(6S,2E)-6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl phenylcarbamate | 122313-77-3

• 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: (6S,2E)-6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl phenylcarbamate
• 英文别名: (6S)-6,7-Dihydroxygeranylphenylcarbamate；(6S)-(-)-6,7-dihydroxygeranyl N-phenylcarbamate；[(E,6S)-6,7-dihydroxy-3,7-dimethyloct-2-enyl] N-phenylcarbamate
• CAS: 122313-77-3
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: BJSMCYVUDVXIGH-FQNOHDAGSA-N

物化性质

• 熔点：
  98-99 °C(Solv: benzene (71-43-2))
• 沸点：
  440.1±45.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6S,2E)-6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl phenylcarbamate 在 吡啶 、 lithium aluminium tetrahydride 、 四氯化锡 作用下， 生成 2H-吡喃-3-醇,6-乙烯基四氢-2,2,6-三甲基-,(3S,6R)-
  参考文献：
  名称：

  Verbena × hybridaflower volatiles attractive to Western flower thrips,Frankliniella occidentalis

  摘要：

  DOI：

  10.1002/(sici)1096-9063(199906)55:6<660::aid-ps2>3.0.co;2-v
• 作为产物：
  描述：

  (E)-3,7-dimethylocta-2,6-dien-1-yl phenylcarbamate 以 乙醇 、 水 为溶剂， 反应 48.0h， 以49%的产率得到(6S,2E)-6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl phenylcarbamate
  参考文献：
  名称：

  Microbial transformations. 12. Regiospecific and asymmetric oxidation of the remote double bond of geraniol

  摘要：

  DOI：

  10.1021/jo00280a043

文献信息

• Synthesis of All Four Stereoisomers of Enantiomerically Pure Tetrahydro-2,2,6-trimethyl-6-vinyl-2<i>H</i>-pyran-3-ols
  作者：A. Méou、N. Bouanah、A. Archelas、X. M. Zhang、R. Guglielmetti、R. Furstoss

  DOI：10.1055/s-1991-26542

  日期：——

  The four enantiomerically pure title compounds were prepared in three steps and good yield from (6S)- or (6R)-6,7-dihydroxygeranyl N-phenylcarbamate.

  以(6S)-或(6R)-6,7-二羟基苯乙酰基 N-苯基氨基甲酸酯为原料，分三步制备出了四种对映体纯度很高的标题化合物。
• Synthesis of All Four Stereoisomers of Enantiomerically Pure<i>cis</i>- and<i>trans</i>-Linalyl Oxides
  作者：A. Méou、N. Bouanah、A. Archelas、X. M. Zhang、R. Guglielmetti、R. Furstoss

  DOI：10.1055/s-1990-27003

  日期：——

  The four enantiomerically pure cis- and trans-linalyl oxides can be prepared in one step and good yield from (6S)- or (6R)-6,7-dihydroxygeranyl phenylcarbamate.

  以 (6S)- 或 (6R)-6,7- 二羟基苯丙氨酰苯基氨基甲酸酯为原料，可一步制备出四种对映体纯度较高的顺式和反式芳樟基氧化物。
• Microbial transformationsd. 19. Asymmetric dihydroxylation of the remote double bond of geraniol: a unique stereochemical control allowing easy access to both enantiomers of geraniol-6,7-diol
  作者：X. M. Zhang、A. Archelas、R. Furstoss

  DOI：10.1021/jo00012a010

  日期：1991.6

  The microbiological oxygenation of the geraniol N-phenylcarbamate 1 by Aspergillus niger is described, which leads regiospecifically to a formal dihydroxylation of its C(6) = C(7) double bond. By use of different pH values of the incubation medium, it is possible to modulate the stereochemical outcome of this reaction. Thus, 6S diol 3 (ee > 95%) is obtained at pH 2, whereas 6R diol 3 (ee > 95%) is formed at pH 6-7. The mechanism of this reaction has been studied by (O2)-O-18 labeling. It was shown that, in a first step, the 6S epoxide 2 is almost exclusively formed. The second step involves hydrolysis of this key intermediate via a spontaneous acid-catalyzed hydrolysis at pH 2 or an enzymatic hydrolysis at pH 6-7.
• FOURNERON, J. D.;ARCHELAS, A.;FURSTOES, R., J. ORG. CHEM., 54,(1989) N9, C. 4686-4688
  作者：FOURNERON, J. D.、ARCHELAS, A.、FURSTOES, R.

  DOI：——

  日期：——
• MEOU, A.;BOUANAH, N.;ARCHELAS, A.;ZHANG, X. M.;GUGLIELMETTI, R.;FURSTOSS,+, SYNTHESIS,(1990) N, C. 752-753
  作者：MEOU, A.、BOUANAH, N.、ARCHELAS, A.、ZHANG, X. M.、GUGLIELMETTI, R.、FURSTOSS,+

  DOI：——

  日期：——