)pentan-3-ol
• 英文别名: 3-hydroxy-3-(naphthyl-(1))-pentane；1-(1-Hydroxy-1-aethyl-propyl)-naphthalin；3-Hydroxy-3-(naphthyl-(1))-pentan；3-naphthalen-1-ylpentan-3-ol
• CAS: 3099-68-1
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: FZKIKZPHWVBODD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3-羟基-3-(萘基-(1))-戊烷 在 potassium hydrogensulfate 作用下， 生成 3-(1-Naphthyl)-penten-(2)
  参考文献：
  名称：

  Salkind; Soniss, Zhurnal Obshchei Khimii, 1936, vol. 6, p. 988,995

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴代萘 、 3-戊酮 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以73%的产率得到3-羟基-3-(萘基-(1))-戊烷
  参考文献：
  名称：

  三光气和DMAP作为叔醇化学选择性脱水的温和试剂

  摘要：

  据报道，三光气和DMAP作为温和试剂用于叔醇的化学选择性脱水。该反应在室温下在二氯甲烷中进行，很容易被宽范围的底物所耐受，优先以（E）-几何结构产生烯烃。尽管通常优选霍夫曼产物的形成，但是当反应在二氯乙烷中在回流下进行时，观察到烯烃对Zaitzev产物的选择性的急剧变化。

  DOI：

  10.1021/acs.orglett.9b01959

文献信息

• Conformational Studies by Dynamic Nuclear Magnetic Resonance. 59.¹ Stereodynamics of Conformational Enantiomers in the Atropisomers of Hindered Naphthylcarbinols
  作者：Daniele Casarini、Lodovico Lunazzi、Andrea Mazzanti

  DOI：10.1021/jo970113+

  日期：1997.5.1

  Naphthyldialkylmethanols ArRR'COH (Ar = 1-naphthyl or 1-naphthyl-2-methyl) exist as a pair of atropisomers created by the restricted rotation about the Ar-COH bond. They can be detected by low-temperature NMR spectroscopy but can also be separated as stable compounds at room temperature if both the alkyl substituents are bulky tert-butyl groups (one such example is provided by compound 1, R = R' = Bu(t) with Ar = 1-naphthyl)

  萘二烷基甲醇ArRR'COH（Ar = 1-萘基或1-萘基-2-甲基）以一对阻转异构体的形式存在，这些阻转异构体是由围绕Ar-COH键的受限旋转产生的。它们可以通过低温NMR光谱进行检测，但是如果两个烷基取代基均为大的叔丁基，则它们也可以在室温下作为稳定的化合物分离（一个这样的例子由化合物1提供，R = R'= Bu（t ），其中Ar = 1-萘基）。发现这些阻转异构体相互转化的活化自由能（DeltaG（））在7.6 kcal mol（-）（1）之间变化（如7中，R = R'= Me，Ar = 1-萘基-2-甲基）和32.9 kcal mol（-）（1）（与1相同）。通过差值NOE实验或利用在两种阻转异构体中相差很大的H-8化学位移来分配正周平面（sp）或反周平面（ap）结构。取决于取代基，在平衡处更稳定的物质可以是sp或ap阻转异构体。当R = R'= Pr（i）且R = R'= Et（如果Ar
• A Short Access to Symmetrically α,α-Disubstituted α-Amino Acids from Acyl Cyanohydrins
  作者：Philippe Bertus、Fatma Boukattaya、Julien Caillé、Houcine Ammar、Florian Rouzier、Fabien Boeda、Morwenna Pearson-Long

  DOI：10.1055/s-0035-1560404

  日期：——

  including the particularly simple divinylglycine, which is not easily accessible by using conventional methods. A straightforward synthesis of symmetrically α,α-disubstituted α-amino acids is presented. The key step of this process relies on the efficient double addition of Grignard reagents to acyl cyanohydrins to provide N-acyl amino alcohols selectively in good yields. The chemoselectivity of the reaction

  摘要 提出了对称的α，α-二取代的α-氨基酸的直接合成。该方法的关键步骤依赖于将格氏试剂有效地双重添加到酰基氰醇中，以高产率选择性地提供N-酰基氨基醇。反应的化学选择性受酰基部分的性质调节。制备了11种氨基酸，包括特别简单的二乙烯基甘氨酸，使用常规方法不易获得。 提出了对称的α，α-二取代的α-氨基酸的直接合成。该方法的关键步骤依赖于将格氏试剂有效地双重添加到酰基氰醇中，以高产率选择性地提供N-酰基氨基醇。反应的化学选择性受酰基部分的性质调节。制备了11种氨基酸，包括特别简单的二乙烯基甘氨酸，使用常规方法不易获得。
• Conformational Studies by Dynamic NMR. 64.¹ Stereomutations of Atropisomers and of Conformational Enantiomers in Ethers of Hindered Naphthylcarbinols
  作者：Daniele Casarini、Lodovico Lunazzi、Andrea Mazzanti、Elisabetta Foresti

  DOI：10.1021/jo9804801

  日期：1998.7.1

  Methyl or ethyl ethers of 1-naphthyl carbinols ArCR2OR' (Ar = 1-naphthyl, R' = Me, Et) can occur in a range of rotational conformations whose population varies with the nature of the substituents R. The passage between such conformation minima is achieved by rotation, during which one group R or OR' passes either the 2- or the 8-position of the naphthalene, and depending on the nature of R and OR', some of these interconversions are slow on the NMR time scale. Dynamic NMR experiments, supported by molecular mechanics calculations, show that different minima are preferred as the R group changes. These conformations are identified, their populations are determined, and the barriers to their interconversions are measured. In particular when R is a tert-butyl group, two atropisomers (with the OMe moiety near the 2- or 8-position) could be physically separated and their structures determined by NOE experiments in solution and X-ray diffraction in the solid state. Each of these exists as a pair of stereolabile enantiomers, with a barrier of 9-10 kcal mol(-1) for interconversion.
• Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols
  作者：Moshood O. Ganiu、Alexander H. Cleveland、Jarrod L. Paul、Rendy Kartika

  DOI：10.1021/acs.orglett.9b01959

  日期：2019.7.19

  The utility of triphosgene and DMAP as mild reagents for chemoselective dehydration of tertiary alcohols is reported. Performed in dichloromethane at room temperature, this reaction is readily tolerated by a broad scope of substrates, yielding alkenes preferentially with the (E)-geometry. While formation of the Hofmann products is generally favored, a dramatic change in alkene selectivity toward the

  据报道，三光气和DMAP作为温和试剂用于叔醇的化学选择性脱水。该反应在室温下在二氯甲烷中进行，很容易被宽范围的底物所耐受，优先以（E）-几何结构产生烯烃。尽管通常优选霍夫曼产物的形成，但是当反应在二氯乙烷中在回流下进行时，观察到烯烃对Zaitzev产物的选择性的急剧变化。
• Salkind; Soniss, Zhurnal Obshchei Khimii, 1936, vol. 6, p. 988,995
  作者：Salkind、Soniss

  DOI：——

  日期：——