cis-1,2-dibutylcyclopropane | 72149-17-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 饱和烃
• 英文名称: cis-1,2-dibutylcyclopropane
• 英文别名: cis-1,2-di-n-butylcyclopropane；(1S,2R)-1,2-dibutylcyclopropane
• CAS: 72149-17-8
• 化学式: C₁₁H₂₂
• 分子量: 154.296
• InChiKey: NFTQIMBYKJVJIT-PHIMTYICSA-N

物化性质

• 沸点：
  190.9±7.0 °C(Predicted)
• 密度：
  0.793±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  顺式-5-癸烯 在 dicarbonyl(η⁵-2,4-cyclopentadien-1-yl)(dimethylsulfonium η-methylide)iron tetrafluoroborate 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 生成 cis-1,2-dibutylcyclopropane
  参考文献：
  名称：

  (.eta.5-C5H5)(CO)2FeCH2S+(CH3)2 BF4-: a methylene transfer reagent for the direct cyclopropanation of alkenes

  摘要：

  DOI：

  10.1021/ja00246a036

文献信息

• Stereodefined Substituted Cyclopropyl Zinc Reagents from Gem-Bismetallics
  作者：Dov Beruben、Ilane Marek、Jean F. Normant、Nicole Platzer

  DOI：10.1021/jo00113a032

  日期：1995.4

  1,1- or n,n-Bismetallic reagents bearing a methoxymethyl ether in the gamma position undergo cyclization at room temperature to give monometalated, diastereoselectively substituted cyclopropanes, The nature of the substituents is crucial for this diastereoselection, a pi-chelation between one metal and a properly located unsaturation, as well as 1,2-strain, are proposed to explain the steric outcome of these reactions.
• Gai, Yonghua; Julia, Marc; Verpeaux, Jean-Noel, Bulletin de la Societe Chimique de France, 1996, vol. 133, # 9, p. 817 - 829
  作者：Gai, Yonghua、Julia, Marc、Verpeaux, Jean-Noel

  DOI：——

  日期：——
• Mechanism-Based Design and Optimization of a Catalytic Electrophilic Cyclopropanation without Diazomethane
  作者：Augustin A. S. W. Tchawou、Mihai Raducan、Peter Chen

  DOI：10.1021/acs.organomet.6b00531

  日期：2017.1.9

  Iodomethylboron compounds, either the trifluoroborate or a boronic ester, cyclopropanate electron-rich olefins and unprotected allylic alcohols with Pd catalysts according to a novel, designed catalytic cycle. Proposed intermediates in a "diverted Heck" mechanism are observed by means of spectroscopic studies and by isolation and X-ray crystallographic characterization, which together with reaction kinetics point to a separation of rate-determining and product-determining steps, and a mechanism-based optimization of the yield, selectivity, and scope of the catalytic electrophilic cyclopropanation. The reaction with crystalline, air-stable, nonhygroscopic, and nontoxic reagents provides an alternative to Simmons Smith-type reactions, as well as cyclopropanation procedures that require the use of diazomethane.
• Cyclic stereocontrol via organobismetallic reagents. Part V. Diastereoselective synthesis of substituted cyclopropyl zinc reagents by the metalla-claisen reaction
  作者：Dov Beruben、Ilane Marek、Lydie Labaudinière、Jean-F. Normant

  DOI：10.1016/s0040-4039(00)77599-x

  日期：1993.4

  The tandem ''Metalla-Claisen - Cyclization'' reaction of a functionalized vinyl lithium derivative allows the preparation of a single isomer of a metallated cyclopropyl ring.
• BRANDT S.; HELQUIST P., J. AMER. CHEM. SOC., 1979, 101, NO 21, 6473-6475
  作者：BRANDT S.、 HELQUIST P.

  DOI：——

  日期：——