(S)-2-羟基-4-亚甲基-5-己烯酸甲酯 | 134393-17-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (S)-2-羟基-4-亚甲基-5-己烯酸甲酯
• 英文名称: (S)-Methyl 2-Hydroxy-4-methylene-5-hexenoate
• 英文别名: (S)-ethyl 2-hydroxy-4-methylene-5-hexenoate；methyl (2S)-2-hydroxy-4-methylidenehex-5-enoate
• CAS: 134393-17-2
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: SPGYCJULHRZDCX-ZETCQYMHSA-N

物化性质

• 沸点：
  220.8±20.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-2-羟基-4-亚甲基-5-己烯酸甲酯 在 咪唑 、 二异丁基氢化铝 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (2S)-2-[tert-butyl(dimethyl)silyl]oxy-4-methylidenehex-5-enal
  参考文献：
  名称：

  A new synthesis of the enantiomers of ipsdienol, the pheromone of the IPS bark beetles

  摘要：

  The enantiomers (approximately 96% e.e.) of ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol, 1a) were synthesized from the enantiomers of serine (5) in 16-21% overall yield in 8 steps.

  DOI：

  10.1016/s0040-4020(01)96127-7
• 作为产物：
  描述：

  magnesium,buta-1,3-diene,chloride 、 (R)-缩水甘油酸甲酯 在 CuBr-Me₂S 作用下， 以 四氢呋喃 为溶剂， 以56%的产率得到(S)-2-羟基-4-亚甲基-5-己烯酸甲酯
  参考文献：
  名称：

  A new synthesis of the enantiomers of ipsdienol, the pheromone of the IPS bark beetles

  摘要：

  The enantiomers (approximately 96% e.e.) of ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol, 1a) were synthesized from the enantiomers of serine (5) in 16-21% overall yield in 8 steps.

  DOI：

  10.1016/s0040-4020(01)96127-7

文献信息

• Periselective and enantioselective carbonyl–ene reaction of isoprene with fluoroalkyl glyoxylate catalysed by modified binaphthol–titanium complex: asymmetric catalytic synthesis of enantiomerically pure ipsdienol
  作者：Masahiro Terada、Koichi Mikami

  DOI：10.1039/c39950002391

  日期：——

  The asymmetric reaction of trifluoroethyl glyoxylate 3d with isoprene 4 catalysed by the modified binaphthol–titanium complex 2b provides the ene product 5d in high periselectivity (92%) and complete enantioselectivity, which can be converted to ipsdienol 1, a component of the aggregation pheromone of the bark beetle, genus lps, in enantiomerically pure form.

  三氟乙基乙醇酸酯3d与异戊二烯4在改性联萘酚钛络合物2b催化下发生的不对称反应，以92%的高产率和完全的立体选择性提供了ene产物5d，该产物可以转化为纯对映体形式的ipsdienol 1，即树皮甲虫（lps属）聚集信息素的一个组分。
• Asymmetric Hetero Diels−Alder Reaction Catalyzed by Chiral Cationic Palladium(II) and Platinum(II) Complexes
  作者：Shuichi Oi、Eiji Terada、Kazuei Ohuchi、Tomoko Kato、Yukari Tachibana、Yoshio Inoue

  DOI：10.1021/jo9906680

  日期：1999.11.1

  The hetero Diels-Alder reaction of nonactivated conjugated dienes 1 with arylglyoxals 2 and glyoxylate esters 7 proceeded enantioselectively in the presence of a catalytic amount of cationic chiral BINAP-palladium or -platinum complexes and 3 Angstrom molecular sieves (MS3A). The addition of MS3A effectively improved the enantioselectivity of the reaction. Excellent ee's were obtained from the reactions of 2,3-dimethyl-1,3-butadiene (1a) and 1,3-cyclohexadiene (1d) with dienophiles 2 and 7. The square-planar structure of [Pd(S-BINAP)(PhCN)(2)](PF6)(2) was determined by X-ray diffraction, and a chiral induction model involving the square-planar palladium complex coordinated with BINAP and a dienophile is proposed.