2-(1-羟基-1-环己基)-3-丁烯酸乙酯 | 50745-74-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(1-羟基-1-环己基)-3-丁烯酸乙酯
• 英文名称: Ethyl 2-(1-hydroxy-1-cyclohexyl)-3-butenoate
• 英文别名: Ethyl 2-(1-hydroxycyclohexyl)but-3-enoate
• CAS: 50745-74-9
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: KLXGSTPVFORRSI-UHFFFAOYSA-N

物化性质

• 沸点：
  288.0±15.0 °C(Predicted)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-羟基-1-环己基)-3-丁烯酸乙酯 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以100%的产率得到ethyl (E)-4-(1-hydroxycyclohexyl)but-2-enoate
  参考文献：
  名称：

  Studies in the regioselectivity of the vinylogous Reformatsky reaction with ambident electrophiles: reversibility, mechanism, and synthetic utility

  摘要：

  DOI：

  10.1021/jo00222a020
• 作为产物：
  描述：

  反式-2-丁烯酸乙酯 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 2-(1-羟基-1-环己基)-3-丁烯酸乙酯
  参考文献：
  名称：

  改革行动：一，有机锌的提炼和再生产

  摘要：

  DOI：

  10.1016/s0022-328x(00)80642-7

文献信息

• Samarium (II) iodide-induced intermolecular coupling of α,β-unsaturated esters with ketones: reactions of methyl propiolate and ethyl buta-2,3-dienoate with cyclohexanone and its application to synthesis of a terpene carboxylic acid
  作者：Masakazu Sono、Natsuki Doi、Eri Yoshino、Sachiko Onishi、Daiki Fujii、Motoo Tori

  DOI：10.1016/j.tetlet.2013.01.120

  日期：2013.4

  propiolate and ethyl buta-2,3-dienoate with cyclohexanone induced by SmI2 occurred either at α- or β-position to yield different products depending on with or without a proton source. The synthesis of terpenic acid was demonstrated using this reaction.

  SmI 2诱导的丙酸甲酯和2,3-丁二酸丁酸乙酯与环己酮的反应发生在α-位置或β-位置，根据有无质子源产生不同的产物。使用该反应证明了萜烯酸的合成。
• Tandem Aldol-Cyclization Sequence for the Construction of Cyclic Ethers. The Formation of Substituted Tetrahydrofurans
  作者：Paul Galatsis、Scott D. Millan、Patrik Nechala、George Ferguson

  DOI：10.1021/jo00101a024

  日期：1994.11

  The application of a tandem deconjugative aldol-cyclization Sequence for the construction of substituted tetrahydrofurans was examined. The aldol condensation of alkenoates proceeded with alkylation at the alpha-position to generate homoallylic alcohol moieties. These compounds could be induced to cyclize under the influence of iodine via an endo mode. The stereoselectivity for the cyclization occurred in good to excellent fashion. X-ray crystal structure analysis of three of the tetrahydrofurans established unambiguously the product stereochemistry. This was: used to propose a transition structure for the cyclization which correctly predicts the observed product stereochemistry. By this method, virtually all the possible stereoisomers for the substituted tetrahydrofurans can be constructed by judicious choice of aldol product and/or olefin geometry.
• Regioselectivity in the Reformatskii reaction of 4-bromocrotonate. Role of the catalyst and the solvent in the normal vs. abnormal modes of addition to carbonyl substrates
  作者：Leonard E. Rice、M. Craig Boston、Harry O. Finklea、Billy Jo Suder、James O. Frazier、Tomas Hudlicky

  DOI：10.1021/jo00184a042

  日期：1984.5
• RICE, L. E.;BOSTON, M. C.;FINKLEA, H. O.;SUDER, B. J.;FRAZIER, F. O.;HUDL+, J. ORG. CHEM., 1984, 49, N 10, 1845-1848
  作者：RICE, L. E.、BOSTON, M. C.、FINKLEA, H. O.、SUDER, B. J.、FRAZIER, F. O.、HUDL+

  DOI：——

  日期：——
• HUDLICKY, T.;NATCHUS, M. G.;KWART, L. D.;COLWELL, B. L., J. ORG. CHEM., 1985, 50, N 22, 4300-4306
  作者：HUDLICKY, T.、NATCHUS, M. G.、KWART, L. D.、COLWELL, B. L.

  DOI：——

  日期：——