(3S)-3-甲基-3-对甲苯基-4-戊烯醛 | 105556-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (3S)-3-甲基-3-对甲苯基-4-戊烯醛
• 英文名称: (3S)-3-methyl-3-p-tolyl-4-pentenal
• 英文别名: (3S)-3-methyl-3-(4-methylphenyl)pent-4-enal
• CAS: 105556-94-3
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: JIYIYTSYZPOZGJ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S)-3-甲基-3-对甲苯基-4-戊烯醛 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-4-methyl-4-(p-tolyl)hex-5-enal
  参考文献：
  名称：

  Asymmetric construction of quaternary carbons from chiral malonates : Total syntheses of (+)-epilaurene and (−)-Isolaurene.

  摘要：

  Enantiomerically pure (+)-epilaurene and (-)-isolaurene were obtained from the chiral malonic acid ester (R)-(+)-4, via the 4-methyl-4-p-tolylhex-5-en-1-al (S)-9 prepared by double Wittig reaction under sonication, which underwent subsequent radical induced cyclization.

  DOI：

  10.1016/s0957-4166(00)86009-7
• 作为产物：
  描述：

  (R)-(+)-methyl 3-hydroxy-2-methyl-2-(4-methylphenyl)propionate 在 盐酸 、 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3S)-3-甲基-3-对甲苯基-4-戊烯醛
  参考文献：
  名称：

  Asymmetric construction of quaternary carbons from chiral malonates : Total syntheses of (+)-epilaurene and (−)-Isolaurene.

  摘要：

  Enantiomerically pure (+)-epilaurene and (-)-isolaurene were obtained from the chiral malonic acid ester (R)-(+)-4, via the 4-methyl-4-p-tolylhex-5-en-1-al (S)-9 prepared by double Wittig reaction under sonication, which underwent subsequent radical induced cyclization.

  DOI：

  10.1016/s0957-4166(00)86009-7

文献信息

• Synthetic approach to (-)-cuparenone by rhodium-catalyzed cyclization.
  作者：TETSUJI KAMETANI、KUNIAKI KAWAMURA、MASAYOSHI TSUBUKI、TOSHIO HONDA

  DOI：10.1248/cpb.33.4821

  日期：——

  (-)-α-Cuparenone, (17) was synthesized from the olefinic aldehyde (9) by utilizing a rhodium-catalyzed cyclization as a key step. The optically active aldehyde (7) was prepared by employing an asymmetric [2, 3] sigmatropic rearrangement of a quaternary L-prolinol derivative. The aldehyde (7) was also converted into its antipodal form (24) in several steps.

  (-)-α-Cuparenone (17) 是利用铑催化环化作为关键步骤，从烯烃醛 (9) 合成而来。光学活性醛（7）是通过对一种季L-脯氨醇衍生物进行不对称[2，3]西格玛托普重排而制备的。醛 (7) 还可通过几个步骤转化为其反式 (24)。
• Asymmetric construction of quaternary carbons from chiral malonates : Total syntheses of (+)-epilaurene and (−)-Isolaurene.
  作者：Antoine Fadel、Jean-Louis Canet、Jacques Salaün

  DOI：10.1016/s0957-4166(00)86009-7

  日期：1993.1

  Enantiomerically pure (+)-epilaurene and (-)-isolaurene were obtained from the chiral malonic acid ester (R)-(+)-4, via the 4-methyl-4-p-tolylhex-5-en-1-al (S)-9 prepared by double Wittig reaction under sonication, which underwent subsequent radical induced cyclization.