(S)-4,4-dimethyl-3-phenylpentan-1-ol | 137542-89-3

• 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: (S)-4,4-dimethyl-3-phenylpentan-1-ol
• 英文别名: (S)-(-)-4,4-dimethyl-3-phenyl-1-pentanol；(3S)-4,4-dimethyl-3-phenylpentan-1-ol
• CAS: 137542-89-3
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: ORMQZBOTAIGXCE-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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

• 作为反应物：
  描述：

  (S)-(-)-α-甲氧基-α-(三氟甲基)苯乙酸 、 (S)-4,4-dimethyl-3-phenylpentan-1-ol 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-4,4-dimethyl-3-phenyl-pentyl ester
  参考文献：
  名称：

  Asymmetric Michael additions to .alpha.,.beta.-unsaturated oxazolines. An efficient preparation of chiral .beta.,.beta.-disubstituted propionaldehydes

  摘要：

  A short stereoselective route to a variety of chiral, nonracemic alpha,beta-unsaturated oxazolines derived from (S)-tert-leucinol is described. Addition of organolithium reagents to this chiral oxazoline occurs in a Michael fashion, giving rise to adducts with high diastereoselectivity. Reductive cleavage of the oxazoline leaves the beta,beta-disubstituted aldehydes in > 93% ee. This process represents a significant improvement in one of the earliest asymmetric conjugate additions first reported in 1975.

  DOI：

  10.1021/jo00025a027
• 作为产物：
  描述：

  E-(+)-(1'S,2'S)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-3-phenylprop-2-enamide 在 正丁基锂 、 ammonia borane 、 二异丙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 (S)-4,4-dimethyl-3-phenylpentan-1-ol
  参考文献：
  名称：

  （S，S）-（+）-伪麻黄碱作为不对称共轭加成和串联共轭加成/α-烷基化反应中的手性助剂

  摘要：

  有机锂试剂对（S，S）-（+）-伪麻黄碱酰胺进行高度的区域和非对映选择性1,4-加成，从而以优异的收率和非对映选择性提供相应的β-烷基取代的加合物。另外，在共轭加成步骤之后产生的中间烯醇锂经历高度非对映选择性烷基化反应，以高收率提供α，β-二烷基取代的酰胺。使用非常简单和高产率的方法，将获得的加合物转化为手性非外消旋的β-烷基和α，β-二烷基取代的羧酸以及γ-烷基和β，γ-二烷基取代的醇。

  DOI：

  10.1021/jo061205e

文献信息

• Copper-Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Aryl- and Alkenylboronates
  作者：Ryo Shintani、Keishi Takatsu、Momotaro Takeda、Tamio Hayashi

  DOI：10.1002/anie.201103581

  日期：2011.9.5

  The asymmetric allylic substitution of allyl phosphates with aryl‐ and alkenylboronates catalyzed by a copper/N‐heterocyclic carbene complex was developed and the γ‐substitution products were obtained with high enantioselectivity (see scheme). To account for the observed influence of the reaction parameters a possible catalytic cycle for this process was proposed.

  开发了铜/ N-杂环卡宾配合物催化的磷酸烯丙酯被芳基和链烯基硼酸酯的不对称烯丙基取代，并获得了高对映选择性的γ-取代产物（参见方案）。为了考虑观察到的反应参数的影响，提出了该方法可能的催化循环。
• Lipase catalyzed acylation of primary alcohols with remotely located stereogenic centres: the resolution of (±)-4,4-dimethyl-3-phenyl-1-pentanol
  作者：Sunil Sabbani、Erik Hedenström、Jimmy Andersson

  DOI：10.1016/j.tetasy.2007.07.002

  日期：2007.7

  Enantio selective acylation of some(+/-)-3-alkyl-3-phenyl-1-propanols was performed with enzymes as catalysts. Moderate enantiomeric ratios (E), ranging up to E = 11.6, were obtained. In the resolution, some of the lipases selectively acylated the (+)-enantiomer while others acylated the (-)-enantiomer of the gamma-substituted primary alcohols 1-4. Thus, it is possible to obtain both enantiomers of the alcohols as remaining substrate with high enantiomeric purity. The resolution of (+/-)-4,4-dimethyl-3-phenyl-1-pentanol 4 was extensively studied and screening experiments were conducted to select suitable lipase(s), reaction medium, acyl donor and appropriate temperature combinations to increase the enantiomeric ratio. Chirazyme (R) L-6/chloroform/vinyl propionate/38 degrees C and Chirazyme (R) L-7/di-iso-propyl ether/vinyl propionate/0 degrees C were chosen to obtain both enantiomers, (R)-(+)-4 and (S)-(-)-4, respectively, via sequential resolutions in excellent enantiomeric excess (> 98%) and in 25% and 22% yield, respectively. (c) 2007 Elsevier Ltd. All rights reserved.