(3R)-trans-3-(4-methoxyphenyl)-2-methylhex-4-enoic acid | 675831-36-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (3R)-trans-3-(4-methoxyphenyl)-2-methylhex-4-enoic acid
• 英文别名: (E,3S)-3-(4-methoxyphenyl)-2-methylhex-4-enoic acid
• CAS: 675831-36-4
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: SZXHXGOTIPUUSG-XPVSQNCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R)-trans-3-(4-methoxyphenyl)-2-methylhex-4-enoic acid 在 吡啶 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 三氯化铝 、 氯化亚砜 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 39.0h， 生成 (4S)-3,4-dihydro-4-(1-methylethyl)-7-methoxy-2H-naphthalen-1-one
  参考文献：
  名称：

  Enantioselective synthesis of cis-7-methoxy-calamenene via Claisen rearrangement of an enzymatically resolved allyl alcohol

  摘要：

  An enantioselective synthesis of cis-7-methoxy-calamenene 1 has been accomplished through the following key-steps: (i) enzymatic resolution of the racemic allyl alcohol 3 to furnish the (R)-enantiomer (ee >99%); (ii) Claisen-orthoester rearrangement of 4 to introduce the isopropyl unit on the benzylic position (99% ee); (iii) diastereoselective reduction of dihydronaphthalene derivative 11 to give the cis-isomer 12 (98% de); (iv) regioselective introduction of the formyl group by a Vilsmeier reaction followed by reduction to give 1. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.021
• 作为产物：
  描述：

  (E)-1-(4-methoxyphenyl)pent-1-en-3-ol 在 Burkholderia cepacia lipase 、 氢氧化钾 、 丙酸 作用下， 以 乙醇 、 水 为溶剂， 反应 33.0h， 生成 (3R)-trans-3-(4-methoxyphenyl)-2-methylhex-4-enoic acid
  参考文献：
  名称：

  Enantioselective synthesis of cis-7-methoxy-calamenene via Claisen rearrangement of an enzymatically resolved allyl alcohol

  摘要：

  An enantioselective synthesis of cis-7-methoxy-calamenene 1 has been accomplished through the following key-steps: (i) enzymatic resolution of the racemic allyl alcohol 3 to furnish the (R)-enantiomer (ee >99%); (ii) Claisen-orthoester rearrangement of 4 to introduce the isopropyl unit on the benzylic position (99% ee); (iii) diastereoselective reduction of dihydronaphthalene derivative 11 to give the cis-isomer 12 (98% de); (iv) regioselective introduction of the formyl group by a Vilsmeier reaction followed by reduction to give 1. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.021

文献信息

• Enantioselective synthesis of cis-7-methoxy-calamenene via Claisen rearrangement of an enzymatically resolved allyl alcohol
  作者：Elisabetta Brenna、Claudia Dei Negri、Claudio Fuganti、Francesco G. Gatti、Stefano Serra

  DOI：10.1016/j.tetasy.2003.11.021

  日期：2004.1

  An enantioselective synthesis of cis-7-methoxy-calamenene 1 has been accomplished through the following key-steps: (i) enzymatic resolution of the racemic allyl alcohol 3 to furnish the (R)-enantiomer (ee >99%); (ii) Claisen-orthoester rearrangement of 4 to introduce the isopropyl unit on the benzylic position (99% ee); (iii) diastereoselective reduction of dihydronaphthalene derivative 11 to give the cis-isomer 12 (98% de); (iv) regioselective introduction of the formyl group by a Vilsmeier reaction followed by reduction to give 1. (C) 2003 Elsevier Ltd. All rights reserved.