(R)-trans-1-(1-isopropylbut-2-enyl)-4-methoxybenzene | 675831-37-5

• 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: (R)-trans-1-(1-isopropylbut-2-enyl)-4-methoxybenzene
• CAS: 675831-37-5
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: JGLKHZHDKVFIGC-GJBLVYBDSA-N

物化性质

• 沸点：
  276.9±19.0 °C(Predicted)
• 密度：
  0.914±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R)-trans-1-(1-isopropylbut-2-enyl)-4-methoxybenzene 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 三氯化铝 、 氯化亚砜 、 三苯基膦 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 20.5h， 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 吡啶 、 Burkholderia cepacia lipase 、 氢氧化钾 、 lithium aluminium tetrahydride 、 丙酸 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 51.5h， 生成 (R)-trans-1-(1-isopropylbut-2-enyl)-4-methoxybenzene
  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 reductive allylic alkylation enabled by dual photoredox/palladium catalysis
  作者：Sheng Tang、Hong-Hao Zhang、Shouyun Yu

  DOI：10.1039/d2cc06705f

  日期：——

  A dual photoredox/palladium catalyzed regio- and enantioselective reductive cross-coupling of allylic acetates with tertiary/secondary alkyl bromides has been achieved, and Hantzsch ester is used as a homogeneous organic reductant. This straightforward protocol enables the stereoselective construction of C(sp3)–C(sp3) bonds under mild reaction conditions. Mechanistic studies suggest that this reaction

  已经实现了烯丙基乙酸酯与叔/仲烷基溴化物的双重光氧化还原/钯催化区域和对映选择性还原交叉偶联，并且使用 Hantzsch 酯作为均相有机还原剂。这个简单的协议能够在温和的反应条件下立体选择性构建 C(sp 3 )–C(sp 3 ) 键。机理研究表明，该反应涉及自由基途径，手性 Pd 络合物能够控制区域选择性和对映选择性。
• 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.