1-cyclobutylidenespiro<3.3>heptane | 118558-77-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: 1-cyclobutylidenespiro<3.3>heptane
• 英文别名: 1-cyclobutylidene-spiro[3.3]heptane；3-Cyclobutylidenespiro[3.3]heptane
• CAS: 118558-77-3
• 化学式: C₁₁H₁₆
• 分子量: 148.248
• InChiKey: QRRFDIXHRBPHGW-UHFFFAOYSA-N

物化性质

• 沸点：
  219.6±7.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-cyclobutylidenespiro<3.3>heptane 在 氢氧化钾 、 一水合肼 、 pyridinium chlorochromate 、 锌 作用下， 以 乙醚 、 二氯甲烷 、 二乙二醇 为溶剂， 反应 28.5h， 生成 (M)-(-)-trispiro[3.0.0.3.2.2]tridecane
  参考文献：
  名称：

  Helical primary structures of four-membered rings: (M)-trispiro[3.0.0.3.2.2]tridecane

  摘要：

  The synthesis of (NI)-trispiro[3.0.0.3.2.2]tridecane [(M)-4], the first hydrocarbon with a helical primary structure of four-membered rings, is described. Key step is the kinetic resolution of a cyclobutanone through reduction with bakers' yeast. As compared to its analogue of three-membered rings, (M)-trispiro[2.0.0.2.1.1]nonane [(M)-1], the specific rotation of (M)-4 is cut in three. According to molecular mechanics calculations this could be due to a potential to adopt different conformations, not given in (M)-1, and to the fact, that (M)-4 describes a distinctly shorter section of a helix than (M)-1. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00617-3
• 作为产物：
  描述：

  螺[3.3]庚烷-1-酮 以86%的产率得到
  参考文献：
  名称：

  Fitjer Lutz, Kanschik Andreas, Majewski Marita, Tetrahedron, 50 (1994) N 37, S 10867-10878

  摘要：

  DOI：

文献信息

• Synthesis and rearrangement of dispiro[3.1.3.2]-, dispiro[3.0.3.3]- and dispiro[3.0.4.2]undecanes- new entries to [3.3.3]propellanes
  作者：Lutz Fitjer、Andrew Kanschik、Marita Majewski

  DOI：10.1016/s0040-4020(01)85699-4

  日期：1994.1

  The dispiroketones 4–6 have been synthesized and rearranged by treatment with acids yielding the bicyclic enone 36 under kinetic control and the [3.3.3]propellane 37 under thermodynamic control. The corresponding alcohols 10–12 all yield the [3.3.3]propellane 41. The rearrangement of [7,7-D2]-12 to [8,8-D2]-41 proceeds stereospecifically and points to dispirane 42 as potential precursor of (6±)-modhephene

  通过使用酸处理合成并重新排列了双螺酮4-6，在动力学控制下生成了双环烯酮36，在热力学控制下生成了[3.3.3]丙炔37。相应的醇10-12均产生[3.3.3]丙炔41。[7,7-d的重新排列2 ] - 12至[8,8-d 2 ] - 41点进行立体专一性和指向dispirane 42如（6±）-modhephene潜在前体43。同样，双螺环烷44和46是（±）-异丁烯45的潜在前体。
• Towards a synthesis of (±)modhephene via cascade rearrangement: Synthesis and rearrangement of dispiro[3.0.4.2]undecanes to [3.3.3]propellanes
  作者：Lutz Fitjer、Marita Majewski、Andreas Kanschik

  DOI：10.1016/s0040-4039(00)80271-3

  日期：1988.1

  The dispiro [3.0.4.2] undecanes 2 and 6 undergo cascade rearrangements yielding the [3.3.3]propellanes 3 and 7, respectively. The rearrangement of 6 proceeds regiospecifically and renders 9 a promising candidate for a direct conversion to (±)modhephene 10.

  双螺[3.0.4.2]十一烷2和6经历级联重排，分别产生[3.3.3]丙炔3和7。6的重排以区域特异性进行，并且9成为直接转化为（±）苯二酚10的有希望的候选者。
• Fitjer Lutz, Kanschik Andreas, Majewski Marita, Tetrahedron, 50 (1994) N 37, S 10867-10878
  作者：Fitjer Lutz, Kanschik Andreas, Majewski Marita

  DOI：——

  日期：——
• FITJER, LUTZ;MAJEWSKI, MARITA;KANSCHIK, ANDREAS, TETRAHEDRON LETT., 29,(1988) N 11, 1263-1264
  作者：FITJER, LUTZ、MAJEWSKI, MARITA、KANSCHIK, ANDREAS

  DOI：——

  日期：——
• Helical primary structures of four-membered rings: (M)-trispiro[3.0.0.3.2.2]tridecane
  作者：Lutz Fitjer、Ralf Gerke、Jörg Weiser、Gabor Bunkoczi、Judit E Debreczeni

  DOI：10.1016/s0040-4020(03)00617-3

  日期：2003.6

  The synthesis of (NI)-trispiro[3.0.0.3.2.2]tridecane [(M)-4], the first hydrocarbon with a helical primary structure of four-membered rings, is described. Key step is the kinetic resolution of a cyclobutanone through reduction with bakers' yeast. As compared to its analogue of three-membered rings, (M)-trispiro[2.0.0.2.1.1]nonane [(M)-1], the specific rotation of (M)-4 is cut in three. According to molecular mechanics calculations this could be due to a potential to adopt different conformations, not given in (M)-1, and to the fact, that (M)-4 describes a distinctly shorter section of a helix than (M)-1. (C) 2003 Elsevier Science Ltd. All rights reserved.