5-己烯酸,2-羟基-5-甲基-4-亚甲基-,甲基酯 | 183562-28-9

• 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: 5-己烯酸,2-羟基-5-甲基-4-亚甲基-,甲基酯
• 英文名称: Methyl 2-hydroxy-5-methyl-4-methylene-5-hexenoate
• 英文别名: 5-Hexenoic acid, 2-hydroxy-5-methyl-4-methylene-, methyl ester；methyl 2-hydroxy-5-methyl-4-methylidenehex-5-enoate
• CAS: 183562-28-9
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: JTUGDRHLGFBOLF-UHFFFAOYSA-N

物化性质

• 沸点：
  241.6±20.0 °C(Predicted)
• 密度：
  1.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙醛酸甲酯 、 2,3-二甲基-1,3-丁二烯 在 三甲基铝 、 S-1,1'-联-2-萘酚 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以12%的产率得到5-己烯酸,2-羟基-5-甲基-4-亚甲基-,甲基酯
  参考文献：
  名称：

  A highly chemo- and enantio-selective hetero-Diels–Alder reaction catalysed by chiral aluminium complexes

  摘要：

  A new, highly chemo- and enantio-selective catalytic hetero Diels-Alder reaction of conjugated dienes containing allylic C-H bonds with carbonyl compounds has been developed; with the use of (S)-(-)-BINOL-AlMe (BINOL = 1,1'-bi-2-naphthol) as a catalyst, simple conjugated dienes react with glyoxylate esters, giving the (R)-enantiomer of the hetero-Diels-Alder adduct as the major product with up to 97% ee.

  DOI：

  10.1039/cc9960002373

文献信息

• 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.
• Asymmetric hetero Diels-Alder reactions and ene reactions catalyzed by chiral copper(II) complexes
  作者：Mogens Johannsen、Karl Anker Joergensen

  DOI：10.1021/jo00123a007

  日期：1995.9

  A new copper(II) bisoxazoline-catalyzed reaction of glyoxylate esters with dienes leading to the hetero Diet-Alder product and the ene product in high yield and with a high enantiomeric excess (ee) has been developed. The hetero Diels-Alder product:ene product ratio is in the range 1:0.6 to 1:1.8 and is dependent on both the chiral ligand attached to the metal, the glyoxylate ester, and the reaction temperature. The scope of the copper(II) bisoxazoline-catalyzed reaction of glyoxylate esters with dienes is demonstrated by the reaction of a variety of different dienes with ethyl and isopropyl glyoxylate, and it is shown that a simple substrate such as 1,3-butadiene reacts to give the hetero Diels-Alder product in 55% yield with an ee of 87%. Furthermore, the synthetic application of the reaction is demonstrated by the synthesis of a highly interesting synthon for sesquiterpene lactones in high yield and diastereoselectivity, and with a very high ee from 1,3-cyclohexadiene and ethyl glyoxylate using a copper(II) bisoxazoline as the catalyst. A mechanism for the hetero Diels-Alder reaction, which accounts for the enantioselectivity in the reactions, is proposed.
• A highly chemo- and enantio-selective hetero-Diels–Alder reaction catalysed by chiral aluminium complexes
  作者：Anette Graven、Mogens Johannsen、Karl Anker Jørgensen

  DOI：10.1039/cc9960002373

  日期：——

  A new, highly chemo- and enantio-selective catalytic hetero Diels-Alder reaction of conjugated dienes containing allylic C-H bonds with carbonyl compounds has been developed; with the use of (S)-(-)-BINOL-AlMe (BINOL = 1,1'-bi-2-naphthol) as a catalyst, simple conjugated dienes react with glyoxylate esters, giving the (R)-enantiomer of the hetero-Diels-Alder adduct as the major product with up to 97% ee.