2-chloro-3-cyclohexyl-prop-2-enoic acid methyl ester

• 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: 2-chloro-3-cyclohexyl-prop-2-enoic acid methyl ester
• 英文别名: (Z)-2-chloro-3-cyclohexylacrylic acid methyl ester；methyl (Z)-2-chloro-3-cyclohexylprop-2-enoate
• 化学式: C₁₀H₁₅ClO₂
• 分子量: 202.681
• InChiKey: VFUXLZYZWDCNOC-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2-chloro-3-cyclohexyl-prop-2-enoic acid methyl ester 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以96%的产率得到methyl 5-cyclohexyl-1H-1,2,3-triazole-4-carboxylate
  参考文献：
  名称：

  α-Haloacrylates as acceptors in the [3 + 2] cycloaddition reaction with NaN3: an expedient approach to N-unsubstituted 1,2,3-triazole-4-carboxylates

  摘要：

  通过叠氮化钠与δ-卤代丙烯酸酯的[3 + 2]环加成，证明了一种 N-未取代的 1,2,3-三唑-4-羧酸盐的便捷合成方法。该工艺非常可靠，而且适用于δ-氟、δ-氯、δ-溴和δ-碘丙烯酸酯的范围异常广泛。此外，还说明了选定的 1,2,3-三唑-4-羧酸盐在制备 1,5-二氢-4H-[1,2,3]-三唑-[4,5-c]-喹啉-4-酮方面的潜力。

  DOI：

  10.1039/c3ob42276c
• 作为产物：
  描述：

  2,2-dichloro-3-cyclohexyl-3-hydroxypropionic acid methyl ester 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以62%的产率得到2-chloro-3-cyclohexyl-prop-2-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis of ( Z )-α-chloro-α,β-unsaturated esters with complete stereoselectivity promoted by samarium diiodide

  摘要：

  Stereoselective beta-elimination in alpha,alpha-dichloro-beta-hydroxyesters 2 was achieved by using samarium diiodide, yielding (Z)-alpha-chloro-alpha, beta-unsaturated esters 1. The starting compounds 2 were easily prepared by reaction of the lithium enolate of ethyl dichloroacetate with different aldehydes at -78 degreesC. A mechanism to explain this process is proposed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.101

文献信息

• Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general approach to (Z)-α-haloacrylates
  作者：John Kallikat Augustine、Agnes Bombrun、Srinivasa Venkatachaliah、Anandh Jothi

  DOI：10.1039/c3ob41592a

  日期：——

  An exceptionally stereoselective and general synthesis of (Z)-α-haloacrylates, ready to undergo various synthetic transformations, has been demonstrated from α-haloacetates and aldehydes in a one-pot manner via the titanium-enolate based asymmetric aldol condensation. Besides being an expedient synthetic procedure, the ready availability of diverse α-haloacetates, exceptional stereoselectivity, and high yields make the process a versatile transformation in organic synthesis. The potential of this method in up-scaling operations has been illustrated.

  展示了一种异常立体选择性和通用性合成（Z）-α-卤代丙烯酸酯的方法，该方法通过钛烯醇基催化的不对称 aldol 凝缩反应，采用 α-卤代乙酸酯和醛以一步法进行合成。这种合成方法不仅便捷，而且多样的 α-卤代乙酸酯的可得性、出色的立体选择性和高产率使得该过程在有机合成中具有多功能性。该方法在放大操作中的潜力也得到了展示。
• Synthesis of ( Z )-α-chloro-α,β-unsaturated esters with complete stereoselectivity promoted by samarium diiodide
  作者：José M. Concellón、Mónica Huerta、Ricardo Llavona

  DOI：10.1016/j.tetlet.2004.04.101

  日期：2004.6

  Stereoselective beta-elimination in alpha,alpha-dichloro-beta-hydroxyesters 2 was achieved by using samarium diiodide, yielding (Z)-alpha-chloro-alpha, beta-unsaturated esters 1. The starting compounds 2 were easily prepared by reaction of the lithium enolate of ethyl dichloroacetate with different aldehydes at -78 degreesC. A mechanism to explain this process is proposed. (C) 2004 Elsevier Ltd. All rights reserved.
• α-Haloacrylates as acceptors in the [3 + 2] cycloaddition reaction with NaN3: an expedient approach to N-unsubstituted 1,2,3-triazole-4-carboxylates
  作者：John Kallikat Augustine、Chandrakantha Boodappa、Srinivasa Venkatachaliah

  DOI：10.1039/c3ob42276c

  日期：——

  An expedient synthesis of N-unsubstituted 1,2,3-triazole-4-carboxylates has been demonstrated through [3 + 2] cycloaddition of sodium azide with α-haloacrylates. The process is highly reliable and exhibits an unusually wide scope with respect to α-fluoro-, α-chloro-, α-bromo-, and α-iodoacrylates. The potential of selected 1,2,3-triazole-4-carboxylates in the preparation of 1,5-dihydro-4H-[1,2,3]-triazolo-[4,5-c]-quinolin-4-one has also been illustrated.

  通过叠氮化钠与δ-卤代丙烯酸酯的[3 + 2]环加成，证明了一种 N-未取代的 1,2,3-三唑-4-羧酸盐的便捷合成方法。该工艺非常可靠，而且适用于δ-氟、δ-氯、δ-溴和δ-碘丙烯酸酯的范围异常广泛。此外，还说明了选定的 1,2,3-三唑-4-羧酸盐在制备 1,5-二氢-4H-[1,2,3]-三唑-[4,5-c]-喹啉-4-酮方面的潜力。