3-cyclohexylacrylic acid methyl ester | 705-95-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-cyclohexylacrylic acid methyl ester
• 英文别名: Cyclohexylacrylsaeure-methylester；methyl 3-cyclohexyl-2-propenoate；methyl 3-cyclohexylpropenoate；methyl 3-cyclohexylacrylate；3-cyclohexyl-acrylic acid methyl ester；3-Cyclohexyl-acrylsaeure-methylester；Methyl 3-cyclohexylprop-2-enoate
• CAS: 705-95-3
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: XKLAFWWDQPGTLE-UHFFFAOYSA-N

物化性质

• 沸点：
  227.1±9.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  3-cyclohexylacrylic acid methyl ester 在 manganese(IV) oxide 、 二异丁基氢化铝 作用下， 以 正己烷 为溶剂， 反应 6.0h， 生成 3-cyclohexyl-2-propenal
  参考文献：
  名称：

  Pd-PHOX 催化剂对脂肪胺与无环二烯的对映选择性分子间加成

  摘要：

  我们报告了一种将脂肪胺催化、对映选择性分子间加成到无环 1,3-二烯的方法。在大多数情况下，在 5 mol% 的带有 PHOX 配体的 Pd 催化剂的存在下，反应在室温或低于室温下有效地进行，生成烯丙胺高达 97:3 er。配体中缺电子膦的存在不仅会导致催化剂更具活性，而且对于在转化中实现高位点选择性也至关重要。

  DOI：

  10.1021/jacs.7b03480
• 作为产物：
  描述：

  3-cyclohexylacrylic acid 在 硫酸 作用下， 以 甲醇 为溶剂， 以87%的产率得到3-cyclohexylacrylic acid methyl ester
  参考文献：
  名称：

  Spirodiketopiperazine-based CCR5 antagonist: Discovery of an antiretroviral drug candidate

  摘要：

  Following the discovery that hydroxylated derivative 3 (Fig. 1) was one of the oxidative metabolites of the original lead 1, it was found that hydroxylated compound 4 possesses higher in vitro anti-HIV potency than the corresponding non-hydroxylated compound 2. Structural hybridation of 4 with the orally available analog 5 resulted in another orally-available spirodiketopiperazine CCR5 antagonist 6a that possesses more favorable pharmaceutical profile for use as a drug candidate. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.109

文献信息

• Palladium-Catalyzed Alkoxycarbonylation of Terminal Alkenes To Produce α,β-Unsaturated Esters: The Key Role of Acetonitrile as a Ligand
  作者：Andrei V. Malkov、Nolwenn Derrien、Maciej Barłóg、Pavel Kočovský

  DOI：10.1002/chem.201304798

  日期：2014.4.14

  A mild protocol has been developed for the PdII‐catalyzed alkoxycarbonylation of terminal olefins to produce α,β‐unsaturated esters with a wide range of substrates. Key features are the use of MeCN as solvent (and/or ligand) to control the reactivity of the intermediate Pd complexes and the combination of CO with O2, which facilitates the CuII‐mediated reoxidation of the Pd0 complex to PdII and prevents

  已开发出一种温和的方案，用于末端烯烃的Pd II催化的烷氧羰基化反应，以生产具有多种底物的α，β-不饱和酯。关键特征是使用MeCN作为溶剂（和/或配体）来控制中间Pd配合物的反应性，以及CO与O 2的组合，这有助于Cu II介导的Pd 0配合物向Pd II和Pd II的再氧化。防止双羰基化。
• Metal‐Free Directed C−H Borylation of Pyrroles
  作者：Zheng‐Jun Wang、Xiangyang Chen、Lei Wu、Jonathan J. Wong、Yong Liang、Yue Zhao、Kendall N. Houk、Zhuangzhi Shi

  DOI：10.1002/anie.202016573

  日期：2021.4.6

  conspicuously underdeveloped. Here, we develop a general strategy for the site‐selective C−H borylation of pyrroles by using only BBr3 directed by pivaloyl groups, avoiding the use of any metal. The site‐selectivity is generally dominated by chelation and electronic effects, thus forming diverse C2‐borylated pyrroles against the steric effect. The formed products can readily engage in downstream transformations

  仍然明显缺乏开发能以选择性，实用，低成本和环境友好的模式快速构建复杂的有机硼酸酯的稳健策略。在这里，我们通过仅使用由新戊酰基引导的BBr 3避免了使用任何金属，为吡咯的位点选择性CH硼化开发了一种通用策略。通常，位点选择性主要受螯合和电子效应的影响，因此形成了多种C2硼化的吡咯，以抵抗空间效应。成型产品可以很容易地参与下游转型，从而实现了逐步经济的过程来获得立普妥（Lipitor）等药物。DFT计算（wB97X-D）证明了该反应的首选位置选择性。
• Chiral Magnesium(II) Binaphtholates as Cooperative Brønsted/Lewis Acid-Base Catalysts for the Highly Enantioselective Addition of Phosphorus Nucleophiles to α,β-Unsaturated Esters and Ketones
  作者：Manabu Hatano、Takahiro Horibe、Kazuaki Ishihara

  DOI：10.1002/anie.201300938

  日期：2013.4.22

  cooperative Brønsted/Lewis acid–base supramolecular catalysts formed in situ from simple chiral magnesium(II) binaphtholate aqua complexes promoted the highly enantioselective 1,4‐hydrophosphinylation of α,β‐unsaturated esters with diaryl phosphine oxides and 1,2‐hydrophosphonylation of α,β‐unsaturated ketones with dialkyl phosphites (see scheme).

  一点点合作就可以走很长一段路：由简单的手性镁（II）二萘甲酸酯水配合物原位形成的Brønsted/ Lewis酸碱超分子合作催化剂促进了α，β-不饱和酯与二芳基膦的高度对映选择性1，，4-氢膦化。 α，β-不饱和酮的三价氧化物和1,2-氢膦酰基化与亚磷酸二烷基酯（参见方案）。
• Reversal of enantioselective Friedel–Crafts C3-alkylation of pyrrole by slightly tuning the amide units of N,N′-dioxide ligands
  作者：Yulong Zhang、Na Yang、Xiaohua Liu、Jing Guo、Xiying Zhang、Lili Lin、Changwei Hu、Xiaoming Feng

  DOI：10.1039/c4cc10055g

  日期：——

  Reversal enantioselective Friedel-Crafts alkylation of pyrrole with ligands derived from the same type of chiral source of L-ramipril, by slightly tuning the amide units has been realized.

  使用与L-雷米普利相同类型的手性源衍生的配体，通过轻微调整酰胺单元，实现了对吡咯的反向对映选择性Friedel-Crafts烷基化。
• Triphenylphosphine oxide-catalyzed stereoselective poly- and dibromination of unsaturated compounds
  作者：Tian-Yang Yu、Yao Wang、Xiu-Qin Hu、Peng-Fei Xu

  DOI：10.1039/c4cc02847c

  日期：——

  A novel PPh3O catalyzed bromophosphonium salt-mediated dibromination of alpha,beta-unsaturated esters and beta,gamma-unsaturated alpha-ketoesters has been developed. The products were obtained with good to excellent yields and excellent diastereoselectivities. This dibromination reaction is a good complement to the field of dibromination.

  已经开发出新颖的PPh 3 O催化的溴phosph盐介导的α，β-不饱和酯和β，γ-不饱和α-酮酸酯的二溴化。获得的产物具有良好至优异的产率和优异的非对映选择性。该二溴化反应是对二溴化领域的良好补充。