dimethyl 2-hexylcyclopropane-1,1-dicarboxylate | 1110700-57-6

• 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: dimethyl 2-hexylcyclopropane-1,1-dicarboxylate
• 英文别名: Dimethyl 2-hexylcyclopropane-1,1-dicarboxylate
• CAS: 1110700-57-6
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: JPDFSKAONUOGQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 2-hexylcyclopropane-1,1-dicarboxylate 、 N-benzylidene-4-methylaniline oxide 在 ytterbium(III) triflate hydrate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以34%的产率得到
  参考文献：
  名称：

  Advancing the Reactivity of Dimethylcyclopropane-1,1-dicarboxylates via Cross Metathesis

  摘要：

  Cross metathesis of the readily available dimethyl 2-vinylcycloropane-1,1-dicarboxylate with a variety of olefins gave divergent access to new donor-acceptor cyclopropanes bearing a -donor alkenyl substituent. The synthetic utility of these cyclopropanes was shown by their participation in cycloaddition reactions with nitrones to yield the anticipated tetrahydro-1,2-oxazines. Hydrogenation yielded the alkyl-substituted adducts which would be more difficult to access via other means.

  DOI：

  10.1055/s-0033-1340460
• 作为产物：
  描述：

  dimethyl 2-(hex-1-enyl)cyclopropane-1,1-dicarboxylate 在 sodium acetate 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以90%的产率得到dimethyl 2-hexylcyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  Advancing the Reactivity of Dimethylcyclopropane-1,1-dicarboxylates via Cross Metathesis

  摘要：

  Cross metathesis of the readily available dimethyl 2-vinylcycloropane-1,1-dicarboxylate with a variety of olefins gave divergent access to new donor-acceptor cyclopropanes bearing a -donor alkenyl substituent. The synthetic utility of these cyclopropanes was shown by their participation in cycloaddition reactions with nitrones to yield the anticipated tetrahydro-1,2-oxazines. Hydrogenation yielded the alkyl-substituted adducts which would be more difficult to access via other means.

  DOI：

  10.1055/s-0033-1340460

文献信息

• Rhodium-Catalyzed Cyclopropanation of Alkenes with Dimethyl Diazomalonate
  作者：Francisco González-Bobes、Michaël D. B. Fenster、Susanne Kiau、Laxma Kolla、Sergei Kolotuchin、Maxime Soumeillant

  DOI：10.1002/adsc.200800027

  日期：2008.4.7

  α′-tetramethyl-1,3-benzenedipropanoate] to catalyze the cyclopropanation of a wide range of alkenes with malonate-derived carbenoids under mild reaction conditions is reported in this communication. The experimental protocol is remarkably simple, uses readily accessible and stable dimethyl diazomalonate with very low catalyst loading. More importantly, the alkene is employed as a limiting reagent.

  α，α，α'，α'-四甲基-1,3-苯二丙酸酯[Rh 2（esp）2；据报道，esp =α，α，α'，α'-四甲基-1,3-苯二丙酸酯]在温和的反应条件下与丙二酸酯衍生的类胡萝卜素催化多种烯烃的环丙烷化反应。实验方案非常简单，使用容易获得且稳定的重氮丙二酸二甲酯，催化剂的负载量非常低。更重要的是，烯烃被用作限制试剂。
• Design, Preparation, X-ray Crystal Structure, and Reactivity of <i>o</i>-Alkoxyphenyliodonium Bis(methoxycarbonyl)methanide, a Highly Soluble Carbene Precursor
  作者：Chenjie Zhu、Akira Yoshimura、Lei Ji、Yunyang Wei、Victor N. Nemykin、Viktor V. Zhdankin

  DOI：10.1021/ol301268j

  日期：2012.6.15

  The preparation, X-ray structure, and reactivity of new, highly soluble, and reactive iodonium ylides derived from malonate methyl ester and bearing an ortho substituent on the phenyl ring are reported. These new reagents show higher reactivity than common phenyliodonium ylides in the Rh-catalyzed cyclopropanation, C–H insertion, and transylidation reactions under homogeneous conditions.

  报道了衍生自丙二酸酯甲酯且在苯环上带有邻位取代基的新型，高度可溶性和反应性碘鎓的制备，X射线结构和反应性。这些新试剂在均相条件下，在Rh催化的环丙烷化，CH插入和酰化反应中显示出比普通苯基碘鎓碘化物更高的反应性。