methyl (R)-(-)-4-(4-methoxyphenyl)-4-methylhex-5-enoate | 235101-23-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl (R)-(-)-4-(4-methoxyphenyl)-4-methylhex-5-enoate
• 英文别名: methyl (4R)-4-(4-methoxyphenyl)-4-methylhex-5-enoate
• CAS: 235101-23-2
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: CHLGVYOLQUTSAL-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (R)-(-)-4-(4-methoxyphenyl)-4-methylhex-5-enoate 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 (R)-(-)-3,7-dimethyl-3-(4-methoxyphenyl)octa-1,6-diene
  参考文献：
  名称：

  Total synthesis of (−)-sporochnol A, the fish deterrent, from a chiral malonate

  摘要：

  From a single chiron, the homochiral benzylic malonic acid ester (R)-(+)-2 available with high enantiomeric excess by enzymatic hydrolysis (PLE acetonic powder), enantiomerically pure (-)-sporochnol A 1 was prepared. This versatile method allows preparation of sporochnol 1, via aldehydes 7 and 15, in good overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00086-5
• 作为产物：
  描述：

  (R)-(+)-3-(methoxymethoxy)-2-(4-methoxyphenyl)-2-methylpropanol 在 盐酸 、 正丁基锂 、 戴斯-马丁氧化剂 、 magnesium 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 65.0h， 生成 methyl (R)-(-)-4-(4-methoxyphenyl)-4-methylhex-5-enoate
  参考文献：
  名称：

  Total synthesis of (−)-sporochnol A, the fish deterrent, from a chiral malonate

  摘要：

  From a single chiron, the homochiral benzylic malonic acid ester (R)-(+)-2 available with high enantiomeric excess by enzymatic hydrolysis (PLE acetonic powder), enantiomerically pure (-)-sporochnol A 1 was prepared. This versatile method allows preparation of sporochnol 1, via aldehydes 7 and 15, in good overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00086-5

文献信息

• A New Powerful Strategy for the Organocatalytic Asymmetric Construction of a Quaternary Carbon Stereogenic Center
  作者：Yogo Inokoishi、Niiha Sasakura、Keiji Nakano、Yoshiyasu Ichikawa、Hiyoshizo Kotsuki

  DOI：10.1021/ol100350w

  日期：2010.4.2

  A new method for chiral diamine-catalyzed Robinson-type annulation was developed to construct cyclohexenone derivatives bearing a quaternary carbon stereogenic center at the 4-position in high enantiomeric excess. This method was successfully applied to the short synthesis of (+)-sporochnol A.

  开发了一种新的手性二胺催化的罗宾逊型环化的新方法，以构建在高对映体过量的4位带有季碳立构中心的环己烯酮衍生物。该方法已成功应用于（+）-孢子醇A的短合成。
• Total synthesis of (−)-sporochnol A, the fish deterrent, from a chiral malonate
  作者：Antoine Fadel、Lucie Vandromme

  DOI：10.1016/s0957-4166(99)00086-5

  日期：1999.3

  From a single chiron, the homochiral benzylic malonic acid ester (R)-(+)-2 available with high enantiomeric excess by enzymatic hydrolysis (PLE acetonic powder), enantiomerically pure (-)-sporochnol A 1 was prepared. This versatile method allows preparation of sporochnol 1, via aldehydes 7 and 15, in good overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.