(E)-ethyl 3-((4R,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)acrylate | 191277-77-7

• 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: (E)-ethyl 3-((4R,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)acrylate
• 英文别名: ethyl (E)-3-[(4R,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 191277-77-7
• 化学式: C₁₅H₂₆O₄
• 分子量: 270.369
• InChiKey: IXZYYILEEOJNTD-HRFIDBLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-((4R,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)acrylate 在 manganese(IV) oxide 、 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 26.0h， 生成 (E,4R,5R)-4,5-isopropylidenedioxydec-2-enal
  参考文献：
  名称：

  Synthesis of all four isomers of (E)-4,5-dihydroxydec-2-enal using osmium-catalysed asymmetric dihydroxylation

  摘要：

  The enantioselective synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product formed in peroxidised liver microsomal lipids, is accomplished via a Sharpless AD reaction alone or associated as appropriate with a regioselective epimerisation of one of the introduced hydroxy groups. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00125-0
• 作为产物：
  描述：

  反-2-辛烯醛 在 sodium disulfite 、 甲基磺酰胺 、 AD-mix-β 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 80.5h， 生成 (E)-ethyl 3-((4R,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)acrylate
  参考文献：
  名称：

  Synthesis of all four isomers of (E)-4,5-dihydroxydec-2-enal using osmium-catalysed asymmetric dihydroxylation

  摘要：

  The enantioselective synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product formed in peroxidised liver microsomal lipids, is accomplished via a Sharpless AD reaction alone or associated as appropriate with a regioselective epimerisation of one of the introduced hydroxy groups. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00125-0

文献信息

• Chiron approach from D-mannitol to access a diastereomer of the reported structure of an acetogenin, an amide alkaloid and a sex pheromone
  作者：Sandip Chatterjee、Avrajit Manna、Ipsita Chakraborty、Tanurima Bhaumik

  DOI：10.1016/j.carres.2018.12.008

  日期：2019.2

  employed successfully to access two different natural products bearing two contiguous stereogenic centers. As a result, first chiron approach to formal total synthesis of an amide alkaloid, (4R,5R,2E)-4,5-dihydroxy-1-(piperidin-1-yl)dec-2-en-1-one and total synthesis of a male sex pheromone in parasitic Hymenoptera, (4R,5R)-(-)-5-hydroxy-4-decanolide have also been achieved.

  （3R，4S，5R）-（-）-3,5-dihydroxy-4-decanolide的一种简短，简单且方便的Chiron方法，已报道的天然产乙酸原素（（+）-polyporolide）结构的迄今未知的非对映异构体从市售的廉价手性池分子D-（+）-甘露醇开始，已在九个有效步骤中完成了本发明。为此目的，由D-（+）-甘露醇分6步合成的高级中间体被成功地用于获得带有两个连续立体中心的两种不同天然产物。结果，第一种凯隆方法正式合成了酰胺生物碱，（4R，5R，2E）-4,5-二羟基-1-（哌啶-1-基）癸-2-烯-1-酮和总（4R，5R）-（-）-5-羟基-4-癸醇化物的寄生性膜翅目中雄性信息素的合成也已实现。
• Synthesis of all four isomers of (E)-4,5-dihydroxydec-2-enal using osmium-catalysed asymmetric dihydroxylation
  作者：Pietro Allevi、Giorgio Tarocco、Alessandra Longo、Mario Anastasia、Francesco Cajone

  DOI：10.1016/s0957-4166(97)00125-0

  日期：1997.4

  The enantioselective synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product formed in peroxidised liver microsomal lipids, is accomplished via a Sharpless AD reaction alone or associated as appropriate with a regioselective epimerisation of one of the introduced hydroxy groups. (C) 1997 Elsevier Science Ltd.