(2S,3S,4R,5S,6E)-3,5-dimethoxy-2,4-dimethyl-7-phenylhept-6-en-1-ol | 307492-71-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S,4R,5S,6E)-3,5-dimethoxy-2,4-dimethyl-7-phenylhept-6-en-1-ol
• 英文别名: 3,5-dimethoxy-2,4-dimethyl-7-phenyl-(2S,3S,4R,5S,6E)-6-hepten-1-ol；(2S,3S,4R,5S,E)-3,5-dimethoxy-2,4-dimethyl-7-phenylhept-6-en-1-ol；(E,2S,3S,4R,5S)-3,5-dimethoxy-2,4-dimethyl-7-phenylhept-6-en-1-ol
• CAS: 307492-71-3
• 化学式: C₁₇H₂₆O₃
• 分子量: 278.392
• InChiKey: PFWXOVRVKFTMFG-JJVAXZJPSA-N

物化性质

• 熔点：
  42-43 °C
• 沸点：
  399.4±42.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S,6E)-3,5-dimethoxy-2,4-dimethyl-7-phenylhept-6-en-1-ol 在 sodium methylate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 ((3S,4R,5S,6S,E)-3,5-Dimethoxy-4,6-dimethyloct-1-en-7-yn-1-yl)benzene
  参考文献：
  名称：

  Step-Economic Synthesis of (+)-Crocacin C: A Concise Crotylboronation/[3,3]-Sigmatropic Rearrangement Approach

  摘要：

  The step-economic total synthesis of (+)-crocacin C has been achieved in 20% yield from commercially available starting materials. This approach requires the isolation of only 8 intermediates and can provide a reliable supply of (+)-crocacin C for the development of new antifungal and crop protection agents.

  DOI：

  10.1021/jo301210f
• 作为产物：
  描述：

  (4R)-4-benzyl-3-[(E,2R,3R,4R,5S)-3,5-dimethoxy-2,4-dimethyl-7-phenylhept-6-enoyl]-1,3-oxazolidin-2-one 在 锂硼氢 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2S,3S,4R,5S,6E)-3,5-dimethoxy-2,4-dimethyl-7-phenylhept-6-en-1-ol
  参考文献：
  名称：

  Total synthesis of (+)-crocacin C

  摘要：

  Two approaches toward the total synthesis of cytotoxic polyketide natural product (+)-crocacin C (1) are described. The first approach, which was ultimately unsuccessful, was replaced altogether with a second that afforded target 1 in 10 linear steps from commercially available Evans' chiral propionimide (5% overall yield). No protecting groups were utilized in the total synthesis of 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.003

文献信息

• Formal synthesis of (+)-crocacin C
  作者：Adele E. Pasqua、Frank D. Ferrari、James J. Crawford、Rodolfo Marquez

  DOI：10.1016/j.tetlet.2012.02.049

  日期：2012.4

  The formal synthesis of (+)-crocacin C is reported. The approach described takes advantage of a highly regioselective epoxide cuprate addition and a diastereoselective Overman rearrangement. The synthesis is practical and amenable to scale up.

  报道了（+）-crocacin C的正式合成。所描述的方法利用了高区域选择性的环氧铜酸盐的添加和非对映选择性的超人重排。该综合是实用的并且可以扩大规模。
• Stereoselective Formal Synthesis of Crocacin C via Prins Cyclization
  作者：J. Yadav、M. Reddy、P. Rao、A. Prasad

  DOI：10.1055/s-2007-984896

  日期：——

  A formal synthesis of crocacin C is described proving the versatility of Prins cyclization in natural product synthesis. The ­approach is convergent and highly stereoselective. Cross-metathesis and Heck reactions were utilized for the insertion of an aromatic group in a stereocontrolled manner.

  描述了一种羟基香草酸C的正式合成，证明了Prins环化在天然产物合成中的多样性。该方法是收敛式的，并且具有高度的立体选择性。利用交叉重排和Heck反应以立体控制的方式插入芳香基团。
• Total Synthesis of (+)-Crocacin D
  作者：Luiz C. Dias、Luciana G. de Oliveira、Janaína D. Vilcachagua、Florian Nigsch

  DOI：10.1021/jo047732k

  日期：2005.3.1

  The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.
• Concise Total Synthesis of (+)-Crocacin C
  作者：Gopal Sirasani、Tapas Paul、Rodrigo B. Andrade

  DOI：10.1021/jo800906p

  日期：2008.8.1

  [GRAPHICS]The cytotoxic natural product (+)-crocacin C (1) has been synthesized in 10 linear steps from commercially available Evans' chiral propionimide. in 5% overall yield (8 steps from Evans' chiral dipropionate synthon). No protecting groups were utilized.
• A formal total synthesis of crocacin C
  作者：J.S. Yadav、P. Venkatram Reddy、L. Chandraiah

  DOI：10.1016/j.tetlet.2006.10.141

  日期：2007.1

  An efficient total synthesis of a potent antifungal and moderate cytotoxic agent crocacin C is described. The synthesis involves the generation of four contiguous stereogenic centres via desymmetrization of a meso bicyclic dihydrofuran using asymmetric hydroboration. (c) 2006 Published by Elsevier Ltd.