(R)-3-methyl-2-cyclohexenyl acetate | 115073-43-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-3-methyl-2-cyclohexenyl acetate
• 英文别名: (R)-(+)-seudenol acetate；(R)-3-methylcyclohex-2-enyl acetate；[(1R)-3-methylcyclohex-2-en-1-yl] acetate
• CAS: 115073-43-3
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: LGVFVTJGGYGQOS-SECBINFHSA-N

物化性质

• 沸点：
  192.5±29.0 °C(predicted)
• 密度：
  0.98±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-methyl-2-cyclohexenyl acetate 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 4.5h， 以91%的产率得到(1R)-3-甲基环己-2-烯-1-醇
  参考文献：
  名称：

  Mori, Kenji; Ogoche, Jondiko I.J., Liebigs Annalen der Chemie, 1988, p. 903 - 906

  摘要：

  DOI：
• 作为产物：
  描述：

  (3-甲基-1-环己-2-烯基)乙酸酯 生成 (R)-3-methyl-2-cyclohexenyl acetate
  参考文献：
  名称：

  MORI, KENJI;OGOCHE, JONDIKO I. J., LIEBIGS ANN. CHEM.,(1988) N 9, C. 903-905

  摘要：

  DOI：

文献信息

• Discovery and Design of Family VIII Carboxylesterases as Highly Efficient Acyltransferases
  作者：Henrik Müller、Simon P. Godehard、Gottfried J. Palm、Leona Berndt、Christoffel P. S. Badenhorst、Ann‐Kristin Becker、Michael Lammers、Uwe T. Bornscheuer

  DOI：10.1002/anie.202014169

  日期：2021.1.25

  water, which enabled the synthesis of the drug moclobemide from methyl 4‐chlorobenzoate and 4‐(2‐aminoethyl)morpholine (ca. 20 % conversion). We solved the crystal structure of EstCE1 and detailed structure–function analysis revealed a three‐amino acid motif important for promiscuous acyltransferase activity. Introducing this motif into an esterase without acetyltransferase activity transformed a “hydrolase”

  混杂的酰基转移酶活性是某些水解酶优先催化酰基转移而不是水解的能力，即使在大量水中也是如此。然而，对映选择性差、转移效率低、产物水解显着以及底物范围有限等缺点使其应用存在相当大的缺陷。通过对几种水解酶进行基于活性的筛选，我们鉴定出第八家族羧酸酯酶 EstCE1 是一种前所未有的高效酰基转移酶。EstCE1 催化水中胺的不可逆酰胺化和氨甲酰化，从而能够从 4-氯苯甲酸甲酯和 4-(2-氨基乙基)吗啉合成药物吗氯贝胺（转化率约 20%）。我们解析了 EstCE1 的晶体结构，详细的结构功能分析揭示了一个对混杂酰基转移酶活性很重要的三氨基酸基序。将该基序引入没有乙酰转移酶活性的酯酶中，将“水解酶”转化为“酰基转移酶”。
• Enzyme- and Ruthenium-Catalyzed Dynamic Kinetic Resolution of Functionalized Cyclic Allylic Alcohols
  作者：Richard Lihammar、Renaud Millet、Jan-E. Bäckvall

  DOI：10.1021/jo402086z

  日期：2013.12.6

  Enantioselective synthesis of functionalized cyclic allylic alcohols via dynamic kinetic resolution has been developed. Cyclopentadienylruthenium catalysts were used for the racemization, and lipase PS-IM or CALB was employed for the resolution. By optimization of the reaction conditions the formation of the enone byproduct was minimized, making it possible to prepare a range of optically active functionalized

  已经开发了通过动态动力学拆分的功能化环状烯丙基醇的对映选择性合成。环戊二烯基钌催化剂用于消旋，脂肪酶PS-IM或CALB用于拆分。通过优化反应条件，将烯酮副产物的形成减至最少，从而有可能以良好的收率和较高的ee值制备一系列光学活性的官能化烯丙基醇。
• Enzymatic Kinetic Resolution of 2-Cyclohexen-1-ol Derivatives
  作者：Hisahiro Hagiwara、Takashi Nakano、Hisashi Uda

  DOI：10.1246/bcsj.66.3110

  日期：1993.10

  Optically active (S)-2-cyclohexen-1-ol derivatives and their enantiomeric (R)-acetates have been obtained in high enantiomeric excesses by enzymatic kinetic acetylation catalyzed by lipase AK.

  光学活性(S)-2-cyclohexen-1-ol衍生物及其酶(R)-乙酸盐已通过AC lipase催化酶动态乙酸化获得高酶过剩。
• Lipase-catalyzed irreversible transesterifications using enol esters as acylating reagents: preparative enantio- and regioselective syntheses of alcohols, glycerol derivatives, sugars and organometallics
  作者：Yi Fong. Wang、James J. Lalonde、Milagros. Momongan、David E. Bergbreiter、Chi Huey. Wong

  DOI：10.1021/ja00229a041

  日期：1988.10
• The Candida antarctica lipase B catalysed kinetic resolution of seudenol in non-aqueous media of controlled water activity
  作者：Christian Orrenius、Torbjörn Norin、Karl Hult、Giacomo Carrea

  DOI：10.1016/0957-4166(95)00399-1

  日期：1995.12

  For further investigation of the kinetic resolutions in transesterification reactions with the highly enantioselective Candida antarctica lipase B, an easy to study model reaction with one typical substrate, the Douglas Fir Beetle pheromone 3-methyl-2-cyclohexen-1-ol (Seudenol), was developed. The influence of the nature of the solvent and thermodynamic water activity was studied. Initial rates showed constant or progressively increasing values with increasing water activity. Enantioselectivity depended on the choice of solvent and descended in most cases with increasing water activity. No general correlations of enantioselectivity or activity with physicochemical constants of the solvent were found. However, at a water activity of 0.11 a tendency toward optimum hydrophobicity (i.e log P approximate to 2) for enantioselectivity was observed. Enantiomeric ratios were in the range 8-32.