ethyl 2-hexylcyclopropanecarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-hexylcyclopropanecarboxylate
• 英文别名: ethyl 2-hexylcyclopropane-1-carboxylate；trans-ethyl 2-hexylcyclopropanecarboxylate；(+/-)-trans-2-hexyl-cyclopropanecarboxylic acid ethyl ester；(+/-)-trans-2-Hexyl-cyclopropancarbonsaeure-aethylester；ethyl (1R,2R)-2-hexylcyclopropane-1-carboxylate
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: JTKYEFCQEMMJTH-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  ethyl 2-hexylcyclopropanecarboxylate 生成 trans-2-hexylcyclopropylcarboxylic acid
  参考文献：
  名称：

  On the Structure of Lactobacillic Acid^1,2

  摘要：

  DOI：

  10.1021/ja01636a020
• 作为产物：
  描述：

  重氮乙酸乙酯 、 辛烯 在 二丁醚 、 铜 作用下， 生成 ethyl 2-hexylcyclopropanecarboxylate
  参考文献：
  名称：

  On the Structure of Lactobacillic Acid^1,2

  摘要：

  DOI：

  10.1021/ja01636a020

文献信息

• Cu and Au Metal-Organic Frameworks Bridge the Gap between Homogeneous and Heterogeneous Catalysts for Alkene Cyclopropanation Reactions
  作者：Avelino Corma、Marta Iglesias、Francesc X. Llabrés i Xamena、Félix Sánchez

  DOI：10.1002/chem.201000278

  日期：2010.8.23

  The copper and gold metal–organic frameworks (MOFs) [Cu3(BTC)2(H2O)3]n, [Cu3(BTC)2] (BTC=benzene‐1,3,5‐tricarboxylate), and IRMOF‐3‐SI‐Au are active and reusable solid catalysts for the cyclopropanation of alkenes with high chemo‐ and diastereoselectivities. This type of material gives better results than previous solid catalysts while working together with the homogeneous catalysts. These MOFs can help

  铜和金-金属有机骨架（MOF）[Cu 3（BTC）2（H 2 O）3 ] n，[Cu 3（BTC）2 ]（BTC =苯-1,3,5-三羧酸盐），和IRMOF-3-SI-Au是活性和可重复使用的固体催化剂，用于具有高化学选择性和非对映选择性的烯烃的环丙烷化反应。当与均相催化剂一起工作时，这种类型的材料比以前的固体催化剂提供更好的结果。这些MOF可以帮助弥合均相和异相催化之间的差距。
• Investigation of ligand steric effects on a highly cis-selective Rh(i) cyclopropanation catalyst
  作者：Marianne Lenes Rosenberg、Eirin Langseth、Alexander Krivokapic、Nalinava Sen Gupta、Mats Tilset

  DOI：10.1039/c1nj20343f

  日期：——

  Four new Rh(I) complexes bearing chelating imine-functionalized N-heterocyclic carbene ligands have been synthesized and characterized. The catalytic activity of these new Rh(I) complexes has been tested in the cyclopropanation reaction between ethyl diazoacetate and styrene. One of the new complexes, having ethyl groups on the ligand N-aryl ring, exhibited a reactivity and a cis-diastereoselectivity that were comparable to our previously reported Rh(I) cyclopropanation catalyst of this type, and a higher yield and cis-diastereoselectivity were obtained at lower catalyst loadings and higher temperatures. The other new Rh(I) complexes were found to be inferior to the previously reported Rh(I) cyclopropanation catalyst. The catalytic study gave important information about the effect that changing the steric requirements of the substituents at the ligand system has on the efficiency and cis-diastereoselectivity of the complexes as cyclopropanation catalysts.

  合成了四种新型Rh(I)配合物，它们带有螯合亚胺功能化的N-杂环卡宾配体，并对这些配合物进行了表征。测试了这些新型Rh(I)配合物在二氮乙酸乙酯和苯乙烯的环丙烷化反应中的催化活性。其中一种新型配合物在配体N-芳基环上具有乙基，其反应活性和顺式立体选择性与先前报道的该类型Rh(I)环丙烷化催化剂相当，并在较低催化剂用量和较高温度下获得了更高的产率和顺式立体选择性。其他新型Rh(I)配合物的性能则不如先前报道的Rh(I)环丙烷化催化剂。这项催化研究提供了重要信息，即改变配体系统上取代基的立体要求对配合物作为环丙烷化催化剂的效率和顺式立体选择性的影响。
• A novel porphyrazine ligand tailored to homogeneous metal catalyzed transformations
  作者：Matteo Parravicini、Luca Vaghi、Giancarlo Cravotto、Norberto Masciocchi、Angelo Maspero、Giovanni Palmisano、Andrea Penoni

  DOI：10.3998/ark.5550190.p008.813

  日期：——

  A novel centrosymmetric porphyrazine (Pz) 1 decorated with pyrazino-dibenzo[ b,f ]azepine units have been prepared via Linstead macrocyclization re action of a dinitrile precursor. Accordingly, the peripheral azepine nitrogen offers a chemical h andle for subsequent functionalizations. Characterization of the metal complexes (MPzs = Metal Porphyrazines) of 1 was accomplished and good catalytic performances

  通过二腈前体的 Linstead 大环化反应制备了一种新型的中心对称四氮杂卟啉 (Pz) 1 装饰有吡嗪并二苯并[ b, f ]氮杂单元。因此，外围氮杂氮为随后的功能化提供了化学通道。完成了 1 的金属配合物（MPzs = 金属四氮杂卟啉）的表征，并在 Cu(II)-和 Co(II)-催化的与重氮乙酸乙酯的环丙烷化反应中获得了良好的催化性能作为测试反应。
• Rhodium Acetate Dimer Immobilized in 1-Butyl-3-methylimidazolium Hexafluorophosphate Ionic Liquid: a Novel and Recyclable Catalytic System for the Cyclopropanation of Alkenes
  作者：J. S. Yadav、B. V. S. Reddy、P. Narayana Reddy

  DOI：10.1002/adsc.200303136

  日期：2004.1

  Alkenes undergo smooth cyclopropanation with ethyl diazoacetate using a catalytic amount of rhodium acetate dimer, Rh2(OAc)4, immobilized in the air- and moisture-stable 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid, [bmim]PF6, to afford cyclopropanecarboxylates in excellent yields with high trans-selectivity. The recovery of the catalyst is facilitated by the hydrophobic nature of [bmim]PF6

  使用催化量的乙酸铑二聚体Rh 2（OAc）4固定在空气和水分稳定的六氟磷酸1-丁基-3-甲基咪唑鎓离子液体[bmim] PF 6中，烯烃与重氮乙酸乙酯进行平滑的环丙烷化反应。以优异的收率和高反选择性得到环丙烷羧酸酯。[bmim] PF 6的疏水性促进了催化剂的回收。回收的含Rh 2（OAc）4的离子液体可重复使用三到五次，但活性只会逐渐降低。
• Highly enantioselective and cis-diastereoselective cyclopropanation of olefins catalyzed by ruthenium complexes of (iminophosphoranyl)ferrocenes
  作者：Vo D.M. Hoang、Pattubala A.N. Reddy、Tae-Jeong Kim

  DOI：10.1016/j.tetlet.2007.09.035

  日期：2007.11

  Chiral (iminophosphoranyl)ferrocenes (1 and 2) are highly efficient ligands to achieve high diastereoselectivity (up to 95/5 dr in favor of the cis-isomer) as well as enantioselectivity (up to 99% ee) in Ru-catalyzed asymmetric cyclopropanation of various olefins. Reversal in diastereoselectivity is found as a function of metal-to-ligand ratio in the reaction of styrene.

  手性（亚氨基磷烷基）二茂铁（1和2）是高效配体，可在Ru催化的不对称环丙烷化中实现高非对映选择性（高达95/5 dr，支持顺式异构体）和对映选择性（高达99％ee）。各种烯烃。发现非对映选择性的逆转是苯乙烯反应中金属与配体比率的函数。