S-(-)-1-苯基-4-甲基戊-1-醇 | 89537-67-7

• 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: S-(-)-1-苯基-4-甲基戊-1-醇
• 英文名称: S-(-)-1-Phenyl-4-methylpentan-1-ol
• 英文别名: (S)-(-)-5-methyl-1-phenylbutanol；4-methyl-1-phenyl-1-pentanol；4-methyl-1-phenylpentan-1-ol；(1S)-4-methyl-1-phenylpentan-1-ol
• CAS: 89537-67-7
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: CQGNELSSDLGEQT-LBPRGKRZSA-N

物化性质

• 沸点：
  248.0±8.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  S-(-)-1-苯基-4-甲基戊-1-醇 在 sodium periodate 、 lithium aluminium tetrahydride 、 四氧化钌 作用下， 生成 4-甲基-1-戊醇
  参考文献：
  名称：

  测定2,3-氘代3-烷基丙醇的对映体组成和绝对构型的方法

  摘要：

  在Eu（fod）3增强的1 H-NMR光谱中对1-苯基-3-烷基丙醇的C-2和C-3上的非对映体亚甲基质子进行了分配，以开发一种普遍适用的方法来确定对映体的组成和其绝对构型2和/或3-氘代的3-烷基丙醇。

  DOI：

  10.1016/s0040-4039(00)88411-7
• 作为产物：
  描述：

  4-methyl-1-phenyl-pentan-1-ol 生成 S-(-)-1-苯基-4-甲基戊-1-醇
  参考文献：
  名称：

  FURUKAWA, JUN;IWASAKI, SHIGEO;OKUDA, SHIGENOBU, TETRAHEDRON LETT., 1983, 24, N 47, 5257-5260

  摘要：

  DOI：

文献信息

• Rhodium complex with unsymmetrical vicinal diamine ligand: excellent catalyst for asymmetric transfer hydrogenation of ketones
  作者：Sudhindra H. Deshpande、Vaishali S. Shende、Savita K. Shingote、Debamitra Chakravarty、Vedavati G. Puranik、Raghunath V. Chaudhari、Ashutosh A. Kelkar

  DOI：10.1039/c5ra08220j

  日期：——

  investigated. The reaction mixture is homogeneous in methanol unlike in water, where substrate and product are insoluble in water and form separate phase, sodium formate being soluble in water. The activity and enantioselectivity obtained for ATH of ketones using [Rh(Cp*)Cl2]2 and unsymmetrical vicinal diamine ligand as catalyst was comparable with the C2 symmetric benchmark ligands like TsDPEN ((1R,2R)-N-(p-tolylsulfonyl)-1

  从便宜的起始原料如去氧麻黄碱合成了新的不对称邻位二胺配体，其胺和磺酰胺基团的区域和立体位置发生系统性变化。已经研究了使用过渡金属配合物和以甲酸钠为氢源的单甲苯磺酸化不对称邻位二胺配体的新衍生物在水中和甲醇中对芳族烷基酮的催化不对称转移加氢（ATH）。以优异的对映选择性（> 95％ee）和[Rh（CP *）Cl 2 ] 2和配体4转化酮（> 95％）获得手性仲醇作为催化剂。与使用水作为溶剂相比，发现使用甲醇作为酮（以甲酸钠为氢源）进行ATH的溶剂时，对映选择性略高，并且发现与所有研究的酮均相符。与在水中不同，反应混合物在甲醇中是均相的，在水中，底物和产物不溶于水并形成分离的相，而甲酸钠则溶于水。的活性和对映选择性使用酮为ATH获得的[Rh（CP *）氯2 ] 2和不对称连位二胺配体作为催化剂是与可比较的C ^ 2点对称基准的配体等TsDPEN（（1 - [R，2 - [R ） - ñ - （p-甲苯基磺酰基）-1
• An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent
  作者：Giovanni Pinna、Maria Cristina Bellucci、Luciana Malpezzi、Laura Pisani、Stefano Superchi、Alessandro Volonterio、Matteo Zanda

  DOI：10.1016/j.tet.2011.05.033

  日期：2011.7

  and α-acetammido benzyl carbanions by means of a two-step sequence involving highly diastereoselective α-C-alkylation with alkyl halides followed by displacement of the sulfinyl residue (which can be recovered and recycled) by a hydroxyl, a chlorine or an acetamido, respectively, under non-oxidative Pummerer conditions. The scope and limits of the method, including a stereoselective version of the

  N-甲基邻氨基甲酰基芳基苄基亚砜可以用作两步序列，包括高度非对映选择性的α-C-烷基化和烷基卤化物，然后用作α-羟基，α-氯和α-乙酰氨基苄基碳负离子的合成等价物。在非氧化Pummerer条件下，分别通过羟基，氯或乙酰氨基置换亚磺酰基残基（可回收和再循环）。详细讨论了该方法的范围和限制，包括反应的立体选择形式以及该方法的机理。
• Enantioselective preparation of sec. Alcohols from aldehydes and dialkyl zinc compounds, generated in situ from Grignard reagents, using substoichiometric amounts of TADDOL-titanates
  作者：Joanna Linda von dem Bussche-Hünnefeld、Dieter Seebach

  DOI：10.1016/0040-4020(92)80023-9

  日期：1992.7

  the Schlenk trick (precipitation of MgX2 from ethereal solutions by the addition of 1,4-dioxane) mixtures of a Grignard reagent RMgX (X = Cl, Br, I) and 0.5 equiv. ZnCl2 in Et2O can be converted to zinc alkyls R2Zn which in turn are added with enantio-selectivities of up to 99 : 1 to aliphatic and aromatic aldehydes in the presence of Ti(OCHMe2)4 and a chiral titanate derived from an α,α,α′,α′-tetraaryl-1

  使用Schlenk技巧（通过添加1,4-二恶烷，从醚溶液中沉淀出MgX 2），将格氏试剂RMgX（X = Cl，Br，I）和0.5当量的混合物。可以将Et 2 O中的ZnCl 2转化为烷基锌R 2 Zn，然后在Ti（OCHMe 2）4和手性钛酸酯的存在下，将脂族和芳族醛的对映选择性高达99：1。由α，α，α'，α'-四芳基-1,3-二氧戊环-4,5-二甲醇（TADDOL）制得。格氏试剂盒也可以使用双键，苯环或缩醛基。比较了不同的TADDOL在这类对映选择性反应中的用途。
• An efficient desulfonylation method mediated by magnesium in ethanol
  作者：Ge Hyeong Lee、Eun Bok Choi、Eun Lee、Chwang Siek Pak

  DOI：10.1016/0040-4039(93)88080-3

  日期：1993.7

  An extremely convenient desulfonylation method of primary, secondary, tertiary alkyl and vinyl phenyl sulfones was developed by using magnesium in ethanol in the presence of catalytic amount of mercuric chloride to give the corresponding alkanes and alkene in almost quantitative yields.

  通过在催化量的氯化汞存在下，在乙醇中使用镁，开发了一种极为方便的伯，仲，叔烷基和乙烯基苯基砜的磺酰化方法，从而以几乎定量的产率得到了相应的烷烃和烯烃。
• Preparation of polyfunctional diorganomercurials and their transmetallation to diorganozincs. Applications to the preparation of optically active secon
  作者：Michael J. Rozema、Duddu Rajagopal、Charles E. Tucker、Paul Knochel

  DOI：10.1016/0022-328x(92)88002-z

  日期：1992.10

  Two new methods of preparation of functionalized diorganomercurials have been developed. The first method involves a substitution reaction of (ICH2)2Hg with zinc-copper reagents FG-RCu(CN)ZnI in THF/DMF at - 60-degrees-C. Functional groups such as an ester, nitrile, ketone, phosphonate, halide, and boronic ester are tolerated in this reaction. The second method involves a reductive transmetallation between polyfunctional organozinc halides and mercurous chloride (Hg2Cl2). This very convenient procedure provides a rapid route to various functionalized diorganomercurials in good yields (61-89% yield). The synthetic utility of these mercury organometallics is demonstrated. Their transmetallation with zinc dust (toluene, 80-degrees-C, 3-5 h) affords dialkylzincs which add enantioselectively to aldehydes in the presence of a catalytic amount (20 mol%) of the norephedrine derivative 13. This transmetallation can also be used to prepare stereoselectively (E)-alkenylzinc halides (> 98% E). Addition of Cl(H)ZrCp2 to (E)-5-chloropentenylzinc bromide in CH2Cl2 (25-degrees-C, 1 min) affords a 1,1-bimetallic of zinc and zirconium Cl(CH2)4CH(ZnBr)ZrCp2(Cl) which reacts stereoselectively with an aldehyde providing the (E)-disubstituted olefin (49% yield; 100% E).