(2S,3S,4R,5S,E)-2,4-dimethyl-7-phenylhept-6-ene-1,3,5-triol | 849801-01-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (2S,3S,4R,5S,E)-2,4-dimethyl-7-phenylhept-6-ene-1,3,5-triol
• 英文别名: (E,2S,3S,4R,5S)-2,4-dimethyl-7-phenylhept-6-ene-1,3,5-triol
• CAS: 849801-01-0
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: ARKPVCFXAVMRLN-DBMYPJKLSA-N

物化性质

• 沸点：
  455.8±45.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S,E)-2,4-dimethyl-7-phenylhept-6-ene-1,3,5-triol 在 4-甲基苯磺酸吡啶 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 tert-butyldiphenyl((S)-2-((4S,5R,6S)-2,2,5-trimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)propoxy)silane
  参考文献：
  名称：

  Total Synthesis of (+)-Crocacin C

  摘要：

  [GRAPHICS]The total synthesis of (+)-crocacin C is described. The convergent asymmetric synthesis relies on the use of a regio- and diastereoselective epoxidation of an allylic alcohol with m-CPBA followed by epoxide opening with Me2CuCNLi2 and a Stille cross-coupling between E-vinyl stannane 5 and E-vinyl iodide 6 to establish the (E,E)-dienamide moiety.

  DOI：

  10.1021/ol016845c
• 作为产物：
  描述：

  (4R)-4-benzyl-3-[(E,2R,3R,4R,5S)-3,5-dihydroxy-2,4-dimethyl-7-phenylhept-6-enoyl]-1,3-oxazolidin-2-one 在 锂硼氢 作用下， 以 甲醇 为溶剂， 以66%的产率得到(2S,3S,4R,5S,E)-2,4-dimethyl-7-phenylhept-6-ene-1,3,5-triol
  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

• Step-Economic Synthesis of (+)-Crocacin C: A Concise Crotylboronation/[3,3]-Sigmatropic Rearrangement Approach
  作者：Adele E. Pasqua、Frank D. Ferrari、Chris Hamman、Yanzhou Liu、James J. Crawford、Rodolfo Marquez

  DOI：10.1021/jo301210f

  日期：2012.8.17

  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.
• Total Synthesis of (+)-Crocacin C
  作者：Luiz C. Dias、Luciana G. de Oliveira

  DOI：10.1021/ol016845c

  日期：2001.11.1

  [GRAPHICS]The total synthesis of (+)-crocacin C is described. The convergent asymmetric synthesis relies on the use of a regio- and diastereoselective epoxidation of an allylic alcohol with m-CPBA followed by epoxide opening with Me2CuCNLi2 and a Stille cross-coupling between E-vinyl stannane 5 and E-vinyl iodide 6 to establish the (E,E)-dienamide moiety.
• 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.
• Total synthesis of (+)-crocacin C
  作者：Gopal Sirasani、Tapas Paul、Rodrigo B. Andrade

  DOI：10.1016/j.bmc.2010.03.003

  日期：2010.6.1

  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.