(R)-p-cymen-9-yl acetate | 145621-69-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-p-cymen-9-yl acetate
• 英文别名: [(2R)-2-(4-methylphenyl)propyl] acetate
• CAS: 145621-69-8
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: XGKCUFHHSUQBHI-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-p-cymen-9-yl acetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (R)-2-p-tolylpropan-1-ol
  参考文献：
  名称：

  Enzyme catalyzed monohydrolysis of 2-aryl-1 3-propanediol diacetates. A study of structural effects of the aryl moiety on the enantioselectivity

  摘要：

  DOI：

  10.1016/s0040-4020(01)87892-3
• 作为产物：
  描述：

  2-(p-methylphenyl)-1,3-propanediol 在 4-二甲氨基吡啶 sodium hydroxide 、 sodium tetrahydroborate 、 phosphate buffer 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 11.0h， 生成 (R)-p-cymen-9-yl acetate
  参考文献：
  名称：

  Enzyme catalyzed monohydrolysis of 2-aryl-1 3-propanediol diacetates. A study of structural effects of the aryl moiety on the enantioselectivity

  摘要：

  DOI：

  10.1016/s0040-4020(01)87892-3

文献信息

• NHC-Cu-Catalyzed Enantioselective Hydroboration of Acyclic and Exocyclic 1,1-Disubstituted Aryl Alkenes
  作者：Rosa Corberán、Nicholas W. Mszar、Amir H. Hoveyda

  DOI：10.1002/anie.201102398

  日期：2011.7.25

  Tough nut to crack: Chiral bidentate N‐heterocyclic carbene copper complexes were designed that promote enantioselective hydroborations of one of the most difficult substrate classes: acyclic and exocyclic 1,1‐disubstituted alkenes undergo reaction with >98 % site selectivity, in up to >98 % yield and e.r=96.5:3.5 (see scheme, B2(pin)2 = bis(pinacolato)diboron).

  难以破解：手性双齿N-杂环卡宾铜络合物的设计可促进最困难的底物类型之一的对映选择性氢硼化：无环和环外1,1-二取代烯烃以> 98％的位点选择性进行反应，直至>产率为98％，er ＝ 96.5∶3.5（参见方案，B 2（pin）2＝双（频哪醇）二硼）。
• New Monoterpene Glucoside from the Aerial Parts of Thyme (<i>Thymus vulgaris</i>L.)
  作者：Hiroyuki TAKEUCHI、Zhan-Guo LU、Tomoyuki FUJITA

  DOI：10.1271/bbb.68.1131

  日期：2004.1

  A new monoterpene glucoside (1) was isolated from a methanol extract of the dried aerial parts of thyme (Thymus vulgaris L.), together with known 2- and 5-beta-D-glucopyranosylthymoquinols (2 and 3, respectively), and (-)-angelicoidenol-beta-D-glucopyranoside (4). The structure of 1 was elucidated to be (R)-p-cymen-9-yl beta-D-glucopyranoside by spectral evidence and enantioselective synthesis from

  从百里香干燥百里香（Thymus vulgaris L.）的甲醇提取物中分离出一种新的单萜糖苷（1），以及已知的2-和5-β-D-吡喃葡糖基胸腺喹诺醇（分别为2和3），和（ -）-天使烯醇-β-D-吡喃葡萄糖苷（4）。通过光谱证据和从p衍生的（R）-和（S）-p-cymen-9-ol的对映选择性合成，将1的结构阐明为（R）-p-cymen-9-基β-D-吡喃葡萄糖苷。 -cymen-8-ol。
• Lipase-mediated resolution of substituted 2-aryl-propanols: application to the enantioselective synthesis of phenolic sesquiterpenes
  作者：Stefano Serra

  DOI：10.1016/j.tetasy.2011.03.012

  日期：2011.3

  A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished. (C) 2011 Elsevier Ltd. All rights reserved.