(S)-4-(4-Methoxy-benzyloxy)-dihydro-furan-2-one | 161772-32-3

• 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: (S)-4-(4-Methoxy-benzyloxy)-dihydro-furan-2-one
• CAS: 161772-32-3
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: JMEJRZPYFQCFLG-NSHDSACASA-N

物化性质

• 沸点：
  388.1±37.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-4-(4-Methoxy-benzyloxy)-dihydro-furan-2-one 在 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 乙酰氯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (Z)-(S)-9-Hydroxy-8-(4-methoxy-benzyloxy)-non-5-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis and X-ray crystallographic structure of the right-hand hemisphere of halicholactone and neohalicholactone

  摘要：

  报道了海洋天然产物哈利醇内酯和新哈利醇内酯的右半球的合成及其X射线晶体结构，该结构包含一个九元内酯环和一个环丙烷环。

  DOI：

  10.1039/c39950000139
• 作为产物：
  描述：

  2,2,2-三氯代亚氨逐乙酸-4-甲氧基苄酯 、 (S)-(-)-β-羟基-γ-丁内酯 在 三氟甲磺酸 作用下， 以73%的产率得到(S)-4-(4-Methoxy-benzyloxy)-dihydro-furan-2-one
  参考文献：
  名称：

  Synthesis and X-ray crystallographic structure of the right-hand hemisphere of halicholactone and neohalicholactone

  摘要：

  报道了海洋天然产物哈利醇内酯和新哈利醇内酯的右半球的合成及其X射线晶体结构，该结构包含一个九元内酯环和一个环丙烷环。

  DOI：

  10.1039/c39950000139

文献信息

• Synthetic studies toward the microtubule-stabilizing agent laulimalide: synthesis of the C15–C28 fragment
  作者：B.Travis Messenger、Bradley S Davidson

  DOI：10.1016/s0040-4039(00)02115-8

  日期：2001.1

  The C15–C28 fragment of the paclitaxel-like antimicrotubule agent laulimalide has been synthesized in 12 linear steps with an overall yield of 14%. The methyldihydropyran ring of the side chain was efficiently prepared using ring-closing olefin metathesis chemistry and the 19,20-syn-diol was generated through the addition of a mixed vinyl zincate to a protected α-hydroxyaldehyde.

  紫杉醇样抗微管药laulimalide的C 15 –C 28片段已通过12个线性步骤合成，总产率为14％。使用闭环烯烃复分解化学有效地制备了侧链的甲基二氢吡喃环，并且通过将混合的乙烯基锌酸酯添加至受保护的α-羟基醛中来生成19,20-顺式-二醇。
• Total Synthesis of Halicholactone and Neohalicholactone¹
  作者：Douglas J. Critcher、Stephen Connolly、Martin Wills

  DOI：10.1021/jo962312j

  日期：1997.9.1

  The total synthesis of the marine natural products neohalicholactone (1) and halicholactone (2), in enantiomerically pure form, are reported. Key steps in the synthesis of each compound include a cis-selective Wittig reaction, stereoselective cyclopropanation, nine-membered lactone formation using the Yamaguchi method and late-stage stereoselective Cr(II)/Ni(II) mediated coupling of vinyl iodides 39 and 50 with aldehyde 14. In the case of the neohalicholactone synthesis the two major components which were coupled in this convergent synthesis were each derived from the enantiomers of commercially available malic acid. The synthesis served to confirm the original assignment of absolute configuration which was made by Yamada and Clardy. We also demonstrated, through the preparation of diastereoisomers, that another reported compound closely related to neohalicholactone is likely to be the C-15 epimer 67.