2-chloro-2-cyclohexyl-prop-2-enoic acid isopropyl ester | 727652-80-4

• 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-2-cyclohexyl-prop-2-enoic acid isopropyl ester
• 英文别名: isopropyl (Z)-2-chloro-3-cyclohexylacrylate；propan-2-yl (Z)-2-chloro-3-cyclohexylprop-2-enoate
• CAS: 727652-80-4
• 化学式: C₁₂H₁₉ClO₂
• 分子量: 230.735
• InChiKey: DAGPGCIRPKMSGO-FLIBITNWSA-N

物化性质

• 沸点：
  298.5±13.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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-2-cyclohexyl-prop-2-enoic acid isopropyl ester 在 氢氧化钾 、 水 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以89%的产率得到(Z)-2-chloro-3-cyclohexylacrylic acid
  参考文献：
  名称：

  Stereoselective synthesis of (Z)-α-haloacrylic acid derivatives, and (Z)-haloallylic alcohols from aldehydes and trihaloesters or amides promoted by Rieke manganese

  摘要：

  描述了一种Mn*-促进的顺序反应过程，旨在合成(Z)-α-卤代-α,β-不饱和酯或酰胺。在这两种情况下，该过程均具有完全的Z立体选择性。此外，从源自吗啉的(Z)-α-卤代-α,β-不饱和酰胺或酯中，能够容易地制备(Z)-α-氯代-α,β-不饱和酮、羧酸和(Z)-卤代烯醇。提出了一种机制来解释观察到的顺序过程和立体选择性。

  DOI：

  10.1039/b803449d
• 作为产物：
  描述：

  二氯乙酸异丙酯 在 samarium diiodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.17h， 生成 2-chloro-2-cyclohexyl-prop-2-enoic acid isopropyl 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

• Stereoselective synthesis of (Z)-α-haloacrylic acid derivatives, and (Z)-haloallylic alcohols from aldehydes and trihaloesters or amides promoted by Rieke manganese
  作者：José M. Concellón、Humberto Rodríguez-Solla、Pamela Díaz

  DOI：10.1039/b803449d

  日期：——

  A Mn*-promoted sequential process directed toward the synthesis of (Z)-α-halo-α,β-unsaturated esters or amides is described. In both cases, the process takes place with complete Z-stereoselectivity. In addition, (Z)-α-chloro-α,β-unsaturated ketones and carboxylic acids, and (Z)-haloallylic alcohols were readily prepared from (Z)-α-halo-α,β-unsaturated amides derived from morpholine, or esters. A mechanism has been proposed to explain the sequential process and the stereoselectivity observed.

  描述了一种Mn*-促进的顺序反应过程，旨在合成(Z)-α-卤代-α,β-不饱和酯或酰胺。在这两种情况下，该过程均具有完全的Z立体选择性。此外，从源自吗啉的(Z)-α-卤代-α,β-不饱和酰胺或酯中，能够容易地制备(Z)-α-氯代-α,β-不饱和酮、羧酸和(Z)-卤代烯醇。提出了一种机制来解释观察到的顺序过程和立体选择性。
• Stereoselective Olefination Reactions Promoted by Rieke Manganese
  作者：José Concellón、Humberto Rodríguez-Solla、Vicente del Amo、Pamela Díaz

  DOI：10.1055/s-0029-1216880

  日期：2009.8

  applied to develop a novel and direct synthesis of (E)-α,β-unsaturated esters or amides and (Z)-α,β-unsaturated α-halo esters and α-choroamides through a Mn*-mediated sequential olefination protocol of aldehydes with dichloro esters or amides and trihalo esters or trichloroamides, respectively. manganese - elimination reactions - stereoselectivity - α,β-unsaturated esters - α,β-unsaturated amides - metalation

  提出了使用廉价的无毒金属锰进行立体选择性β-消除反应并促进醛的顺序烯化反应以获得α，β-不饱和酯和酰胺的优势的研究。使用活性锰（Mn *）作为金属化剂进行了各种消除反应，所有这些反应均具有完全的立体选择性和高收率的特征。锰的这种能力已被用于开发通过Mn *-直接合成（E）-α，β-不饱和酯或酰胺与（Z）-α，β-不饱和α-卤代酯和α-氯酰胺的新颖而直接的合成方法。介导的醛分别与二氯酯或酰胺和三卤代酯或三氯酰胺的顺序烯烃化方案。 锰-消除反应-立体选择性-α，β-不饱和酯-α，β-不饱和酰胺-金属化
• 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.