isopropyl 3-oxocyclohex-1-ene-1-carboxylate | 122689-79-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 3-oxocyclohex-1-ene-1-carboxylate
• 英文别名: Propan-2-yl 3-oxocyclohexene-1-carboxylate
• CAS: 122689-79-6
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: CWIIBUQCRSMZEW-UHFFFAOYSA-N

物化性质

• 沸点：
  261.7±29.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isopropyl 3-oxocyclohex-1-ene-1-carboxylate 在 chromium(VI) oxide 、 葡萄糖 、 cultures of Geotrichum candidum 、 phosphate buffer pH: 7.0 、 硫酸 、 hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 48.0h， 生成 (1R)3-氧代环己烷甲酸乙酯
  参考文献：
  名称：

  化学酶促合成构象刚性的谷氨酸类似物

  摘要：

  通过微生物步骤和标准化学方法的结合，由相应的3-酮-环烷基羧酸酯合成了环己烷和谷氨酸的环戊烷衍生的类似物的所有立体异构体。

  DOI：

  10.1016/s0040-4039(00)82278-9
• 作为产物：
  描述：

  isopropyl 1-bromocyclohexanecarboxylate 在 chromium(VI) oxide 、 乙酸酐 作用下， 以 喹啉 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 2.75h， 生成 isopropyl 3-oxocyclohex-1-ene-1-carboxylate
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiopure isopropyl (3R)- and (3S)-3-hydroxycyclohex-1-ene-1-carboxylates and their reduction to isomers of isopropyl 3-hydroxy-cyclohexane-1-carboxylate

  摘要：

  Reduction of an alpha,beta-unsaturated cyclic ketone with Geotrichum candidum affords the corresponding (S)-allylic alcohol, while enantiospecific oxidation of the corresponding racemic alcohols leases the (R)-enantiomer unchanged, giving access to both enantiomeric forms. Subsequent chemical reduction of the double bond of these homochiral allylic alcohol allows all isomers of the corresponding cyclohexanols to be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00152-0

文献信息

• METHOD FOR THE PREPARATION OF ENANTIOMER FORMS OF CIS-CONFIGURED 3-HYDROXYCYCLOHEXANE CARBOXYLIC ACID DERIVATIVES USING HYDROLASES
  申请人：Holla Wolfgang

  公开号：US20070197788A1

  公开（公告）日：2007-08-23

  The present invention relates to a process for preparing chiral non-racemic cis-configured cyclohexanols or cyclohexanol derivatives of the formula (I) Cis-configured hydroxyl-cyclohexane carboxylic acid derivatives of formula (I) are central building blocks or immediate precursors for the medicinally active compounds which allow a therapeutic modulation of the lipid and/or carbohydrate metabolism and are thus suitable for preventing and/or treating type II diabetes, hyperglycemia and artherosclerosis. The cis-configured hydroxyl-cyclohexane carboxylic acid derivatives of formula (I) are central building blocks or immediate precursors for the medicinally active compounds described in the prior art.

  本发明涉及一种制备手性非外消旋顺式环己醇或环己醇衍生物的过程，其化学式为(I)。化学式(I)的顺式羟基环己烷羧酸衍生物是中心构建块或药物活性化合物的直接前体，可用于治疗脂质和/或碳水化合物代谢，因此适用于预防和/或治疗II型糖尿病、高血糖和动脉硬化。化学式(I)的顺式羟基环己烷羧酸衍生物是先前技术中描述的药物活性化合物的中心构建块或直接前体。
• (+)-Camphor Derivative Induced Asymmetric [2 + 2] Photoaddition Reaction
  作者：Guolei Zhao、Chao Yang、Hongnan Sun、Run Lin、Wujiong Xia

  DOI：10.1021/ol203314y

  日期：2012.2.3

  An efficient approach to construct an enantiomerically pure cyclobutane skeleton by means of the chiral auxiliary induced [2 + 2] photoaddition reactions has been described. This asymmetric photoreaction exhibited high diastereoselectivity and provided the photoadducts in excellent yields.

  已经描述了通过手性助剂诱导的[2 + 2]光加成反应构建对映体纯的环丁烷骨架的有效方法。这种不对称的光反应表现出高的非对映选择性，并以优异的产率提供了光加合物。
• Chemoenzymatic synthesis of conformationally rigid glutamic acid analogues
  作者：F. Trigalo、D. Buisson、R. Azerad

  DOI：10.1016/s0040-4039(00)82278-9

  日期：——

  All stereomers of cyclohexane and cyclopentane-derived analogues of glutamic acid have been synthesized from the corresponding 3-keto-cycloalkyl carboxylic acid esters by a combination of microbial steps and standard chemical methods.

  通过微生物步骤和标准化学方法的结合，由相应的3-酮-环烷基羧酸酯合成了环己烷和谷氨酸的环戊烷衍生的类似物的所有立体异构体。
• Chemoenzymatic synthesis of enantiopure isopropyl (3R)- and (3S)-3-hydroxycyclohex-1-ene-1-carboxylates and their reduction to isomers of isopropyl 3-hydroxy-cyclohexane-1-carboxylate
  作者：Laure Fonteneau、Sandra Rosa、Didier Buisson

  DOI：10.1016/s0957-4166(02)00152-0

  日期：2002.4

  Reduction of an alpha,beta-unsaturated cyclic ketone with Geotrichum candidum affords the corresponding (S)-allylic alcohol, while enantiospecific oxidation of the corresponding racemic alcohols leases the (R)-enantiomer unchanged, giving access to both enantiomeric forms. Subsequent chemical reduction of the double bond of these homochiral allylic alcohol allows all isomers of the corresponding cyclohexanols to be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.