(R)-3-(2,5-dimethoxy-4-methylphenyl)butanoic acid | 528606-20-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (R)-3-(2,5-dimethoxy-4-methylphenyl)butanoic acid
• 英文别名: (3R)-3-(2,5-dimethoxy-4-methylphenyl)butanoic acid
• CAS: 528606-20-4
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: HWMZXXVLNRCMBB-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-(2,5-dimethoxy-4-methylphenyl)butanoic acid 在 Pd(Ph₃P)6 、 ruthenium(IV) dichloride catalyst potassium tert-butylate 、 三溴化硼 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (R,Z)-8-(methoxymethoxy)-2,2,6,9-tetramethyl-5,6-dihydro-2H-benzo[b]oxocine
  参考文献：
  名称：

  （-）-heliannuol A的对映选择性全合成。

  摘要：

  （-）-helennuol A的有效和对映体控制的总合成已通过采用闭环易位，环氧化物环的连续非对映选择性环氧化和区域选择性还原性裂解来实现。

  DOI：

  10.1039/b211227b
• 作为产物：
  描述：

  (3R)-3-(2,5-dimethoxy-4-methylphenyl)butanenitrile 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以97%的产率得到(R)-3-(2,5-dimethoxy-4-methylphenyl)butanoic acid
  参考文献：
  名称：

  （-）-heliannuol A的对映选择性全合成。

  摘要：

  （-）-helennuol A的有效和对映体控制的总合成已通过采用闭环易位，环氧化物环的连续非对映选择性环氧化和区域选择性还原性裂解来实现。

  DOI：

  10.1039/b211227b

文献信息

• Highly Enantioselective Iridium-Catalyzed Hydrogenation of α,β-Unsaturated Esters
  作者：Jia-Qi Li、Xu Quan、Pher G. Andersson

  DOI：10.1002/chem.201200907

  日期：2012.8.20

  α,β‐Unsaturated esters have been employed as substrates in iridium‐catalyzed asymmetric hydrogenation. Full conversions and good to excellent enantioselectivities (up to 99 % ee) were obtained for a broad range of substrates with both aromatic‐ and aliphatic substituents on the prochiral carbon. The hydrogenated products are highly useful as building blocks in the synthesis of a variety of natural

  在铱催化的不对称氢化反应中，α，β-不饱和酯已被用作底物。对于在手性碳上同时具有芳族和脂族取代基的多种底物，可实现完全转化和良好至优异的对映选择性（高达99％  ee）。氢化产物在多种天然产物和药物的合成中作为构建基非常有用。
• An efficient total synthesis of (+)-heliannuol D
  作者：Mayu Osaka、Makoto Kanematsu、Masahiro Yoshida、Kozo Shishido

  DOI：10.1016/j.tetasy.2010.08.018

  日期：2010.10

  An efficient total synthesis of (+)-heliannuol D was accomplished in 14 steps and in 12% overall yield by employing a diastereoselective conjugate addition reaction to create a tertiary benzylic stereogenic center and simple assembly of the functionalized oxepane framework by an efficient one-pot transformation procedure as the key steps.

  通过采用非对映选择性共轭加成反应生成叔苄基立体异构中心并通过有效的一锅简单地组装官能化的环氧庚烷骨架，可在14个步骤中以14％的总产率完成（+）-helnunuol D的有效全合成改造程序为关键步骤。
• Enantioselective total synthesis of (–)-heliannuol A
  作者：Hidetoshi Kishuku、Mitsuru Shindo、Kozo Shishido

  DOI：10.1039/b211227b

  日期：2003.1.23

  An efficient and enantiocontrolled total synthesis of (-)-heliannuol A has been accomplished by employing ring closing metathesis and sequential diastereoselective epoxidation and regioselective reductive cleavage of the epoxide ring.

  （-）-helennuol A的有效和对映体控制的总合成已通过采用闭环易位，环氧化物环的连续非对映选择性环氧化和区域选择性还原性裂解来实现。
• 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.